caulersin

• 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: caulersin
• 英文别名: Methyl 2-oxo-10,21-diazapentacyclo[12.7.0.03,11.04,9.015,20]henicosa-1(14),3(11),4,6,8,12,15,17,19-nonaene-12-carboxylate
• 化学式: C₂₁H₁₄N₂O₃
• 分子量: 342.354
• InChiKey: RLYAECUXPZNGJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  75
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1H-吲哚-2-羰酰氯 在 水 、 二甲基氯化铝 作用下， 以 正己烷 、 二氯甲烷 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 36.75h， 生成 caulersin
  参考文献：
  名称：

  Synthesis of the marine alkaloid caulersin

  摘要：

  A three-step synthesis of caulersin (3) from indole-2-acetic acid methyl ester and indole-2-carbonyl chloride is described. As the spectral data of the synthetic sample differed from those reported for the natural product, the structure was determined by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.046

文献信息

• Synthesis of caulersin and its isomers by reaction of indole-2,3-dicarboxylic anhydrides with methyl indoleacetates
  作者：Yasuyoshi Miki、Yosiyuki Aoki、Hideaki Miyatake、Toshie Minematsu、Hajime Hibino

  DOI：10.1016/j.tetlet.2006.04.157

  日期：2006.7

  1-Benzenesulfonylindole-2,3-dicarboxylic anhydride was reacted with methyl 1-benzenesulfonylindole-2-acetate to give the corresponding 2-acylindole-3-carboxylic acid as the sole product in high yield, which could be converted to caulersin in four steps. In a similar manner, three isomers A, B, and C were synthesized by reaction of indole-2,3-dicarboxylic anhydrides with methyl indoleacetates.

  使1-苯磺酰基吲哚-2，3-二羧酸酐与1-苯磺酰基吲哚-2-乙酸甲酯反应，以高收率得到相应的2-酰基吲哚-3-羧酸为唯一产物，该产物可通过四步转化为花椰菜素。以类似的方式，通过吲哚-2，3-二羧酸酐与吲哚乙酸甲酯的反应合成了三种异构体A，B和C。
• The First Synthesis of the Bis(indole) Marine Alkaloid Caulersin
  作者：Pilar M. Fresneda、Pedro Molina、María Angeles Saez

  DOI：10.1055/s-1999-2903

  日期：——

  The first synthesis (seven steps) of the bis(indole) marine alkaloid caulersin is described. Construction of the central seven-membered ring is based on a Michael-type addition of the appropriate 2,3′-bis(indolyl)ketone to methylvinylketone followed by intramolecular nucleophilic substitution of the resulting 3-oxoalkylated product.

  描述了双（吲哚）海洋生物碱考勒素的第一次合成（七个步骤）。中心七元环的构建基于适当的 2,3'-双（吲哚基）酮与甲基乙烯基酮的迈克尔型加成，然后对所得 3-氧代烷基化产物进行分子内亲核取代。
• Synthesis of the marine alkaloid caulersin
  作者：Niklas Wahlström、Birgitta Stensland、Jan Bergman

  DOI：10.1016/j.tet.2003.12.046

  日期：2004.2

  A three-step synthesis of caulersin (3) from indole-2-acetic acid methyl ester and indole-2-carbonyl chloride is described. As the spectral data of the synthetic sample differed from those reported for the natural product, the structure was determined by X-ray crystallography. (C) 2004 Elsevier Ltd. All rights reserved.