(5R)-2-methyl-5-propan-2-ylcyclohexan-1-ol | 1116694-68-8

• 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: (5R)-2-methyl-5-propan-2-ylcyclohexan-1-ol
• CAS: 1116694-68-8
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: ULJXKUJMXIVDOY-HWOCKDDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5R)-2-methyl-5-propan-2-ylcyclohexan-1-ol 在 ammonium cerium (IV) nitrate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以75%的产率得到(4R)-4-isopropyl-7-methyloxepan-2-one
  参考文献：
  名称：

  Synthetic studies on C14 cembranoids: synthesis of C4–12 fragment of sarcophytonolides E–G and L and C5–11 fragment of sarcophytonolide L

  摘要：

  An efficient stereoselective synthesis of C4-12 fragment of the cembranoids, sarcophytonolides E-G and L and C5-11 fragment of sarcophytonolide L is described. The C4-12 building block is efficiently assembled starting from chiral pool material (R)-carvone employing the Baeyer-Villiger oxidation, modified Knoevenagel condensation and asymmetric dihydroxylation as the key steps. The synthesis of C5-11 fragment is based on orthoester Johnson-Claisen rearrangement as the key step. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.093
• 作为产物：
  描述：

  (R)-香芹醇 在 10% palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以80%的产率得到(5R)-2-methyl-5-propan-2-ylcyclohexan-1-ol
  参考文献：
  名称：

  Synthetic studies on C14 cembranoids: synthesis of C4–12 fragment of sarcophytonolides E–G and L and C5–11 fragment of sarcophytonolide L

  摘要：

  An efficient stereoselective synthesis of C4-12 fragment of the cembranoids, sarcophytonolides E-G and L and C5-11 fragment of sarcophytonolide L is described. The C4-12 building block is efficiently assembled starting from chiral pool material (R)-carvone employing the Baeyer-Villiger oxidation, modified Knoevenagel condensation and asymmetric dihydroxylation as the key steps. The synthesis of C5-11 fragment is based on orthoester Johnson-Claisen rearrangement as the key step. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.093

文献信息

• A convenient methodology for the chemoselective reduction of a wide variety of functionalized alkenes
  作者：James H. Babler、Nicholas A. White

  DOI：10.1016/j.tetlet.2009.11.061

  日期：2010.1

  An efficient method to effect chemoselective reduction of alkenes (including trisubstituted olefins) possessing various sensitive and/or reducible groups such as acetals, allylic alcohols, benzyl ethers, epoxides, esters, halides, nitriles, and sulfones is reported. The reduction is facile at 0 °C in aqueous N,N-dimethylacetamide containing sodium borohydride in the presence of 15 mol % ruthenium(III)

  据报道，一种有效的方法可以实现对具有各种敏感和/或可还原基团（如缩醛，烯丙基醇，苄基醚，环氧化物，酯，卤化物，腈和砜）的烯烃（包括三取代的烯烃）进行化学选择性还原。在含有15mol％氯化钌（III）的情况下，在含硼氢化钠的N，N-二甲基乙酰胺水溶液中，在0℃下还原容易。如果双键的结构环境充分不同，则二烯的区域选择性还原也是可行的。
• Selective reduction of dienes/polyenes using sodium borohydride/catalytic ruthenium(III) in various liquid amide aqueous mixtures
  作者：James H. Babler、David W. Ziemke、Robert M. Hamer

  DOI：10.1016/j.tetlet.2013.01.083

  日期：2013.3

  structurally diverse dienes and an unsymmetrical triene is reported. The reduction is facile at 0 °C in a liquid amide aqueous solution containing sodium borohydride in the presence of 15 mol % ruthenium(III) chloride. The chemoselectivity of the reaction is controlled by proper choice of the liquid amide solvent.

  据报道，一种有效的方法可以选择性地还原几种结构不同的二烯和不对称的三烯。在含有硼氢化钠的液体酰胺水溶液中，在15摩尔％氯化钌（III）的存在下，还原在0°C时容易进行。该反应的化学选择性是由液体酰胺溶剂的适当选择来控制。