((1R,2S,1'S,2'S,1''R,2''S)-2''-Hydroxymethyl-[1,1';2',1'']tercyclopropan-2-yl)-methanol | 183786-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((1R,2S,1'S,2'S,1''R,2''S)-2''-Hydroxymethyl-[1,1';2',1'']tercyclopropan-2-yl)-methanol
• 英文别名: [(1S,2R)-2-[(1S,2S)-2-[(1R,2S)-2-(hydroxymethyl)cyclopropyl]cyclopropyl]cyclopropyl]methanol
• CAS: 183786-79-0
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: JDGWBFBOYFBTLQ-VFZPANTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((1R,2S,1'S,2'S,1''R,2''S)-2''-Hydroxymethyl-[1,1';2',1'']tercyclopropan-2-yl)-methanol 在 重铬酸吡啶 、 4 A molecular sieve 、 Celite 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-3-[(1S,2R,1'S,2'S,1''S,2''R)-2''-((E)-3-Hydroxy-propenyl)-[1,1';2',1'']tercyclopropan-2-yl]-prop-2-en-1-ol
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-U-106305

  摘要：

  DOI：

  10.1021/ja9619420
• 作为产物：
  描述：

  diethyl (±)-(2E,2′E)-3,3′-(1R,2R)-cyclopropane-1,2-diylbisprop-2-enoate 在 L-tartrate-derived dioxaboralane 、 diethylzinc 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 ((1R,2S,1'S,2'S,1''R,2''S)-2''-Hydroxymethyl-[1,1';2',1'']tercyclopropan-2-yl)-methanol
  参考文献：
  名称：

  Two-Directional Synthesis of Polycyclopropanes. An Approach to the Quinquecyclopropane Fragment of U-106305

  摘要：

  The stereoselective preparation of three stereoisomeric tercyclopropanes and a quinquecyclopropane was investigated. Two of the tercyclopropanes were C-2-symmetric and were prepared efficiently through the two-directional application of Charette's reagent-stereocontrolled cyclopropanation methodology. The nonsymmetric tercyclopropane was prepared by an iterative one-directional application of the same reagent-mediated cyclopropanation method. It was shown that the reagent-controlled transformations are far more effective for the stereoselective preparation of the tercyclopropanes than are the reactions which rely upon the influence of the substrate stereocenters. A C-2-symmetric quinquecyclopropane, which possesses the repeating trans-syn stereochemistry, was prepared by iterative application of the two-directional strategy.

  DOI：

  10.1021/jo961136b