1,3,5-trimethyl-cyclohexane-1,3,5-triol | 940912-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,5-trimethyl-cyclohexane-1,3,5-triol
• CAS: 940912-19-6
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: QJEBHEQVVLFNIE-AYMMMOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,3,5-trimethyl-cyclohexane-1,3,5-triol 在 吡啶 、 三氯化硼 作用下， 以 氯仿 为溶剂， 反应 10.0h， 以92%的产率得到3,5,7-trimethyl-2,8,9-trioxa-1-boratricyclo[3.3.1.1^3,7]decane
  参考文献：
  名称：

  Stereoselective dioxirane hydroxylations and the synthesis of tripod boronic acid esters

  摘要：

  Methyl(trifluoromethyl)dioxirane (TFDO, 1b), a powerful yet selective oxidant, was employed to achieve in high yield the direct stereoselective hydroxylation at tert-CH of cis,cis-1,3,5-trimethylcyclohexane (4), yielding triol 7 bearing all-axial disposition of the three OH groups. Similarly, TFDO oxidation of 1,3- and of 1,4-dimethylcyclohexane gave the corresponding Z-diols 5 and 6, respectively. Triol 7 was a convenient starting material to synthesize a novel borate-that is, 1-bora-2,8,9-trioxa-3,5,7-trimethyl-adamantane (8)-having a peculiar cage-shaped 'tripod' structure. From triol 7, novel tripod arylboronic Bronsted-assisted Lewis acids (BLA) could be obtained, as exemplified by 10a and 10b. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.101
• 作为产物：
  描述：

  1,cis-3,cis-5-Trimethylcyclohexane 在 甲基(三氟甲基)-1,3-二环氧丙烷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到1,3,5-trimethyl-cyclohexane-1,3,5-triol
  参考文献：
  名称：

  Stereoselective dioxirane hydroxylations and the synthesis of tripod boronic acid esters

  摘要：

  Methyl(trifluoromethyl)dioxirane (TFDO, 1b), a powerful yet selective oxidant, was employed to achieve in high yield the direct stereoselective hydroxylation at tert-CH of cis,cis-1,3,5-trimethylcyclohexane (4), yielding triol 7 bearing all-axial disposition of the three OH groups. Similarly, TFDO oxidation of 1,3- and of 1,4-dimethylcyclohexane gave the corresponding Z-diols 5 and 6, respectively. Triol 7 was a convenient starting material to synthesize a novel borate-that is, 1-bora-2,8,9-trioxa-3,5,7-trimethyl-adamantane (8)-having a peculiar cage-shaped 'tripod' structure. From triol 7, novel tripod arylboronic Bronsted-assisted Lewis acids (BLA) could be obtained, as exemplified by 10a and 10b. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.101