2-[(2-ethylsulfanylacetyl)-(3-furan-2-yl-propyl)amino]-cyclohex-1-ene-carboxylic acid ethyl ester | 925688-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-[(2-ethylsulfanylacetyl)-(3-furan-2-yl-propyl)amino]-cyclohex-1-ene-carboxylic acid ethyl ester
• 英文别名: Ethyl 2-[(2-ethylsulfanylacetyl)-[3-(furan-2-yl)propyl]amino]cyclohexene-1-carboxylate
• CAS: 925688-28-4
• 化学式: C₂₀H₂₉NO₄S
• 分子量: 379.521
• InChiKey: KQBNSELLYWHGDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2-ethylsulfanylacetyl)-(3-furan-2-yl-propyl)amino]-cyclohex-1-ene-carboxylic acid ethyl ester 在 sodium periodate 、 D(+)-10-樟脑磺酸 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 15.5h， 生成 3-ethylsulfanyl-1-(3-furan-2-ylpropyl)-2-oxo-1,2,3,4,5,6-hexahydroindole-3a-carboxylic acid ethyl ester
  参考文献：
  名称：

  Acid-Promoted Cyclization Reactions of Tetrahydroindolinones. Model Studies for Possible Application in a Synthesis of Selaginoidine

  摘要：

  [GRAPHIC]The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare tetrahydroindolinones containing tethered furan rings. In a typical example, the reaction of furanyl azide 26 with n-Bu3P delivered iminophosphorane 27, which was allowed to react with a 1-alkyl-(2-oxocyclohexyl)acetic acid to provide the desired furanyl-substituted tetrahydroindolinone system 29. Treatment of 29 with trifluoroacetic acid afforded the tetracyclic lactam skeleton 30 found in the alkaloid (+/-)-selaginoidine.

  DOI：

  10.1021/jo0619783
• 作为产物：
  描述：

  3-(2-呋喃基)丙烷-1-草酸铵 、 2-(ethylthio)acetyl chloride 、 2-环己酮甲酸乙酯 在 4 A molecular sieve 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以46%的产率得到2-[(2-ethylsulfanylacetyl)-(3-furan-2-yl-propyl)amino]-cyclohex-1-ene-carboxylic acid ethyl ester
  参考文献：
  名称：

  Acid-Promoted Cyclization Reactions of Tetrahydroindolinones. Model Studies for Possible Application in a Synthesis of Selaginoidine

  摘要：

  [GRAPHIC]The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare tetrahydroindolinones containing tethered furan rings. In a typical example, the reaction of furanyl azide 26 with n-Bu3P delivered iminophosphorane 27, which was allowed to react with a 1-alkyl-(2-oxocyclohexyl)acetic acid to provide the desired furanyl-substituted tetrahydroindolinone system 29. Treatment of 29 with trifluoroacetic acid afforded the tetracyclic lactam skeleton 30 found in the alkaloid (+/-)-selaginoidine.

  DOI：

  10.1021/jo0619783

文献信息

• Acid-Promoted Cyclization Reactions of Tetrahydroindolinones. Model Studies for Possible Application in a Synthesis of Selaginoidine
  作者：Mickea D. Rose、Michael P. Cassidy、Paitoon Rashatasakhon、Albert Padwa

  DOI：10.1021/jo0619783

  日期：2007.1.1

  [GRAPHIC]The synthesis of various substituted bicyclic lactams by an acid-induced Pictet-Spengler reaction of tetrahydroindolinones bearing tethered heteroaromatic rings is presented. The outcome of the cyclization depends on the position of the furan tether, tether length, nature of the tethered heteroaromatic ring, and the substituent group present on the 5-position of the tethered heteroaryl group. A one-pot procedure was developed to efficiently prepare tetrahydroindolinones containing tethered furan rings. In a typical example, the reaction of furanyl azide 26 with n-Bu3P delivered iminophosphorane 27, which was allowed to react with a 1-alkyl-(2-oxocyclohexyl)acetic acid to provide the desired furanyl-substituted tetrahydroindolinone system 29. Treatment of 29 with trifluoroacetic acid afforded the tetracyclic lactam skeleton 30 found in the alkaloid (+/-)-selaginoidine.