2-(1-methoxy-1-methylethyl)-2,3-dihydrobenzo[b]thiophene-7-carboxylic acid | 532412-78-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(1-methoxy-1-methylethyl)-2,3-dihydrobenzo[b]thiophene-7-carboxylic acid
• 英文别名: 2-(2-Methoxypropan-2-yl)-2,3-dihydro-1-benzothiophene-7-carboxylic acid；2-(2-methoxypropan-2-yl)-2,3-dihydro-1-benzothiophene-7-carboxylic acid
• CAS: 532412-78-5
• 化学式: C₁₃H₁₆O₃S
• 分子量: 252.334
• InChiKey: LXJWFWKGFBDDPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 2-(1-methoxy-1-methylethyl)-2,3-dihydrobenzo[b]thiophene-7-carboxylic acid 生成 2-(1-methoxy-1-methylethyl)-2,3-dihydrobenzo[b]thiophene-7-carboxylic acid methyl ester
  参考文献：
  名称：

  Small Molecules That Mimic the Thiol-Triggered Alkylating Properties Seen in the Natural Product Leinamycin

  摘要：

  Reaction of the antitumor agent leinamycin with cellular thiols results in conversion of the natural product to a DNA-alkylating episulfonium alkylating agent via an intriguing sequence of chemical reactions. To establish whether the chemistry first seen in leinamycin represents a general motif that can function in various molecular frameworks, construction of greatly simplified analogues containing only the "core" funcional groups anticipated to be necessary for thiol-triggered generation of an alkylating agent was undertaken. For this purpose, the "stripped-down" leinamycin analogue 7-(3-methyl-but-2-enyl)-1-oxo-1H-lambda4-benzo[1,2]dithiol-3-one (4) was synthesized. Treatment of 4 with thiol under several different conditions results in efficient conversion of the compound to cyclized 2,3-dihydro-benzo[b]thiophene-7-carboxylic acid products (13) that are envisioned to arise from Markovnikov addition of solvent to an intermediate episulfonium ion (14). Thus, the relatively simple molecule 4 is able to mimic the thiol-triggered alkylating properties displayed by the natural product leinamycin. This work helps define why the core functional groups required thiol-accelerated generation of an alkylating intermediate from leinamycin and indicates that substantially altered analogues of the natural product may retain alkylating properties. In a broader context, the results provide evidence that the unique cascade of chemical reactions first seen in the context of leinamycin represents a general motif that can operate in a variety of molecular frameworks.

  DOI：

  10.1021/ja029169y
• 作为产物：
  描述：

  7-(3-methylbut-2-enyl)benzo[1,2]dithiol-3-one 在 丙烷-1-硫醇 、 sodium phosphate buffer 、 二甲基二环氧乙烷 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 1.5h， 生成 2-(1-methoxy-1-methylethyl)-2,3-dihydrobenzo[b]thiophene-7-carboxylic acid
  参考文献：
  名称：

  Small Molecules That Mimic the Thiol-Triggered Alkylating Properties Seen in the Natural Product Leinamycin

  摘要：

  Reaction of the antitumor agent leinamycin with cellular thiols results in conversion of the natural product to a DNA-alkylating episulfonium alkylating agent via an intriguing sequence of chemical reactions. To establish whether the chemistry first seen in leinamycin represents a general motif that can function in various molecular frameworks, construction of greatly simplified analogues containing only the "core" funcional groups anticipated to be necessary for thiol-triggered generation of an alkylating agent was undertaken. For this purpose, the "stripped-down" leinamycin analogue 7-(3-methyl-but-2-enyl)-1-oxo-1H-lambda4-benzo[1,2]dithiol-3-one (4) was synthesized. Treatment of 4 with thiol under several different conditions results in efficient conversion of the compound to cyclized 2,3-dihydro-benzo[b]thiophene-7-carboxylic acid products (13) that are envisioned to arise from Markovnikov addition of solvent to an intermediate episulfonium ion (14). Thus, the relatively simple molecule 4 is able to mimic the thiol-triggered alkylating properties displayed by the natural product leinamycin. This work helps define why the core functional groups required thiol-accelerated generation of an alkylating intermediate from leinamycin and indicates that substantially altered analogues of the natural product may retain alkylating properties. In a broader context, the results provide evidence that the unique cascade of chemical reactions first seen in the context of leinamycin represents a general motif that can operate in a variety of molecular frameworks.

  DOI：

  10.1021/ja029169y

文献信息

• Small Molecules That Mimic the Thiol-Triggered Alkylating Properties Seen in the Natural Product Leinamycin
  作者：Tonika Chatterji、Murat Kizil、Kripa Keerthi、Goutam Chowdhury、Tomás Pospísil、Kent S. Gates

  DOI：10.1021/ja029169y

  日期：2003.4.1

  Reaction of the antitumor agent leinamycin with cellular thiols results in conversion of the natural product to a DNA-alkylating episulfonium alkylating agent via an intriguing sequence of chemical reactions. To establish whether the chemistry first seen in leinamycin represents a general motif that can function in various molecular frameworks, construction of greatly simplified analogues containing only the "core" funcional groups anticipated to be necessary for thiol-triggered generation of an alkylating agent was undertaken. For this purpose, the "stripped-down" leinamycin analogue 7-(3-methyl-but-2-enyl)-1-oxo-1H-lambda4-benzo[1,2]dithiol-3-one (4) was synthesized. Treatment of 4 with thiol under several different conditions results in efficient conversion of the compound to cyclized 2,3-dihydro-benzo[b]thiophene-7-carboxylic acid products (13) that are envisioned to arise from Markovnikov addition of solvent to an intermediate episulfonium ion (14). Thus, the relatively simple molecule 4 is able to mimic the thiol-triggered alkylating properties displayed by the natural product leinamycin. This work helps define why the core functional groups required thiol-accelerated generation of an alkylating intermediate from leinamycin and indicates that substantially altered analogues of the natural product may retain alkylating properties. In a broader context, the results provide evidence that the unique cascade of chemical reactions first seen in the context of leinamycin represents a general motif that can operate in a variety of molecular frameworks.