(-)-(6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine | 126783-74-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (-)-(6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine
• 英文别名: (6R,7S,8R,8aS)-octahydroindolizine-6,7,8-triol；(6R,7S,8R,8aS)-6,7,8-Trihydroxyindolizidine；(6R,7S,8R,8aS)-Indolizidin-6,7,8-triol；1-deoxy-7,8a-di-epicastanospermine；(6R,7S,8R,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizine-6,7,8-triol
• CAS: 126783-74-2
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: NCQXPGNMJJWGLP-OSMVPFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (6R,7S,8R,8aS)-6,7,8-Triacetoxyindolizidin 在 甲醇 、 氨 作用下， 反应 15.0h， 以88%的产率得到(-)-(6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine
  参考文献：
  名称：

  Paulsen, Hans; Matzke, Michael; Orthen, Bruno, Liebigs Annalen der Chemie, 1990, # 10, p. 953 - 963

  摘要：

  DOI：

文献信息

• Synthesis of 1-deoxycastanospermine and stereoisomers
  作者：Yves St-Denis、Tak Hang Chan

  DOI：10.1021/jo00037a025

  日期：1992.5

  Four different isomers of 1-deoxycastanospermine (6,7,8-trihydroxyindolizidine) were synthesized. Their basic skeleton was constructed from a proline derivative and the anion of allyl phenyl sulfide, followed by an allylic sulfide rearrangement and a subsequent nucleophilic cyclization. The aminotriols were obtained in good yields with a concise overall sequence.
• Total synthesis of 1-deoxy-7,8a-di-epi-castanospermine and formal synthesis of pumiliotoxin-251D
  作者：Prakash R. Sultane、Amar R. Mohite、Ramakrishna G. Bhat

  DOI：10.1016/j.tetlet.2012.08.061

  日期：2012.10

  A concise and efficient synthesis of (6R,7S,8R,8aS)-6,7,8-trihydroxyindolizidine (1-deoxy-7,8a-di-epi-castanospermine) 2 is described. The synthesis employs cross metathesis in building the key intermediate 9 and is used effectively in constructing indolizidine skeleton for the total synthesis of 1-deoxy-7, 8a-di-epi-castanospermine and also for the bicyclic framework of pumiliotoxin 251D 12,13. The indolizidine skeleton is achieved in one pot sequence of transformations such as deprotection of Cbz group, reduction of double bond, and cyclization. The configurational and conformational structures of compound 10 are unambiguously confirmed by X-ray analysis. (C) 2012 Elsevier Ltd. All rights reserved.
• Casiraghi, Giovanni; Ulgheri, Fausta; Spanu, Pietro, Journal of the Chemical Society. Perkin transactions I, 1993, # 23, p. 2991 - 2998
  作者：Casiraghi, Giovanni、Ulgheri, Fausta、Spanu, Pietro、Rassu, Gloria、Pinna, Luigi、et al.

  DOI：——

  日期：——
• PAULSEN, HANS;MATZKE, MICHAEL;ORTHEN, BRUNO;NUCK, ROLF;REUTTER, WERNER, LIEBIGS ANN. CHEM.,(1990) N0, C. 953-963
  作者：PAULSEN, HANS、MATZKE, MICHAEL、ORTHEN, BRUNO、NUCK, ROLF、REUTTER, WERNER

  DOI：——

  日期：——