3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-propionic acid | 467242-38-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-propionic acid
• 英文别名: 3-[(1R)-2-[tert-butyl(dimethyl)silyl]oxy-1-methylcyclopentyl]propanoic acid
• CAS: 467242-38-2
• 化学式: C₁₅H₃₀O₃Si
• 分子量: 286.487
• InChiKey: GQOSIKCQLDTVFL-WPZCJLIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-propionic acid 在 tris(dibenzylideneacetone)dipalladium (0) lead(IV) acetate 、 2,6-二叔丁基吡啶 、 草酰氯 、 四丁基氟化铵 、 碘 、 二甲基亚砜 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 9.0h， 生成 methyl (3aR,5aR,8R,9aS)-8-acetyloxy-3a-methyl-3,4,5,8,9,9a-hexahydro-2H-cyclopenta[a]naphthalene-5a-carboxylate
  参考文献：
  名称：

  Synthetic studies toward cyathin diterpenoids: approach to the tricyclic system through intramolecular Heck-type cyclization

  摘要：

  The enantioselective synthesis of a model of the core ring system of cyathin diterpenes is described. The key tricyclic acetate 4 was assembled via an intramolecular Heck-type cyclization of the chiral triflate 8. Acetate 4 was taken through to model cyathan ketones 3a and 3b by a one-carbon ring expansion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00570-1
• 作为产物：
  描述：

  methyl (R)-3-(1-methyl-2-oxocyclopentyl)propanoate 在 氢氧化钾 、 sodium tetrahydroborate 、 米帕明 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-cyclopentyl]-propionic acid
  参考文献：
  名称：

  Synthetic studies toward cyathin diterpenoids: approach to the tricyclic system through intramolecular Heck-type cyclization

  摘要：

  The enantioselective synthesis of a model of the core ring system of cyathin diterpenes is described. The key tricyclic acetate 4 was assembled via an intramolecular Heck-type cyclization of the chiral triflate 8. Acetate 4 was taken through to model cyathan ketones 3a and 3b by a one-carbon ring expansion. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00570-1

文献信息

• Synthetic studies toward cyathin diterpenoids: approach to the tricyclic system through intramolecular Heck-type cyclization
  作者：Cyrille Thominiaux、Angèle Chiaroni、Didier Desmaële

  DOI：10.1016/s0040-4039(02)00570-1

  日期：2002.5

  The enantioselective synthesis of a model of the core ring system of cyathin diterpenes is described. The key tricyclic acetate 4 was assembled via an intramolecular Heck-type cyclization of the chiral triflate 8. Acetate 4 was taken through to model cyathan ketones 3a and 3b by a one-carbon ring expansion. (C) 2002 Elsevier Science Ltd. All rights reserved.