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小木虫论坛-学术科研互动平台» 网络生活区» 有奖问答 » 有奖问答完结子版 » 丙烯酸（丙烯酸甲酯）与己二胺形成酰胺的反应条件？
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昆仑雪狼

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浪荡子

[交流] 丙烯酸（丙烯酸甲酯）与己二胺形成酰胺的反应条件？

我最近在做实验，这个反应条件一直无法敲定，感觉是很容易进行的反应，可是很没有把握，望这方面的大侠们多多赐教啊。
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1楼2009-03-03 21:20:12
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120101405

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帮你找找先关资料确认一下
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谦逊求教才能更进一步
2楼2009-03-03 21:39:31
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yiyunlai

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我也正在模索啊!有机会再交流!
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3楼2009-03-03 22:27:15
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昆仑雪狼

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浪荡子
希望大侠们踊跃点，让暴风雨来得更猛烈些吧！！
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4楼2009-03-04 08:46:51
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xiaomaguohe

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5楼2009-03-04 09:03:30
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leonumn

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昆仑雪狼(金币+3,VIP+0):谢谢你，能给个具体的参考文献不？或者它的出处，真的很感谢 3-4 11:05
CH2=CHCOOH  +  NH2(CH2)6NH2 -------->

(1) DCC or DIC or EDC  (rt)
(2) HBTU-NMM or HCTU-NMM(rt)
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6楼2009-03-04 09:05:38
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leonumn

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CH2=CHCOOH  +  SOCl2 ----------->  CH2=CHCO-Cl    +   NH2(CH2)6NH2 -------->

CH2=CHCONH(CH2)6NH2
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7楼2009-03-04 09:08:25
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leonumn

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昆仑雪狼(金币+6,VIP+0):真的很感谢，呵呵，我是在Ti表面修饰时用的，但反应条件剧烈的话就会影响其他的，呵呵 3-5 10:26
我是做肽合成的, 着种缩合反应是经典的,
http://en.wikipedia.org/wiki/Carbodiimide

Carbodiimide
From Wikipedia, the free encyclopedia
Jump to: navigation, search
A carbodiimide is a functional group consisting of the formula N=C=N. Carbodiimides hydrolyze to form ureas, which makes them rarely found in nature.

Contents [hide]
1 Carbodiimide formation
2 Uses of carbodiimides
2.1 Amide formation mechanism
3 DCC
4 DIC
5 EDC
5.1 References
5.2 External links



[edit] Carbodiimide formation
Carbodiimides are formed by dehydration of ureas or from thioureas.


[edit] Uses of carbodiimides
In synthetic organic chemistry, compounds containing the carbodiimide functionality are dehydration agents and are often used to activate carboxylic acids towards amide or ester formation. Additives, such as N-hydroxybenzotriazole or N-hydroxysuccinimide, are often added to increase yields and decrease side reactions.


Carbodiimides can also react with amines to form guanidines.


[edit] Amide formation mechanism
The formation of an amide using a carbodiimide is straightforward, but with several side reactions complicating the subject. The acid 1 will react with the carbodiimide to produce the key intermediate: the O-acylisourea 2, which can be viewed as a carboxylic ester with an activated leaving group. The O-acylisourea will react with amines to give the desired amide 3 and urea 4.

The side reaction of the O-acylisourea 2 produce both desired and undesired products. The O-acylisourea 2 can react with an addition carboxylic acid 1 to give a acid anhydride 5, which can react further to give the desired amide 3. The main undesired reaction pathway involves the rearrangement of the O-acylisourea 2 to the stable N-acylurea 6. The use of solvents with low-dielectric constants such as dichloromethane or chloroform can minimize this side reaction.



[edit] DCC

Structure of DicyclohexylcarbodiimideMain article: Dicyclohexylcarbodiimide
DCC (acronym for N,N'-dicyclohexylcarbodiimide) was one of the first carbodiimides developed. It is widely used for amide and ester formation, especially for solid-phase peptide synthesis. DCC has achieved popularity mainly because of its high yielding amide coupling reactions and the fact that it is quite inexpensive.

However, DCC does have some serious drawbacks, and its use is often avoided unless necessary, for several reasons:

The byproduct N,N'-dicyclohexylurea is mostly removed by filtration, but trace amounts remain and are often difficult to remove.
DCC is incompatible with traditional solid-phase peptide synthesis. The formed N,N'-dicyclohexylurea is mostly insoluble and is difficult to separate from the peptide resin.
DCC is a potent allergen, repeated contact with skin increases the probability of sensitization to the compound. Clinical reports of individuals who cannot enter rooms where peptide coupling agents are used have been reported.

[edit] DIC

Structure of N,N'-DiisopropylcarbodiimideMain article: N,N'-Diisopropylcarbodiimide
DIC (acronym for N,N'-diisopropylcarbodiimide) was developed as an alternative to DCC. DIC is identical to DCC in nearly every way except:

As a liquid, DIC is easier to handle than DCC (which is a waxy solid).
The product, N,N'-diisopropylurea, is soluble in organic solvents and is easily removed by extraction. Hence, DIC is more often used in solid-phase synthesis.
DIC is far less likely than DCC to cause an allergic reaction.

[edit] EDC
EDC

IUPAC name  [show]
1-ethyl-3-(3-dimethyl
aminopropyl) carbodiimide
hydrochloride
Identifiers
CAS number 25952-53-8
SMILES  [show]
CCN=C=NCCCN(C)C
Properties
Molecular formula C8H17N3 * HCl
Molar mass 191.70 g/mol
Melting point 110-114 °C<

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox references
EDC (also EDAC or EDCI, acronyms for 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride) is a water soluble carbodiimide which is typically employed in the 4.0-6.0 pH range. It is generally used as a carboxyl activating agent for the coupling of primary amines to yield amide bonds. Additionally, EDC can also be used to activate phosphate groups. Common uses for this carbodiimide include peptide synthesis, protein crosslinking to nucleic acids and preparation of immunoconjugates. EDC is often used in combination with N-hydroxysuccinimide (NHS) or sulfo-NHS to increase coupling efficiency or create a stable amine-reactive product.

EDC also used in organic chemistry to couple a carboxylic acid to alcohol using DMAP as a catalyst.


[edit] References
Nakajima, N; Ikada, Y; Bioconjug Chem. 1995, 6(1), 123-130. Abstract http://dx.doi.org/10.1021%2Fbc00031a015
Skotnicki, S; Tetrahedron Lett. 1994, 35(2), 197-200. [1]
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8楼2009-03-04 12:15:08
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huang1987

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金属有机之烂漫小猪
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昆仑雪狼(金币+1,VIP+0):谢谢，这个我知道的，但还是要奖励你的参与！ 3-5 10:27
先与SOCl2反应 再和乙二胺反应
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有爱才有希望！
9楼2009-03-04 12:24:23
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昆仑雪狼

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浪荡子
求助结束！！
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10楼2009-03-05 14:58:23
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