1-methyl-1,3,4,5-tetrahydro-1H-azepino[5,4,3-cd]indole | 606977-33-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 1-methyl-1,3,4,5-tetrahydro-1H-azepino[5,4,3-cd]indole
• 英文别名: 1-Methyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole hydrochloride；3-methyl-3,10-diazatricyclo[6.4.1.04,13]trideca-1,4,6,8(13)-tetraene
• CAS: 606977-33-7
• 化学式: C₁₂H₁₄N₂
• mdl: MFCD15732225
• 分子量: 186.257
• InChiKey: MDWVMEIPGBJOCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  17
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-1,3,4,5-tetrahydro-1H-azepino[5,4,3-cd]indole 在 氢氧化钾 、 肼 作用下， 以 乙二醇 、 邻二氯苯 、 异丙醇 为溶剂， 反应 23.5h， 生成 (3R,11R,19S)-12-methyl-1,10,12-triazahexacyclo[15.4.1.03,19.04,9.011,19.013,18]docosa-4,6,8,13,15,17-hexaene
  参考文献：
  名称：

  A Synthetic Approach to Nomofungin/Communesin B

  摘要：

  [GRAPHICS]A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an orthoquinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.

  DOI：

  10.1021/ol034407v
• 作为产物：
  描述：

  1-甲基-1H-吲哚-4-羧酸甲酯 在 platinum(IV) oxide lithium aluminium tetrahydride 、 对叔丁基邻苯二酚 、 氢气 作用下， 以 四氢呋喃 、 乙醇 、 xylene 为溶剂， 反应 102.0h， 生成 1-methyl-1,3,4,5-tetrahydro-1H-azepino[5,4,3-cd]indole
  参考文献：
  名称：

  A Synthetic Approach to Nomofungin/Communesin B

  摘要：

  [GRAPHICS]A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an orthoquinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.

  DOI：

  10.1021/ol034407v

文献信息

• A Synthetic Approach to Nomofungin/Communesin B
  作者：Seth L. Crawley、Raymond L. Funk

  DOI：10.1021/ol034407v

  日期：2003.9.1

  [GRAPHICS]A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an orthoquinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.