(S)-N-(1-benzo[b]thien-3-ylmethyl)glutamic acid | 1199786-76-9

• 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)-N-(1-benzo[b]thien-3-ylmethyl)glutamic acid
• CAS: 1199786-76-9
• 化学式: C₁₄H₁₅NO₄S
• 分子量: 293.343
• InChiKey: DQNZPKUODIIYOU-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.63
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-benzo[b]thien-3-ylmethyl)glutamic acid 以 乙醇 为溶剂， 反应 8.0h， 以8.1 g的产率得到(S)-1-(benzo[b]thien-3-ylmethyl)-5-oxopyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and reductive desulfurization of chiral non-racemic benzothienoindolizines. An efficient approach to a novel bioactive tylophorine alkaloid analogue and 6-phenylindolizidine

  摘要：

  Enantiopure di- and tetrahydero[1]benzothieno[3.2-f]indolizines 3,4,9 and the benzothieno analogue 5 of the bioactive alkaloid tylophorine 10 were synthesized easily from the readily available benzo[b]thiophene-3-carboxaldehyde I and (S)-glutamic acid 2 in good over all yields. Applying a diastereoselective reductive desulfurization of benzo[b]thiophene 3.4 and 5 were readily converted into the enantiopure alcohols 11a-d, alcohols 11c,d and the target 6(R)-phenyl-8a(R)-indolizidine 6 (7 steps, 14%) During these reduction Studies. the results obtained including the sterieoinduction of the reaction are also discussed (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2009.08.010
• 作为产物：
  描述：

  3-甲醛苯并噻吩 、 L-谷氨酸 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 54.0h， 以80%的产率得到(S)-N-(1-benzo[b]thien-3-ylmethyl)glutamic acid
  参考文献：
  名称：

  Synthesis and reductive desulfurization of chiral non-racemic benzothienoindolizines. An efficient approach to a novel bioactive tylophorine alkaloid analogue and 6-phenylindolizidine

  摘要：

  Enantiopure di- and tetrahydero[1]benzothieno[3.2-f]indolizines 3,4,9 and the benzothieno analogue 5 of the bioactive alkaloid tylophorine 10 were synthesized easily from the readily available benzo[b]thiophene-3-carboxaldehyde I and (S)-glutamic acid 2 in good over all yields. Applying a diastereoselective reductive desulfurization of benzo[b]thiophene 3.4 and 5 were readily converted into the enantiopure alcohols 11a-d, alcohols 11c,d and the target 6(R)-phenyl-8a(R)-indolizidine 6 (7 steps, 14%) During these reduction Studies. the results obtained including the sterieoinduction of the reaction are also discussed (C) 2009 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.tetasy.2009.08.010