(2aS,3S,6aS,6bS)-3-[(1S)-1,2-dihydroxyethyl]hexahydro-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one | 882032-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2aS,3S,6aS,6bS)-3-[(1S)-1,2-dihydroxyethyl]hexahydro-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one
• CAS: 882032-61-3
• 化学式: C₉H₁₃NO₅
• 分子量: 215.206
• InChiKey: OZXILKNQLRTLAN-QYYLWSOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.73
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  79.23
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2aS,3S,6aS,6bS)-3-[(1S)-1,2-dihydroxyethyl]hexahydro-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one 、 甲基磺酰氯 在 吡啶 作用下， 反应 2.0h， 生成
  参考文献：
  名称：

  Stereoselective synthesis of a new trihydroxyindolizidine lactone

  摘要：

  A general approach to 1,6,7-trihydroxyindolizidin-8-carboxylates is illustrated through the synthesis of a 7-lactone in an enantiopure form in seven steps starting from (3S)-3-t-butyloxy-1-pyrroline N-oxide and the acetonide of (2E,4S)-4,5-dihydroxy-2-pentenoic acid derived from (S)-malic acid and mannitol, respectively. The process was completely stereoselective and allowed the total control of the relative and absolute configuration of the five contiguous stereocentres of the product. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.003
• 作为产物：
  描述：

  (S)-(+)-3-(2,2-二甲基-1,3-二氧戊环-4-基)-反式-丙酸乙酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 三氟乙酸 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 xylene 为溶剂， 反应 96.17h， 生成 (2aS,3S,6aS,6bS)-3-[(1S)-1,2-dihydroxyethyl]hexahydro-2H-1,4-dioxa-4a-azacyclopenta[cd]pentalen-2-one
  参考文献：
  名称：

  Stereoselective synthesis of a new trihydroxyindolizidine lactone

  摘要：

  A general approach to 1,6,7-trihydroxyindolizidin-8-carboxylates is illustrated through the synthesis of a 7-lactone in an enantiopure form in seven steps starting from (3S)-3-t-butyloxy-1-pyrroline N-oxide and the acetonide of (2E,4S)-4,5-dihydroxy-2-pentenoic acid derived from (S)-malic acid and mannitol, respectively. The process was completely stereoselective and allowed the total control of the relative and absolute configuration of the five contiguous stereocentres of the product. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.003

文献信息

• Stereoselective synthesis of a new trihydroxyindolizidine lactone
  作者：Federica Pisaneschi、Michela Piacenti、Franca M. Cordero、Alberto Brandi

  DOI：10.1016/j.tetasy.2005.12.003

  日期：2006.1

  A general approach to 1,6,7-trihydroxyindolizidin-8-carboxylates is illustrated through the synthesis of a 7-lactone in an enantiopure form in seven steps starting from (3S)-3-t-butyloxy-1-pyrroline N-oxide and the acetonide of (2E,4S)-4,5-dihydroxy-2-pentenoic acid derived from (S)-malic acid and mannitol, respectively. The process was completely stereoselective and allowed the total control of the relative and absolute configuration of the five contiguous stereocentres of the product. (c) 2005 Elsevier Ltd. All rights reserved.