Methyl 2-(benzylamino)-3-phenylsulfanylpropanoate | 1011486-88-6

• 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: Methyl 2-(benzylamino)-3-phenylsulfanylpropanoate
• CAS: 1011486-88-6
• 化学式: C₁₇H₁₉NO₂S
• 分子量: 301.409
• InChiKey: PBAUAIHDYKZMLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((2-iodophenyl)(methyl)amino)-4-oxobut-2(E)-enoic acid 、 Methyl 2-(benzylamino)-3-phenylsulfanylpropanoate 在 N-甲基吗啉 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到
  参考文献：
  名称：

  A tandem radical cyclization approach to 3-(2-oxopyrrolidin-3-yl)indolin-2-ones, potential intermediates toward complex indole-heterocycles

  摘要：

  A series of substituted 3-(2-oxopyrrolidin-3-yl)indolin-2-one derivatives have been synthesized by tris(trimethylsilyl)silane (TTMSS) induced tandem radical cyclization as key step. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.194

文献信息

• Process for producing optically active cysteine derivatives
  申请人：Kaneka Corporation

  公开号：US20020169337A1

  公开（公告）日：2002-11-14

  A process for producing optically active cysteine derivatives with high optical purity and good quality which is economically advantageous and is high in productivity even on a commercial scale is provided. A process for producing an optically active cysteine derivative which comprises synthesizing a D-form or L-form optically active cysteine derivative of the general formula (2) shown below (R 1 represents an amino-protecting group of the urethane or acyl type, R 0 represents a hydrogen atom or, taken together with R 1 , an amino-protecting group, R 2 represents an alkyl, aryl or aralkyl group, R 3 represents a univalent organic group and * represents the position of an asymmetric carbon) by reacting the corresponding D-form or L-form optically active amino acid derivative of the general formula (1) shown below with an alcohol of the general formula (3) shown below and a strong acid and/or a thionyl halide and recovering the above cysteine derivative (2) from the reaction mixture, the procedural series from reaction to recovery being carried out under conditions such that the medium contacting the above optically active cysteine derivative (2) is within the range from acidic to weakly basic to thereby recover the above cysteine derivative (2) from the reaction mixture while suppressing the decomposition and racemization thereof. 1

  提供了一种生产高光学纯度和良好质量的光学活性半胱氨酸衍生物的工艺，该工艺在经济上具有优势，即使在商业规模上也具有高生产率。生产光学活性半胱氨酸衍生物的工艺包括通过将下面所示的一般式（1）的相应D型或L型光学活性氨基酸衍生物与下面所示的一般式（3）的醇和强酸和/或硫酰卤反应合成下面所示的一般式（2）的D型或L型光学活性半胱氨酸衍生物（其中R1表示脲或酰型氨基保护基，R0表示氢原子或与R1一起表示氨基保护基，R2表示烷基，芳基或芳基烷基，R3表示一价有机基团，*表示不对称碳的位置），并在其接触介质在酸性到微弱碱性范围内的条件下，从反应混合物中回收上述半胱氨酸衍生物（2），以抑制其分解和外消旋，从反应到回收的程序系列。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE CYSTEINE DERIVATIVES
  申请人：KANEKA CORPORATION

  公开号：EP1054000A1

  公开（公告）日：2000-11-22

  A process for producing optically active cysteine derivatives with high optical purity and good quality which is economically advantageous and is high in productivity even on a commercial scale is provided. A process for producing an optically active cysteine derivative which comprises synthesizing a D-form or L-form optically active cysteine derivative of the general formula (2) shown below (R1 represents an amino-protecting group of the urethane or acyl type, R0 represents a hydrogen atom or, taken together with R1, an amino-protecting group, R2 represents an alkyl, aryl or aralkyl group, R3 represents a univalent organic group and * represents the position of an asymmetric carbon) by reacting the corresponding D-form or L-form optically active amino acid derivative of the general formula (1) shown below with an alcohol of the general formula (3) shown below and a strong acid and/or a thionyl halide and recovering the above cysteine derivative (2) from the reaction mixture, the procedural series from reaction to recovery being carried out under conditions such that the medium contacting the above optically active cysteine derivative (2) is within the range from acidic to weakly basic to thereby recover the above cysteine derivative (2) from the reaction mixture while suppressing the decomposition and racemization thereof.

  本发明提供了一种生产光学纯度高、质量好的光学活性半胱氨酸衍生物的工艺，该工艺具有经济优势，即使在商业规模上也具有很高的生产率。 一种生产光学活性半胱氨酸衍生物的工艺，包括合成下图通式（2）的 D-型或 L-型光学活性半胱氨酸衍生物（R1 代表氨基保护基，属于氨基甲酸酯或酰基类型，R0 代表氢原子或与 R1 一起代表氨基保护基，R2 代表烷基、芳基或芳烷基、R3代表单价有机基团，*代表不对称碳的位置），将相应的下图所示通式（1）的 D-型或 L-型光学活性氨基酸衍生物与下图所示通式（3）的醇和强酸和/或硫代卤化物反应，并从反应混合物中回收上述半胱氨酸衍生物（2）、从反应到回收的一系列过程是在这样的条件下进行的：与上述具有光学活性的半胱氨酸衍生物（2）接触的介质处于从酸性到弱碱性的范围内，从而从反应混合物中回收上述半胱氨酸衍生物（2），同时抑制其分解和消旋化。
• US6407281B1
  申请人：——

  公开号：US6407281B1

  公开（公告）日：2002-06-18
• A tandem radical cyclization approach to 3-(2-oxopyrrolidin-3-yl)indolin-2-ones, potential intermediates toward complex indole-heterocycles
  作者：Marc Pudlo、Stéphane Gérard、Catherine Mirand、Janos Sapi

  DOI：10.1016/j.tetlet.2007.11.194

  日期：2008.2

  A series of substituted 3-(2-oxopyrrolidin-3-yl)indolin-2-one derivatives have been synthesized by tris(trimethylsilyl)silane (TTMSS) induced tandem radical cyclization as key step. (c) 2007 Elsevier Ltd. All rights reserved.