2-[(2-ethylsulfanylacetyl)(2-furan-2-ylethyl)amino]cyclohex-1-enecarboxylic acid ethyl ester | 851072-23-6

• 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)(2-furan-2-ylethyl)amino]cyclohex-1-enecarboxylic acid ethyl ester
• 英文别名: Ethyl 2-[(2-ethylsulfanylacetyl)-[2-(furan-2-yl)ethyl]amino]cyclohexene-1-carboxylate；ethyl 2-[(2-ethylsulfanylacetyl)-[2-(furan-2-yl)ethyl]amino]cyclohexene-1-carboxylate
• CAS: 851072-23-6
• 化学式: C₁₉H₂₇NO₄S
• 分子量: 365.494
• InChiKey: PEXDZSUBEWCNPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 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)(2-furan-2-ylethyl)amino]cyclohex-1-enecarboxylic acid ethyl ester 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 15.0h， 以95%的产率得到2-[(2-ethanesulfinylacetyl)(2-furan-2-ylethyl)amino]cyclohex-1-enecarboxylic acid ethyl ester
  参考文献：
  名称：

  面向高赤藓生物碱（+/-）-硒代嘧啶的aza-Wittig / pi-呋喃环化方法。

  摘要：

  [反应：见正文]开发了一种一锅法，以有效地制备含有束缚的呋喃环的六氢吲哚满酮。呋喃基叠氮化物与Bu 3 P的反应得到亚氨基磷烷，使其与1-甲基-（2-氧代环己基）乙酸反应，得到所需的六氢吲哚酮环系统。用三氟乙酸进一步处理，得到在生物碱（+/-）-硒代嘧啶中发现的四环内酰胺骨架。

  DOI：

  10.1021/ol0501323
• 作为产物：
  描述：

  2-(呋喃-2-基)乙基甲磺酸负离子 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 16.5h， 生成 2-[(2-ethylsulfanylacetyl)(2-furan-2-ylethyl)amino]cyclohex-1-enecarboxylic 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

• An Aza-Wittig/π-Furan Cyclization Approach Toward the Homoerythrina Alkaloid (±)-Selaginoidine
  作者：Michael P. Cassidy、Ayse Daut Özdemir、Albert Padwa

  DOI：10.1021/ol0501323

  日期：2005.3.1

  react with 1-methyl-(2-oxocyclohexyl)acetic acid to give the desired hexahydroindolinone ring system. Further treatment with trifluoroacetic acid afforded the tetracyclic lactam skeleton found in the alkaloid (+/-)-selaginoidine.

  [反应：见正文]开发了一种一锅法，以有效地制备含有束缚的呋喃环的六氢吲哚满酮。呋喃基叠氮化物与Bu 3 P的反应得到亚氨基磷烷，使其与1-甲基-（2-氧代环己基）乙酸反应，得到所需的六氢吲哚酮环系统。用三氟乙酸进一步处理，得到在生物碱（+/-）-硒代嘧啶中发现的四环内酰胺骨架。
• 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.