[6-(2-Methoxycarbonyloxyethyl)-2,3-dimethylphenyl] trifluoromethanesulfonate | 869468-97-3

• 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: [6-(2-Methoxycarbonyloxyethyl)-2,3-dimethylphenyl] trifluoromethanesulfonate
• 英文别名: [6-(2-methoxycarbonyloxyethyl)-2,3-dimethylphenyl] trifluoromethanesulfonate
• CAS: 869468-97-3
• 化学式: C₁₃H₁₅F₃O₆S
• 分子量: 356.32
• InChiKey: GGCUPGIOLCRRLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [6-(2-Methoxycarbonyloxyethyl)-2,3-dimethylphenyl] 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 41.0h， 以52%的产率得到(6,7-Dimethyl-2,3-dihydroindol-1-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：

  在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 [6-(2-Methoxycarbonyloxyethyl)-2,3-dimethylphenyl] 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.