[4-(2-Methoxycarbonyloxyethyl)-3-methyl-1-(4-methylphenyl)sulfonylindol-5-yl] trifluoromethanesulfonate | 869468-99-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [4-(2-Methoxycarbonyloxyethyl)-3-methyl-1-(4-methylphenyl)sulfonylindol-5-yl] trifluoromethanesulfonate
• 英文别名: [4-(2-methoxycarbonyloxyethyl)-3-methyl-1-(4-methylphenyl)sulfonylindol-5-yl] trifluoromethanesulfonate
• CAS: 869468-99-5
• 化学式: C₂₁H₂₀F₃NO₈S₂
• 分子量: 535.519
• InChiKey: DIIFXVBOBUBWGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [4-(2-Methoxycarbonyloxyethyl)-3-methyl-1-(4-methylphenyl)sulfonylindol-5-yl] trifluoromethanesulfonate 、 苯甲酰胺 在 tris(dibenzylideneacetone)dipalladium (0) 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以96%的产率得到[1-Methyl-3-(4-methylphenyl)sulfonyl-7,8-dihydropyrrolo[3,2-e]indol-6-yl]-phenylmethanone
  参考文献：
  名称：

  A Domino Amidation Route to Indolines and Indoles:  Rapid Syntheses of Anhydrolycorinone, Hippadine, Oxoassoanine, and Pratosine

  摘要：

  When subjected to palladium-catalyzed amidation conditions, 2-triflyloxy phenethyl carbonates undergo, in addition to the expected aryl cross-coupling, an additional amidation with net displacement of the carbonate. The result is a one-step synthesis of indolines which may be oxidized to indoles. The utility of the procedure is illustrated by the two- or three-step syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.

  DOI：

  10.1021/ol052086c
• 作为产物：
  描述：

  [3-Methyl-1-(4-methylphenyl)sulfonyl-4-(2-oxoethyl)indol-5-yl] trifluoromethanesulfonate 在 吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 [4-(2-Methoxycarbonyloxyethyl)-3-methyl-1-(4-methylphenyl)sulfonylindol-5-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  A Domino Amidation Route to Indolines and Indoles:  Rapid Syntheses of Anhydrolycorinone, Hippadine, Oxoassoanine, and Pratosine

  摘要：

  When subjected to palladium-catalyzed amidation conditions, 2-triflyloxy phenethyl carbonates undergo, in addition to the expected aryl cross-coupling, an additional amidation with net displacement of the carbonate. The result is a one-step synthesis of indolines which may be oxidized to indoles. The utility of the procedure is illustrated by the two- or three-step syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.

  DOI：

  10.1021/ol052086c

文献信息

• A Domino Amidation Route to Indolines and Indoles:  Rapid Syntheses of Anhydrolycorinone, Hippadine, Oxoassoanine, and Pratosine
  作者：Michael D. Ganton、Michael A. Kerr

  DOI：10.1021/ol052086c

  日期：2005.10.1

  When subjected to palladium-catalyzed amidation conditions, 2-triflyloxy phenethyl carbonates undergo, in addition to the expected aryl cross-coupling, an additional amidation with net displacement of the carbonate. The result is a one-step synthesis of indolines which may be oxidized to indoles. The utility of the procedure is illustrated by the two- or three-step syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.