N-(trans-cinnamoyl)-methionine methyl ester | 127750-59-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(trans-cinnamoyl)-methionine methyl ester
• 英文别名: N-Cinnamoyl-L-methionine methyl ester；methyl (2S)-4-methylsulfanyl-2-[[(E)-3-phenylprop-2-enoyl]amino]butanoate
• CAS: 127750-59-8
• 化学式: C₁₅H₁₉NO₃S
• 分子量: 293.387
• InChiKey: WYVOPVXEPMYEBC-XEHSLEBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(trans-cinnamoyl)-methionine methyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以92%的产率得到(S)-4-Methylsulfanyl-2-[(E)-(3-phenyl-acryloyl)amino]-butyric acid
  参考文献：
  名称：

  Efficient peptide coupling method of conjugated carboxylic acids with methyl ester amino acids hydrochloride. Application to the synthesis of Fa-Met, an important enzymatic substrate

  摘要：

  Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate reagent (BOP) serves as an efficient and versatile coupling reagent for the coupling Of Conjugated carboxylic acid with methyl ester amino acids hydrochloride allowing the synthesis of various Substituted amino acid derivatives in high chemical yields of up to 90%. The usefulness of this method is illustrated in the synthesis of Fa-Met, an important enzymatic substrate. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.082
• 作为产物：
  描述：

  肉桂酸 、 L-蛋氨酸甲酯盐酸盐 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到N-(trans-cinnamoyl)-methionine methyl ester
  参考文献：
  名称：

  Carboxamidation of carboxylic acids with 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) without bases

  摘要：

  Formation of carboxamides of a variety of carboxylic acids with the coupling reagent BBDI is described, This procedure permits a one pot and simple operation without the need of any bases and no base was required for even use of amine hydrochlorides. In addition, an approach to BBDI-catalyzed carboxamidation is examined. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.094

文献信息

• ARUTYUNYAN, A. A.;MELIK-OGADZHANYAN, R. G.;ALAVERDOVA, L. G.;PAPOYAN, S. +, XIM.-FARMATS. ZH., 23,(1989) N0, S. 1223-1226
  作者：ARUTYUNYAN, A. A.、MELIK-OGADZHANYAN, R. G.、ALAVERDOVA, L. G.、PAPOYAN, S. +

  DOI：——

  日期：——
• Carboxamidation of carboxylic acids with 1-tert-butoxy-2-tert-butoxycarbonyl-1,2-dihydroisoquinoline (BBDI) without bases
  作者：Yukako Saito、Hidekazu Ouchi、Hiroki Takahata

  DOI：10.1016/j.tet.2008.09.094

  日期：2008.12

  Formation of carboxamides of a variety of carboxylic acids with the coupling reagent BBDI is described, This procedure permits a one pot and simple operation without the need of any bases and no base was required for even use of amine hydrochlorides. In addition, an approach to BBDI-catalyzed carboxamidation is examined. (C) 2008 Elsevier Ltd. All rights reserved.
• Efficient peptide coupling method of conjugated carboxylic acids with methyl ester amino acids hydrochloride. Application to the synthesis of Fa-Met, an important enzymatic substrate
  作者：Jean Michel Brunel、Chanaz Salmi、Yves Letourneux

  DOI：10.1016/j.tetlet.2004.11.082

  日期：2005.1

  Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate reagent (BOP) serves as an efficient and versatile coupling reagent for the coupling Of Conjugated carboxylic acid with methyl ester amino acids hydrochloride allowing the synthesis of various Substituted amino acid derivatives in high chemical yields of up to 90%. The usefulness of this method is illustrated in the synthesis of Fa-Met, an important enzymatic substrate. (C) 2004 Elsevier Ltd. All rights reserved.