3-((R)-3-Isopropyl-1-methyl-2-trifluoromethanesulfonyloxy-cyclopent-2-enyl)-propionic acid methyl ester | 868615-48-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 3-((R)-3-Isopropyl-1-methyl-2-trifluoromethanesulfonyloxy-cyclopent-2-enyl)-propionic acid methyl ester
• CAS: 868615-48-9
• 化学式: C₁₄H₂₁F₃O₅S
• 分子量: 358.379
• InChiKey: RQLZXIKRMIZPIQ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-((R)-3-Isopropyl-1-methyl-2-trifluoromethanesulfonyloxy-cyclopent-2-enyl)-propionic acid methyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以80%的产率得到3-((R)-3-Isopropyl-1-methyl-2-trifluoromethanesulfonyloxy-cyclopent-2-enyl)-propionic acid
  参考文献：
  名称：

  Asymmetric synthesis of the tricyclic core of cyathin diterpenoids via intramolecular Heck reaction

  摘要：

  The enantioselective synthesis of the ketones 3 which displays the carbon core of NGF-inducing cyathane diterpenes is described. The key tricyclic trienone 22 was assembled in 13 steps from Michael adduct (R)-8a via intramolecular Heck cyclization of the chiral triflate 21. The trienone 22 was further elaborated into ketone 3 through tritnethylaluminum-promoted expansion of the Gring with trimethylsilyldiazomethane. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.157
• 作为产物：
  描述：

  methyl 3-[(1R,3E)-3-ethylidene-1-methyl-2-oxocyclopentyl]propanoate 在 2,6-二叔丁基吡啶 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 17.0h， 生成 3-((R)-3-Isopropyl-1-methyl-2-trifluoromethanesulfonyloxy-cyclopent-2-enyl)-propionic acid methyl ester
  参考文献：
  名称：

  Asymmetric synthesis of the tricyclic core of cyathin diterpenoids via intramolecular Heck reaction

  摘要：

  The enantioselective synthesis of the ketones 3 which displays the carbon core of NGF-inducing cyathane diterpenes is described. The key tricyclic trienone 22 was assembled in 13 steps from Michael adduct (R)-8a via intramolecular Heck cyclization of the chiral triflate 21. The trienone 22 was further elaborated into ketone 3 through tritnethylaluminum-promoted expansion of the Gring with trimethylsilyldiazomethane. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.07.157