2,2-Dimethyl-propionic acid (R)-2-((1R,2S,6R)-2-hydroxy-6-isopropenyl-4-methyl-cyclohex-3-enyl)-propyl ester | 199661-64-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,2-Dimethyl-propionic acid (R)-2-((1R,2S,6R)-2-hydroxy-6-isopropenyl-4-methyl-cyclohex-3-enyl)-propyl ester
• 英文别名: [(2R)-2-[(1R,2S,6R)-2-hydroxy-4-methyl-6-prop-1-en-2-ylcyclohex-3-en-1-yl]propyl] 2,2-dimethylpropanoate
• CAS: 199661-64-8
• 化学式: C₁₈H₃₀O₃
• 分子量: 294.434
• InChiKey: MQFFDJAUADRBPU-JONQDZQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  2,2-Dimethyl-propionic acid (R)-2-((1R,2S,6R)-2-hydroxy-6-isopropenyl-4-methyl-cyclohex-3-enyl)-propyl ester 在 正丁基锂 、 四丙基高钌酸铵 、 4 A molecular sieve 、 二异丁基氢化铝 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.75h， 生成 (2R)-7-[tert-butyl(dimethyl)silyl]oxy-2-[(1R,2S,6R)-2-(methoxymethoxy)-4-methyl-6-prop-1-en-2-ylcyclohex-3-en-1-yl]hept-4-yn-3-ol
  参考文献：
  名称：

  Total Synthesis of Zoanthamine Alkaloids, Part 2. Construction of the C1-C5, C6-C10, and C11-C24 Fragments of Zoanthamine.

  摘要：

  This paper describes the construction of three key intermediates 11, 15 and 23 for a projected total synthesis of the marine alkaloid zoanthamine. These building blocks, corresponding to the C-1-C-5, C-6-C-10, and C-11-C-24 fragments of the target molecule, are synthesised efficiently from (R)-gamma-hydroxymethyl-gamma-butyrolactone, methyl propiolate, and (S)-perillyl alcohol, respectively.

  DOI：

  10.3891/acta.chem.scand.51-1217
• 作为产物：
  描述：

  (3R,3aR,4R,7aS)-4-Isopropenyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.0h， 生成 2,2-Dimethyl-propionic acid (R)-2-((1R,2S,6R)-2-hydroxy-6-isopropenyl-4-methyl-cyclohex-3-enyl)-propyl ester
  参考文献：
  名称：

  Total Synthesis of Zoanthamine Alkaloids, Part 2. Construction of the C1-C5, C6-C10, and C11-C24 Fragments of Zoanthamine.

  摘要：

  This paper describes the construction of three key intermediates 11, 15 and 23 for a projected total synthesis of the marine alkaloid zoanthamine. These building blocks, corresponding to the C-1-C-5, C-6-C-10, and C-11-C-24 fragments of the target molecule, are synthesised efficiently from (R)-gamma-hydroxymethyl-gamma-butyrolactone, methyl propiolate, and (S)-perillyl alcohol, respectively.

  DOI：

  10.3891/acta.chem.scand.51-1217

文献信息

• Cu-mediated Stille reactions of sterically congested fragments: towards the total synthesis of zoanthamine
  作者：Thomas E. Nielsen、Sebastian Le Quement、Martin Juhl、David Tanner

  DOI：10.1016/j.tet.2005.06.005

  日期：2005.8

  A study on the Stille reaction of alkenyl iodides and starmanes with structural resemblance to retrosynthetic fragments of a projected total synthesis of the marine alkaloid zoanthamine was carried out. A range of reaction conditions was examined, and a protocol developed by Corey utilizing excess copper(I) chloride and lithium chloride was found to be most efficient. The methodology was successfully applied to join two major fragments of the zoanthamine skeleton. (c) 2005 Elsevier Ltd. All rights reserved.
• Total Synthesis of Zoanthamine Alkaloids, Part 2. Construction of the C1-C5, C6-C10, and C11-C24 Fragments of Zoanthamine.
  作者：David Tanner、Lars Tedenborg、Peter Somfai、Lars Skattebøl、Connie N. Rosendahl

  DOI：10.3891/acta.chem.scand.51-1217

  日期：——

  This paper describes the construction of three key intermediates 11, 15 and 23 for a projected total synthesis of the marine alkaloid zoanthamine. These building blocks, corresponding to the C-1-C-5, C-6-C-10, and C-11-C-24 fragments of the target molecule, are synthesised efficiently from (R)-gamma-hydroxymethyl-gamma-butyrolactone, methyl propiolate, and (S)-perillyl alcohol, respectively.