1-(Benzenesulfonyl)-3-(bromomethyl)-2-methylindole | 856112-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(Benzenesulfonyl)-3-(bromomethyl)-2-methylindole
• 英文别名: 1-(benzenesulfonyl)-3-(bromomethyl)-2-methylindole
• CAS: 856112-53-3
• 化学式: C₁₆H₁₄BrNO₂S
• 分子量: 364.263
• InChiKey: DITSUIYATBLGQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(Benzenesulfonyl)-3-(bromomethyl)-2-methylindole 在 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.83h， 生成
  参考文献：
  名称：

  Total Synthesis of Hapalindole-Type Natural Products

  摘要：

  AbstractA unified and bioinspired oxidative cyclization strategy was used in the first total syntheses of naturally occurring 12‐epi‐hapalindole Q isonitrile, hapalonamide H, deschloro 12‐epi‐fischerindole I nitrile, and deschloro 12‐epi‐fischerindole W nitrile, as well as the structural revision of the latter. Hapalindoles H and Q were also synthesized.

  DOI：

  10.1002/anie.201406626
• 作为产物：
  描述：

  1-(phenylsulfonyl)-2,3-dimethylindole 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 1-(Benzenesulfonyl)-3-(bromomethyl)-2-methylindole
  参考文献：
  名称：

  Stille carbonylation of N-protected bromomethylindoles

  摘要：

  A variety of N-protected indolylmethyl bromides are carbonylated using 5 mol % Pd(PPh3)(2)Cl-2 under Stille conditions in the presence of an alcohol to afford the corresponding methyl/ethyl esters. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.05.010

文献信息

• An efficient preparation of 1-phenylsulfonylindolyl methyl sulfoxides using KF/m-CPBA
  作者：Arasambattu K. Mohanakrishnan、Neelamegam Ramesh

  DOI：10.1016/j.tetlet.2005.04.067

  日期：2005.6

  A variety of 1-phenylsulfonylindolylmethyl sulfides are selectively oxidized to the corresponding sulfoxides using a hitherto unexplored KF/m-CPBA system. A major advantage is the absence of over-oxidation. (c) 2005 Elsevier Ltd. All rights reserved.
• Ramesh, Neelamegam; Dhayalan, Vasudevan; Sureshbabu, Radhakrishnan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 6, p. 858 - 864
  作者：Ramesh, Neelamegam、Dhayalan, Vasudevan、Sureshbabu, Radhakrishnan、Mohanakrishnan, Arasambattu K.

  DOI：——

  日期：——
• Total Synthesis of Hapalindole-Type Natural Products
  作者：Zhaohong Lu、Ming Yang、Pengxi Chen、Xiaochun Xiong、Ang Li

  DOI：10.1002/anie.201406626

  日期：2014.12.8

  AbstractA unified and bioinspired oxidative cyclization strategy was used in the first total syntheses of naturally occurring 12‐epi‐hapalindole Q isonitrile, hapalonamide H, deschloro 12‐epi‐fischerindole I nitrile, and deschloro 12‐epi‐fischerindole W nitrile, as well as the structural revision of the latter. Hapalindoles H and Q were also synthesized.
• Stille carbonylation of N-protected bromomethylindoles
  作者：Arasambattu K. Mohanakrishnan、Neelamegam Ramesh

  DOI：10.1016/j.tetlet.2005.05.010

  日期：2005.7

  A variety of N-protected indolylmethyl bromides are carbonylated using 5 mol % Pd(PPh3)(2)Cl-2 under Stille conditions in the presence of an alcohol to afford the corresponding methyl/ethyl esters. (c) 2005 Elsevier Ltd. All rights reserved.