1-<(2,3,4,5-tetrahydro-2-thienyl)acetyl>-1H-indole | 219532-40-8

• 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
• 英文名称: 1-<(2,3,4,5-tetrahydro-2-thienyl)acetyl>-1H-indole
• 英文别名: 1-Indol-1-yl-2-(thiolan-2-yl)ethanone
• CAS: 219532-40-8
• 化学式: C₁₄H₁₅NOS
• 分子量: 245.345
• InChiKey: CTBKADXIMBVQPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<(2,3,4,5-tetrahydro-2-thienyl)acetyl>-1H-indole 在 sodium periodate 作用下， 以 水 、 丙酮 为溶剂， 反应 26.0h， 以85%的产率得到1-<(2,3,4,5-tetrahydro-2-thienyl)acetyl>-1H-indole S-oxide
  参考文献：
  名称：

  A Sulfoxide-Based Ring Annelation Approach to Fused, Many-Membered Ring N,S-Heterocycles¹

  摘要：

  An approach to many-membered ring N,S-heterocycles involving sulfoxide electrophilic sulfenylation (SES followed by ring expansion of the derived sulfonium salt intermediate tin situ) is illustrated for 9- and 10-membered-ring compounds. Treatment of readily prepared sulfoxides 10a, 10b, 18a, 18b, 23a, and 23b with triflic anhydride (pyridine, CH2Cl2, 0 degrees C) provides heterocycles 13a (65%), 13b (60%), 19a (67%), 19b (67%), 24a (42%), and 24b (80%), respectively. Sulfoxides 5a and 5b, under several different conditions, give only the Pummerer dehydration products 6a and 6b, respectively. Diastereomeric sulfoxides 18a' and 18b', upon treatment with triflic anhydride, do not produce clean product mixtures or any of the desired heterocyclic products but, upon heating in toluene, are converted to the more stable isomers 18a and 18b, respectively. Conducting this isomerization in the presence of 2-mercaptobenzothiazole produces a disulfide indicative of the intermediacy of a sulfenic acid. However, the importance of sulfenic acid derivatives in the SES process leading to many-membered ring heterocycles remains to be determined.

  DOI：

  10.1021/jo9805044
• 作为产物：
  描述：

  2,3,4,5-tetrahydrothiophene-2-acetic acid 在 sodium hydroxide 、 草酰氯 、 四丁基硫酸氢铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 1-<(2,3,4,5-tetrahydro-2-thienyl)acetyl>-1H-indole
  参考文献：
  名称：

  A Sulfoxide-Based Ring Annelation Approach to Fused, Many-Membered Ring N,S-Heterocycles¹

  摘要：

  An approach to many-membered ring N,S-heterocycles involving sulfoxide electrophilic sulfenylation (SES followed by ring expansion of the derived sulfonium salt intermediate tin situ) is illustrated for 9- and 10-membered-ring compounds. Treatment of readily prepared sulfoxides 10a, 10b, 18a, 18b, 23a, and 23b with triflic anhydride (pyridine, CH2Cl2, 0 degrees C) provides heterocycles 13a (65%), 13b (60%), 19a (67%), 19b (67%), 24a (42%), and 24b (80%), respectively. Sulfoxides 5a and 5b, under several different conditions, give only the Pummerer dehydration products 6a and 6b, respectively. Diastereomeric sulfoxides 18a' and 18b', upon treatment with triflic anhydride, do not produce clean product mixtures or any of the desired heterocyclic products but, upon heating in toluene, are converted to the more stable isomers 18a and 18b, respectively. Conducting this isomerization in the presence of 2-mercaptobenzothiazole produces a disulfide indicative of the intermediacy of a sulfenic acid. However, the importance of sulfenic acid derivatives in the SES process leading to many-membered ring heterocycles remains to be determined.

  DOI：

  10.1021/jo9805044

文献信息

• A Sulfoxide-Based Ring Annelation Approach to Fused, Many-Membered Ring <b><i>N</i></b>,<b><i>S</i></b>-Heterocycles¹
  作者：Dallas K. Bates、Mingde Xia

  DOI：10.1021/jo9805044

  日期：1998.12.1

  An approach to many-membered ring N,S-heterocycles involving sulfoxide electrophilic sulfenylation (SES followed by ring expansion of the derived sulfonium salt intermediate tin situ) is illustrated for 9- and 10-membered-ring compounds. Treatment of readily prepared sulfoxides 10a, 10b, 18a, 18b, 23a, and 23b with triflic anhydride (pyridine, CH2Cl2, 0 degrees C) provides heterocycles 13a (65%), 13b (60%), 19a (67%), 19b (67%), 24a (42%), and 24b (80%), respectively. Sulfoxides 5a and 5b, under several different conditions, give only the Pummerer dehydration products 6a and 6b, respectively. Diastereomeric sulfoxides 18a' and 18b', upon treatment with triflic anhydride, do not produce clean product mixtures or any of the desired heterocyclic products but, upon heating in toluene, are converted to the more stable isomers 18a and 18b, respectively. Conducting this isomerization in the presence of 2-mercaptobenzothiazole produces a disulfide indicative of the intermediacy of a sulfenic acid. However, the importance of sulfenic acid derivatives in the SES process leading to many-membered ring heterocycles remains to be determined.