cis,trans-3,5-Dimethylcyclohexanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis,trans-3,5-Dimethylcyclohexanol
• 英文别名: (+/-)-1r,3t-Dimethyl-cyclohexanol-(5)；Cis,trans,trans-3,5-dimethylcyclohexanol；(3R,5R)-3,5-dimethylcyclohexan-1-ol
• 化学式: C₈H₁₆O
• 分子量: 128.214
• InChiKey: WIYNOPYNRFPWNB-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  0
• 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：

  cis,trans-3,5-Dimethylcyclohexanol 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (S)-2-((3R,5R)-3,5-Dimethyl-cyclohexyloxycarbonylamino)-hexanoic acid
  参考文献：
  名称：

  A structural screening approach to ketoamide-based inhibitors of cathepsin K

  摘要：

  Several novel ketoamide-based inhibitors of cathepsin K have been identified. Starting from a modestly potent inhibitor, structural screening of P-2 elements led to 100-fold enhancements in inhibitory activity. Modifications to one of these leads resulted in an orally bioavailable cathepsin K inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.023
• 作为产物：
  描述：

  trans-3,5-dimethylcyclohexanone 在 lithium aluminium tetrahydride 作用下， 生成 cis,trans-3,5-Dimethylcyclohexanol
  参考文献：
  名称：

  Conformational Analysis. XII.¹ Acetylation Rates of Substituted Cyclohexanols. The Kinetic Method of Conformational Analysis

  摘要：

  DOI：

  10.1021/ja00966a028

文献信息

• Transfer hydrogenation of ketones with [Ru4H3(CO)12]? as the precatalyst
  作者：Sumit Bhaduri、Krishna Sharma、Doble Mukesh

  DOI：10.1039/dt9930001191

  日期：——

  The cluster [N(PPh3)2] [Ru4H3(CO)12] 1a has been found to be an efficient precatalyst for the transfer hydrogenations of ketones and alpha,beta-unsaturated ketones. With substrates such as (5S)-carvone [2-methyl-5-(1-methylethenyl)cyclohex-2-en-1-one], (3R)-methylcyclopentanone and (3R)-methyl-cyclohexanone, moderate to high diastereoselectivities were observed for reduction of the conjugated olefinic and ketonic functionalities respectively. Aromatisation of carvone to 5-isopropyl-2-methylphenol and disproportionation of cyclohex-2-en-1-one to phenol and cyclohexanone have also been found to be catalysed by 1a. Studies with radical inhibitors and other evidence suggest a radical mechanism for the transfer-hydrogenation and aromatisation reactions. In the transfer hydrogenation of cyclohex-2-en-1-one, the rate of conversion of 1a into other soluble species can be modelled accurately if autocatalysis is assumed. The time-dependent concentration profiles of cyclohex-2-en-1-one, cyclohexanone and cyclohexanol are simulated well if autocatalytic formation of an active intermediate followed by consecutive reactions leading to the formation of products is assumed. Such a model is also consistent with the proposed radical mechanism.
• Skita; Faust, Chemische Berichte, 1939, vol. 72, p. 1127,1136
  作者：Skita、Faust

  DOI：——

  日期：——
• Conformational Analysis. XII.¹ Acetylation Rates of Substituted Cyclohexanols. The Kinetic Method of Conformational Analysis
  作者：Ernest L. Eliel、Francis J. Biros

  DOI：10.1021/ja00966a028

  日期：1966.7
• A structural screening approach to ketoamide-based inhibitors of cathepsin K
  作者：David G. Barrett、John G. Catalano、David N. Deaton、Stacey T. Long、Robert B. McFadyen、Aaron B. Miller、Larry R. Miller、Kevin J. Wells-Knecht、Lois L. Wright

  DOI：10.1016/j.bmcl.2005.03.023

  日期：2005.5

  Several novel ketoamide-based inhibitors of cathepsin K have been identified. Starting from a modestly potent inhibitor, structural screening of P-2 elements led to 100-fold enhancements in inhibitory activity. Modifications to one of these leads resulted in an orally bioavailable cathepsin K inhibitor. (c) 2005 Elsevier Ltd. All rights reserved.