1-phenyl-8a-hydroxy-2-oxo-1,2,6,7,8,8a-hexahydrobenzo[cd]indole-3-carboxylic acid | 922508-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-phenyl-8a-hydroxy-2-oxo-1,2,6,7,8,8a-hexahydrobenzo[cd]indole-3-carboxylic acid
• 英文别名: 8a-hydroxy-2-oxo-1-phenyl-7,8-dihydro-6H-benzo[cd]indole-3-carboxylic acid
• CAS: 922508-46-1
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: UCXWFNHFTDRULH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-phenyl-8a-hydroxy-2-oxo-1,2,6,7,8,8a-hexahydrobenzo[cd]indole-3-carboxylic acid 在 盐酸 作用下， 以 氯仿 为溶剂， 反应 16.0h， 生成 1-phenyl-2-oxo-1,2,6,7-tetrahydrobenzo[cd]indole-3-carboxylic acid
  参考文献：
  名称：

  Unexpected regiospecific reactivity of a substituted phthalic anhydride

  摘要：

  Regioselective nucleophilic addition at C1 of anhydride 7 by a range of nucleophiles occurs to produce amide, ester and thioester derivatives 8-15 (60-99%). The increased electrophilic reactivity of the C I carbonyl group of anhydride 7 is supported by a competition experiment with phthalic anhydride. Unexpected formation of lactams 18 and 19 from amides 12 and 13 was shown to proceed via the lactamols 16 and 17 and could be controlled by the reaction conditions. The solid-state structure of 19 is reported. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.090
• 作为产物：
  描述：

  7,8-dihydro-6H-naphtho[1,2-c]furan-1,3,9-trione 以 氯仿 、 丙酮 为溶剂， 反应 48.25h， 生成 1-phenyl-8a-hydroxy-2-oxo-1,2,6,7,8,8a-hexahydrobenzo[cd]indole-3-carboxylic acid
  参考文献：
  名称：

  Unexpected regiospecific reactivity of a substituted phthalic anhydride

  摘要：

  Regioselective nucleophilic addition at C1 of anhydride 7 by a range of nucleophiles occurs to produce amide, ester and thioester derivatives 8-15 (60-99%). The increased electrophilic reactivity of the C I carbonyl group of anhydride 7 is supported by a competition experiment with phthalic anhydride. Unexpected formation of lactams 18 and 19 from amides 12 and 13 was shown to proceed via the lactamols 16 and 17 and could be controlled by the reaction conditions. The solid-state structure of 19 is reported. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.11.090

文献信息

• Unexpected regiospecific reactivity of a substituted phthalic anhydride
  作者：Maria J. Petersson、Camille Marchal、Wendy A. Loughlin、Ian D. Jenkins、Peter C. Healy、Ann Almesåker

  DOI：10.1016/j.tet.2006.11.090

  日期：2007.2

  Regioselective nucleophilic addition at C1 of anhydride 7 by a range of nucleophiles occurs to produce amide, ester and thioester derivatives 8-15 (60-99%). The increased electrophilic reactivity of the C I carbonyl group of anhydride 7 is supported by a competition experiment with phthalic anhydride. Unexpected formation of lactams 18 and 19 from amides 12 and 13 was shown to proceed via the lactamols 16 and 17 and could be controlled by the reaction conditions. The solid-state structure of 19 is reported. (c) 2006 Published by Elsevier Ltd.