(R)-5-[2-(5-Carboxy-thiophen-2-yl)-ethyl]-2-oxo-piperidine-3-carboxylic acid ethyl ester | 187849-13-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-5-[2-(5-Carboxy-thiophen-2-yl)-ethyl]-2-oxo-piperidine-3-carboxylic acid ethyl ester
• 英文别名: 5-[2-[(3R)-5-ethoxycarbonyl-6-oxopiperidin-3-yl]ethyl]thiophene-2-carboxylic acid
• CAS: 187849-13-4
• 化学式: C₁₅H₁₉NO₅S
• 分子量: 325.386
• InChiKey: PQHJRSZJITUORO-BFHBGLAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-5-[2-(5-Carboxy-thiophen-2-yl)-ethyl]-2-oxo-piperidine-3-carboxylic acid ethyl ester 在 tetraphosphorus decasulfide 作用下， 以 四氢呋喃 为溶剂， 生成 5-[2-((R)-2-Amino-4-oxo-3,4,5,6,7,8-hexahydro-pyrido[2,3-d]pyrimidin-6-yl)-ethyl]-thiophene-2-carboxylic acid
  参考文献：
  名称：

  Asymmetric synthesis of dideazafolate antitumor agents via amidomethylation of nonracemic oxazolidinone imidates. Synthesis of LY309887, a cytotoxic dideazafolate analog related to lometrexol

  摘要：

  The asymmetric synthesis of LY309887, a cytotoxic dideazatetrahydrofolate analog related to lometrexol, has been accomplished via an application of diastereoselective amidomethylation of a chiral titanium (TV) acyloxazolidinone enolate. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02418-5
• 作为产物：
  描述：

  benzyl 5-[(3S)-3-(hydroxymethyl)-4-(phenylmethoxycarbonylamino)butyl]thiophene-2-carboxylate 在 氢溴酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 (R)-5-[2-(5-Carboxy-thiophen-2-yl)-ethyl]-2-oxo-piperidine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Asymmetric synthesis of dideazafolate antitumor agents via amidomethylation of nonracemic oxazolidinone imidates. Synthesis of LY309887, a cytotoxic dideazafolate analog related to lometrexol

  摘要：

  The asymmetric synthesis of LY309887, a cytotoxic dideazatetrahydrofolate analog related to lometrexol, has been accomplished via an application of diastereoselective amidomethylation of a chiral titanium (TV) acyloxazolidinone enolate. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02418-5

文献信息

• Asymmetric synthesis of dideazafolate antitumor agents via amidomethylation of nonracemic oxazolidinone imidates. Synthesis of LY309887, a cytotoxic dideazafolate analog related to lometrexol
  作者：Charles J. Barnett、Thomas M. Wilson、David A. Evans、Todd C. Somers

  DOI：10.1016/s0040-4039(96)02418-5

  日期：1997.2

  The asymmetric synthesis of LY309887, a cytotoxic dideazatetrahydrofolate analog related to lometrexol, has been accomplished via an application of diastereoselective amidomethylation of a chiral titanium (TV) acyloxazolidinone enolate. (C) 1997, Elsevier Science Ltd.