(3aS,4S,5R,7aR)-octahydro-4,5-O-isopropylidenedioxy-3a-(3,4-methylenedioxy)phenylindole | 172330-39-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (3aS,4S,5R,7aR)-octahydro-4,5-O-isopropylidenedioxy-3a-(3,4-methylenedioxy)phenylindole
• 英文别名: (3aR,5aR,8aS,8bS)-8a-(1,3-benzodioxol-5-yl)-2,2-dimethyl-3a,4,5,5a,6,7,8,8b-octahydro-[1,3]dioxolo[4,5-e]indole
• CAS: 172330-39-1
• 化学式: C₁₈H₂₃NO₄
• 分子量: 317.385
• InChiKey: MSNZSNKZZZBNJV-IIVZCXTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4S,5R,7aR)-octahydro-4,5-O-isopropylidenedioxy-3a-(3,4-methylenedioxy)phenylindole 在 盐酸 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (-)-amabiline
  参考文献：
  名称：

  Short, Efficient Syntheses of the Amaryllidaceae Alkaloids (-)-Amabiline and (-)-Augustamine via Intramolecular 2-Azaallyl Anion Cycloadditions

  摘要：

  DOI：

  10.1021/ja00154a037
• 作为产物：
  描述：

  3,4-methylenedioxyphenyllithium 在 吡啶 、 正丁基锂 、 4 A molecular sieve 、 水 作用下， 生成 (3aS,4S,5R,7aR)-octahydro-4,5-O-isopropylidenedioxy-3a-(3,4-methylenedioxy)phenylindole
  参考文献：
  名称：

  Short, Efficient Syntheses of the Amaryllidaceae Alkaloids (-)-Amabiline and (-)-Augustamine via Intramolecular 2-Azaallyl Anion Cycloadditions

  摘要：

  DOI：

  10.1021/ja00154a037

文献信息

• Assembly of 3a-Arylperhydroindoles by the Intramolecular Cycloaddition of 2-Azaallyl Anions with Alkenes. Total Syntheses of (±)-Crinine, (±)-6-Epicrinine, (−)-Amabiline, and (−)-Augustamine
  作者：William H. Pearson、Frank E. Lovering

  DOI：10.1021/jo972255+

  日期：1998.5.1

  The 2-azaallyl anion route to pyrrolidines was used for the concise synthesis of alkaloids featuring the 3a-arylperhydroindole nucleus. The brevity and efficiency of the syntheses described are particularly notable. The key transformations involved the tin-lithium exchange of (2-azaallyl)stannanes to 2-azaallyl anions, which participated in intramolecular [pi 4s + pi 2s] cycloadditions with styrenes to produce the requisite 3a-arylperhydroindoles. (+/-)-Crinine was synthesized in eight steps in 20% overall yield, with the key cycloaddition producing a single stereoisomer of the perhydroindole in 80% yield. (+/-)-6-Epicrinine was an intermediate in this synthesis. The key cycloaddition involved the use of a diene as the anionophile. The first asymmetric syntheses of (-)-amabiline and (-)-augustamine were accomplished in overall yields of 43% (in eight steps) and 42% (in nine steps), respectively, confirming or determining the absolute stereochemistry of the natural products. The key cycloadditions produced the perhydroindoles in 83% and 74% yields, respectively, with reasonable stereocontrol. The highly stereoselective cycloaddition leading to a trans-dialkoxyperhydroindole in 75% yield was consistent with stereochemical predictions. These studies contribute to a growing body of knowledge on the scope and stereochemistry of 2-azaallyl anion cycloadditions.
• Short, Efficient Syntheses of the Amaryllidaceae Alkaloids (-)-Amabiline and (-)-Augustamine via Intramolecular 2-Azaallyl Anion Cycloadditions
  作者：William H. Pearson、Frank E. Lovering

  DOI：10.1021/ja00154a037

  日期：1995.12