Hexahydro-(3R*,3aS*,6aR*)-3a-(1,3-benzodioxol-5-yl)-3-(benzoyloxy)-1-(1'(S*)-phenylethyl)cyclopentapyrrole-2,5(1H)-dione, 5-(1,3-Propanediyl dithioketal) | 136631-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: Hexahydro-(3R*,3aS*,6aR*)-3a-(1,3-benzodioxol-5-yl)-3-(benzoyloxy)-1-(1'(S*)-phenylethyl)cyclopentapyrrole-2,5(1H)-dione, 5-(1,3-Propanediyl dithioketal)
• CAS: 136631-36-2
• 化学式: C₃₂H₃₃NO₄S₂
• 分子量: 559.75
• InChiKey: KQJQZXZHXWNFPJ-UYUUSHKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.57
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Hexahydro-(3R*,3aS*,6aR*)-3a-(1,3-benzodioxol-5-yl)-3-(benzoyloxy)-1-(1'(S*)-phenylethyl)cyclopentapyrrole-2,5(1H)-dione, 5-(1,3-Propanediyl dithioketal) 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 0.53h， 生成 Hexahydro-(3R*,3aS*,6aR*)-3a-(1,3-benzodioxol-5-yl)-3-(benzyloxy)-1-(1'(S*)-phenylethyl)cyclopentapyrrole-2,5(1H)-dione
  参考文献：
  名称：

  Studies directed at the synthesis of optically active pretazettine via intramolecular nitrone/alkene cycloaddition reactions

  摘要：

  A protocol for the synthesis of optically active pretazettine which focuses on both the control of relative stereochemistry between the angular aryl and C6a hydroxyl groups and absolute stereochemistry has been developed and executed. The synthesis of the 1,3-dithiane ketal of (Z)-ethyl 3-(1,3-benzodioxol-5-yl)-5,7-dioxo-2-heptanoate is described. Treatment of this alkene aldehyde with N-(alpha-methylbenzyl)hydroxylamine afforded a nitrone, which underwent intramolecular 1,3-dipolar cycloaddition to afford the two diastereomeric isoxazolidine cycloadducts in a 16:1 ratio. The sense of chirality transfer was determined by a single-crystal X-ray analysis of the major isomer.

  DOI：

  10.1021/jo00023a019
• 作为产物：
  描述：

  2-(2,2-dimethoxyethyl)1,3-dithiane 在 盐酸 、 manganese(IV) oxide 、 正丁基锂 、 sodium hydride 、 potassium carbonate 、 二环己胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 81.5h， 生成 Hexahydro-(3R*,3aS*,6aR*)-3a-(1,3-benzodioxol-5-yl)-3-(benzoyloxy)-1-(1'(S*)-phenylethyl)cyclopentapyrrole-2,5(1H)-dione, 5-(1,3-Propanediyl dithioketal)
  参考文献：
  名称：

  Studies directed at the synthesis of optically active pretazettine via intramolecular nitrone/alkene cycloaddition reactions

  摘要：

  A protocol for the synthesis of optically active pretazettine which focuses on both the control of relative stereochemistry between the angular aryl and C6a hydroxyl groups and absolute stereochemistry has been developed and executed. The synthesis of the 1,3-dithiane ketal of (Z)-ethyl 3-(1,3-benzodioxol-5-yl)-5,7-dioxo-2-heptanoate is described. Treatment of this alkene aldehyde with N-(alpha-methylbenzyl)hydroxylamine afforded a nitrone, which underwent intramolecular 1,3-dipolar cycloaddition to afford the two diastereomeric isoxazolidine cycloadducts in a 16:1 ratio. The sense of chirality transfer was determined by a single-crystal X-ray analysis of the major isomer.

  DOI：

  10.1021/jo00023a019