(S)-1-(benzo[b]thien-2-ylmethyl)-5-oxopyrrolidine-2-carboxylic acid | 181580-95-0

• 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: (S)-1-(benzo[b]thien-2-ylmethyl)-5-oxopyrrolidine-2-carboxylic acid
• 英文别名: (2S)-1-(1-benzothiophen-2-ylmethyl)-5-oxopyrrolidine-2-carboxylic acid
• CAS: 181580-95-0
• 化学式: C₁₄H₁₃NO₃S
• 分子量: 275.328
• InChiKey: HNVAQEPEZOOCLK-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-(benzo[b]thien-2-ylmethyl)-5-oxopyrrolidine-2-carboxylic acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Highly diastereoselective approach to novel phenylindolizidinols via benzothieno analogues of tylophorine based on reductive desulfurization of benzo[b]thiophene

  摘要：

  Chiral tetra- and hexahydro[1]benzothieno[2,3-f]indolizines 3-5, 9, and 11 were synthesized easily from benzo[b]thiophene-2-carboxaldehyde (1) and (S)-glutamic acid (2) in good overall yields and both high enantio- and diastereomeric purities. Applying a diastereoselective reductive desulfurization of benzo[b]thiophene followed by lactam reduction, epimeric alcohols 4a and 4b were readily converted into (7R or S,8aS)-phenylindolizidinols 6a,c. During these studies, the reduction of benzothienoindolizines 3-5, 9, 11, and 12, was investigated and the results obtained are also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.042
• 作为产物：
  描述：

  (S)-N-(1-benzo[b]thien-2-ylmethyl)glutamic acid 以 乙醇 为溶剂， 反应 8.0h， 以74%的产率得到(S)-1-(benzo[b]thien-2-ylmethyl)-5-oxopyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Highly diastereoselective approach to novel phenylindolizidinols via benzothieno analogues of tylophorine based on reductive desulfurization of benzo[b]thiophene

  摘要：

  Chiral tetra- and hexahydro[1]benzothieno[2,3-f]indolizines 3-5, 9, and 11 were synthesized easily from benzo[b]thiophene-2-carboxaldehyde (1) and (S)-glutamic acid (2) in good overall yields and both high enantio- and diastereomeric purities. Applying a diastereoselective reductive desulfurization of benzo[b]thiophene followed by lactam reduction, epimeric alcohols 4a and 4b were readily converted into (7R or S,8aS)-phenylindolizidinols 6a,c. During these studies, the reduction of benzothienoindolizines 3-5, 9, 11, and 12, was investigated and the results obtained are also discussed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.042

文献信息

• Highly diastereoselective approach to novel phenylindolizidinols via benzothieno analogues of tylophorine based on reductive desulfurization of benzo[b]thiophene
  作者：Peter Šafář、Jozefína Žúžiová、Štefan Marchalín、Eva Tóthová、Nadežda Prónayová、Ľubomír Švorc、Viktor Vrábel、Adam Daïch

  DOI：10.1016/j.tetasy.2009.02.042

  日期：2009.3

  Chiral tetra- and hexahydro[1]benzothieno[2,3-f]indolizines 3-5, 9, and 11 were synthesized easily from benzo[b]thiophene-2-carboxaldehyde (1) and (S)-glutamic acid (2) in good overall yields and both high enantio- and diastereomeric purities. Applying a diastereoselective reductive desulfurization of benzo[b]thiophene followed by lactam reduction, epimeric alcohols 4a and 4b were readily converted into (7R or S,8aS)-phenylindolizidinols 6a,c. During these studies, the reduction of benzothienoindolizines 3-5, 9, 11, and 12, was investigated and the results obtained are also discussed. (C) 2009 Elsevier Ltd. All rights reserved.