3-(1-chloromethyl-6-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid ethyl ester | 591752-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(1-chloromethyl-6-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid ethyl ester
• 英文别名: ethyl 2-[1-(chloromethyl)-6-methyl-4,9-dihydro-3H-pyrano[3,4-b]indol-1-yl]acetate
• CAS: 591752-39-5
• 化学式: C₁₇H₂₀ClNO₃
• 分子量: 321.804
• InChiKey: OJTTYJSSAARGMD-UHFFFAOYSA-N

物化性质

• 沸点：
  478.5±40.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(1-chloromethyl-6-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid ethyl ester 在 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以42.5%的产率得到4-[3-(2-Hydroxy-ethyl)-5-methyl-1H-indol-2-yl]-4-oxo-butyric acid ethyl ester
  参考文献：
  名称：

  Base-mediated hydrolytic cleavage with chain migration of 1-chloromethyl-tetrahydropyrano[3,4-b]indoles: an unusual pathway to 2-succinoyl tryptophols

  摘要：

  An unusual hydrolytic cleavage with 1,2-alkyl chain migration of 1-chloromethyl-tetrahydropyrano[3,4-b]indoles by heating with a limited amount of water and base in DMF is reported. A mechanism for the formation of 1,2-alkyl chain migration products, 2-succinoyl tryptophols, and the ring-expansion products, dihydro-oxepine fused indoles, is reported. No comparable 1,2-chain migration from a structurally related 1-chloromethyl-isochroman is observed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.105
• 作为产物：
  描述：

  4-甲基苯肼盐酸盐 在 三氟化硼乙醚 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 生成 3-(1-chloromethyl-6-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid ethyl ester
  参考文献：
  名称：

  A Novel Substitution Reaction of Tetrahydropyrano[3,4-b]indole Derivative — Chain Extension and Structural Correlation Study

  摘要：

  An unusual cyanation with rearrangement of a 1-chloromethyltetrahydropyrano[3,4-b]indole-1-acetic acid ester derivative is reported. The resulting C-1 chain extension product is identified by correlation studies and spectral method.

  DOI：

  10.3987/com-02-9703

文献信息

• A Novel Substitution Reaction of Tetrahydropyrano[3,4-b]indole Derivative — Chain Extension and Structural Correlation Study
  作者：Shan-Yen Chou

  DOI：10.3987/com-02-9703

  日期：——

  An unusual cyanation with rearrangement of a 1-chloromethyltetrahydropyrano[3,4-b]indole-1-acetic acid ester derivative is reported. The resulting C-1 chain extension product is identified by correlation studies and spectral method.
• Base-mediated hydrolytic cleavage with chain migration of 1-chloromethyl-tetrahydropyrano[3,4-b]indoles: an unusual pathway to 2-succinoyl tryptophols
  作者：Shan-Yen Chou、Ching-Hui Chen

  DOI：10.1016/j.tetlet.2006.06.105

  日期：2006.8

  An unusual hydrolytic cleavage with 1,2-alkyl chain migration of 1-chloromethyl-tetrahydropyrano[3,4-b]indoles by heating with a limited amount of water and base in DMF is reported. A mechanism for the formation of 1,2-alkyl chain migration products, 2-succinoyl tryptophols, and the ring-expansion products, dihydro-oxepine fused indoles, is reported. No comparable 1,2-chain migration from a structurally related 1-chloromethyl-isochroman is observed. (c) 2006 Elsevier Ltd. All rights reserved.