7-氯-3-甲基-1H-吲哚-1-羧酸叔丁酯 | 797031-78-8

• 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
• 中文名称: 7-氯-3-甲基-1H-吲哚-1-羧酸叔丁酯
• 英文名称: tert-butyl 7-chloro-3-methylindole-1-carboxylate
• 英文别名: Tert-butyl 7-chloro-3-methyl-1H-indole-1-carboxylate
• CAS: 797031-78-8
• 化学式: C₁₄H₁₆ClNO₂
• 分子量: 265.74
• InChiKey: IDXAMDBQZZCHTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-氯-3-甲基-1H-吲哚-1-羧酸叔丁酯 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 偶氮二异丁腈 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 96.83h， 生成 tert-butyl 7-chloro-3-(5R-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2S-ylmethyl)indole-1-carboxylate
  参考文献：
  名称：

  Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662

  摘要：

  The structure of the unusual anthelmintic pyrrolobenzoxazine terpenoid natural product CJ-12662 was established by X-ray crystallography and partial synthesis from 2-chloronitrobenzene. An unusual Meisenheimer-type rearrangement was used to provide the core pyrrolobenzoxazine heterocycle, and coupling of a tetracyclic pyrrolobenzoxazine lactone with the terpene alcohol was used to complete the synthesis of CJ-12662.

  DOI：

  10.1021/jo048711t
• 作为产物：
  描述：

  硝基氯苯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 13.0h， 生成 7-氯-3-甲基-1H-吲哚-1-羧酸叔丁酯
  参考文献：
  名称：

  Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662

  摘要：

  The structure of the unusual anthelmintic pyrrolobenzoxazine terpenoid natural product CJ-12662 was established by X-ray crystallography and partial synthesis from 2-chloronitrobenzene. An unusual Meisenheimer-type rearrangement was used to provide the core pyrrolobenzoxazine heterocycle, and coupling of a tetracyclic pyrrolobenzoxazine lactone with the terpene alcohol was used to complete the synthesis of CJ-12662.

  DOI：

  10.1021/jo048711t

文献信息

• Full Stereochemical Assignment and Synthesis of the Potent Anthelmintic Pyrrolobenzoxazine Natural Product CJ-12662
  作者：Charles Didier、Douglas J. Critcher、Nigel D. Walshe、Yasuhiro Kojima、Yuji Yamauchi、Anthony G. M. Barrett

  DOI：10.1021/jo048711t

  日期：2004.11.1

  The structure of the unusual anthelmintic pyrrolobenzoxazine terpenoid natural product CJ-12662 was established by X-ray crystallography and partial synthesis from 2-chloronitrobenzene. An unusual Meisenheimer-type rearrangement was used to provide the core pyrrolobenzoxazine heterocycle, and coupling of a tetracyclic pyrrolobenzoxazine lactone with the terpene alcohol was used to complete the synthesis of CJ-12662.