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36650

Sigma-Aldrich

N,N′-二环己基碳二亚胺

≥99.0% (GC), for peptide synthesis

同義詞:

DCC

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About This Item

線性公式:
C6H11N=C=NC6H11
CAS號碼:
分子量::
206.33
Beilstein:
610662
EC號碼:
MDL號碼:
分類程式碼代碼:
12352000
PubChem物質ID:
NACRES:
NA.22

product name

N,N′-二环己基碳二亚胺, puriss., ≥99.0% (GC)

等級

puriss.

品質等級

化驗

≥99.0% (GC)

形狀

solid

反應適用性

reaction type: Coupling Reactions

bp

122-124 °C/6 mmHg (lit.)

mp

32.0-37.0 °C
34-35 °C (lit.)

溶解度

methylene chloride: 0.1 g/mL, clear, colorless

應用

peptide synthesis

SMILES 字串

C1CCC(CC1)N=C=NC2CCCCC2

InChI

1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2

InChI 密鑰

QOSSAOTZNIDXMA-UHFFFAOYSA-N

基因資訊

human ... EPHX2(2053)
mouse ... Ephx2(13850)

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一般說明

DCC是一种有机化合物,已广泛用作肽合成中的偶联剂。它还用作制备酰胺、酯、腈和酸酐的有效脱水剂。在DCC和二甲基亚砜(DMSO)的存在下,可以通过Moffatt氧化反应将醇转化为醛和酮。

應用

DCC可用于促进7-((丁基二甲基甲硅烷基)氧基)庚-2,4-二炔-1-醇与丙炔酸发生酯化反应并形成7-((丁基二甲基甲硅烷基)氧基)庚-2,4-二炔基-1-丙炔酸酯。
它也可以用于合成:
  • 通过与2-苯基乙烯基和2-(4-硝基苯基)乙烯基异硫氰酸酯发生[2+2]环加成反应形成1,3-Thiazetedine衍生物。
  • 通过与苯甲酰异硫氰酸酯发生[4+2]环加成反应形成1,3,5-恶二嗪-4-硫酮。
  • 在芳族(或杂芳族)羧酸存在的条件下,通过与(N--异氰脒基)三苯基膦反应,形成空间位阻1,3,4-恶二唑衍生物。

其他說明

偶联剂,用于脱水等。可修饰牛心脏线粒体转氢酶;抑制 F1F0-ATP 酶和其他质子转移酶

象形圖

Skull and crossbonesCorrosion

訊號詞

Danger

危險分類

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1

儲存類別代碼

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

水污染物質分類(WGK)

WGK 3

閃點(°F)

235.4 °F - closed cup

閃點(°C)

113 °C - closed cup

個人防護裝備

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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分析證明 (COA)

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存取文件庫

Review of synthesis of 1, 3, 4-oxadiazole derivatives.
Patel K D, et al.
Synthetic Communications, 44(13), 1859-1875 (2014)
Light-dependent chemical modification of thylakoid membrane protein with carboxyl-directed reagents.
J A Laszlo et al.
Archives of biochemistry and biophysics, 215(2), 571-581 (1982-05-01)
R M Pennington et al.
The Journal of biological chemistry, 256(17), 8963-8969 (1981-09-10)
Dicyclohexylcarbodiimide (DCCD) inhibits the reduction of oxidized 3-acetylpyridine adenine dinucleotide (AcPyAD+) by NADPH catalyzed by purified and bovine heart submitochondrial particle transhydrogenase. Kinetic studies demonstrate that the modification of 1 residue results in complete inactivation. Both transhydrogenase preparations were labeled
M. Solioz
Trends in Biochemical Sciences, 9, 309-309 (1984)
Dicyclohexylcarbodiimide (DCC)
Kvasnica M
Synlett, 2007(14), 2306-2307 (2007)

文章

In principle, the seemingly simple formation of a peptide bond can be accomplished using all the procedures available in organic chemistry for the synthesis of carboxylic acid amides. However, due to the presence of various functional groups in natural and unnatural amino acids and particularly the requirement for full retention of chiral integrity, the coupling of amino acids and peptides under mild conditions can be challenging. A plethora of coupling reagents has been developed superseding each other in efficiency and suitability for specific applications (e.g., solid-phase peptide synthesis or fragment condensation).

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