2-(ethylsulfanylmethyl)-N-[2-(1H-indol-3-yl)ethyl]benzamide | 202392-01-6

• 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: 2-(ethylsulfanylmethyl)-N-[2-(1H-indol-3-yl)ethyl]benzamide
• CAS: 202392-01-6
• 化学式: C₂₀H₂₂N₂OS
• 分子量: 338.473
• InChiKey: XSXIUBAGSIWAST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(ethylsulfanylmethyl)-N-[2-(1H-indol-3-yl)ethyl]benzamide 在 sodium hydroxide 、 sodium periodate 、 三氟甲磺酸三甲基硅酯 、 四丁基硫酸氢铵 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 25.08h， 生成 methyl 8-ethylsulfanyl-13-[2-[1-(4-methylphenyl)sulfonylindol-3-yl]ethyl]-12-oxo-14-oxa-13-azatetracyclo[6.5.1.01,10.02,7]tetradeca-2,4,6-triene-10-carboxylate
  参考文献：
  名称：

  A Triple Cascade Sequence as a Strategy for the Construction of the Erythrinane Skeleton

  摘要：

  alpha-Thiocarbocations generated from Pummerer reactions of several o-imido sulfoxides were intercepted by adjacent carbonyl groups to produce alpha-amido-substituted isobenzofurans as transient intermediates. When an olefinic tether was present, intramolecular Diels-Alder cycloaddition occurred followed by a ring-opening-elimination sequence that produced an N-acyliminium ion. Deprotonation of the iminium ion led to oxindole derivatives in good yields, When the iminium ion contained both a Mocking substituent, such as a carbomethoxy group, as a ell as an activated aromatic pi-tether, the N-acyliminium ion intermediate underwent stereoselective spirocyclization to afford cis-3,4-benzoerythrinane or homoerythrinane derivatives in good yield. The overall triple cascade sequence represents an efficient one-pot approach toward the erythrina skeleton in which the spirocyclic ABC skeleton is assembled in a single operation. The scope and limitations of the triple cascade were explored by varying both the olefinic and nucleophilic tethers. The required sulfoxide precursors for these Pummerer-induced transformations were easily synthesized starting from 2-[(ethylthio)methyl]benzoic acid. The tandem Pummerer/Diels-Alder/N-acyliminium ion cyclization was used for the synthesis of indoloisoquinoline 38. Since compound 38 was converted to 47 which, in turn, was transformed into erysotramidine (2), its preparation represents an extraordinarily facile, formal synthesis of this member of the Erythrina alkaloid family.

  DOI：

  10.1021/jo9716183
• 作为产物：
  描述：

  2-Ethylsulfanylmethyl-benzoic acid 在 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 2-(ethylsulfanylmethyl)-N-[2-(1H-indol-3-yl)ethyl]benzamide
  参考文献：
  名称：

  A Triple Cascade Sequence as a Strategy for the Construction of the Erythrinane Skeleton

  摘要：

  alpha-Thiocarbocations generated from Pummerer reactions of several o-imido sulfoxides were intercepted by adjacent carbonyl groups to produce alpha-amido-substituted isobenzofurans as transient intermediates. When an olefinic tether was present, intramolecular Diels-Alder cycloaddition occurred followed by a ring-opening-elimination sequence that produced an N-acyliminium ion. Deprotonation of the iminium ion led to oxindole derivatives in good yields, When the iminium ion contained both a Mocking substituent, such as a carbomethoxy group, as a ell as an activated aromatic pi-tether, the N-acyliminium ion intermediate underwent stereoselective spirocyclization to afford cis-3,4-benzoerythrinane or homoerythrinane derivatives in good yield. The overall triple cascade sequence represents an efficient one-pot approach toward the erythrina skeleton in which the spirocyclic ABC skeleton is assembled in a single operation. The scope and limitations of the triple cascade were explored by varying both the olefinic and nucleophilic tethers. The required sulfoxide precursors for these Pummerer-induced transformations were easily synthesized starting from 2-[(ethylthio)methyl]benzoic acid. The tandem Pummerer/Diels-Alder/N-acyliminium ion cyclization was used for the synthesis of indoloisoquinoline 38. Since compound 38 was converted to 47 which, in turn, was transformed into erysotramidine (2), its preparation represents an extraordinarily facile, formal synthesis of this member of the Erythrina alkaloid family.

  DOI：

  10.1021/jo9716183

文献信息

• A Triple Cascade Sequence as a Strategy for the Construction of the Erythrinane Skeleton
  作者：Albert Padwa、Rudiger Hennig、C. Oliver Kappe、Thomas S. Reger

  DOI：10.1021/jo9716183

  日期：1998.2.1

  alpha-Thiocarbocations generated from Pummerer reactions of several o-imido sulfoxides were intercepted by adjacent carbonyl groups to produce alpha-amido-substituted isobenzofurans as transient intermediates. When an olefinic tether was present, intramolecular Diels-Alder cycloaddition occurred followed by a ring-opening-elimination sequence that produced an N-acyliminium ion. Deprotonation of the iminium ion led to oxindole derivatives in good yields, When the iminium ion contained both a Mocking substituent, such as a carbomethoxy group, as a ell as an activated aromatic pi-tether, the N-acyliminium ion intermediate underwent stereoselective spirocyclization to afford cis-3,4-benzoerythrinane or homoerythrinane derivatives in good yield. The overall triple cascade sequence represents an efficient one-pot approach toward the erythrina skeleton in which the spirocyclic ABC skeleton is assembled in a single operation. The scope and limitations of the triple cascade were explored by varying both the olefinic and nucleophilic tethers. The required sulfoxide precursors for these Pummerer-induced transformations were easily synthesized starting from 2-[(ethylthio)methyl]benzoic acid. The tandem Pummerer/Diels-Alder/N-acyliminium ion cyclization was used for the synthesis of indoloisoquinoline 38. Since compound 38 was converted to 47 which, in turn, was transformed into erysotramidine (2), its preparation represents an extraordinarily facile, formal synthesis of this member of the Erythrina alkaloid family.