cis-1,3-Dimethyl-cyclohexandiol-(1,3) | 128749-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1,3-Dimethyl-cyclohexandiol-(1,3)
• 英文别名: 1r.3c-dimethyl-cyclohexanediol-(1.3t)；1r.3c-Dimethyl-cyclohexandiol-(1.3t)；(1R,3S)-1,3-dimethylcyclohexane-1,3-diol
• CAS: 128749-93-9
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: RYQYTYXVZCAYPW-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1,3-Dimethyl-cyclohexandiol-(1,3) 在 boron trioxide 作用下， 生成
  参考文献：
  名称：

  Replacement of Hydrogen at a Tertiary Carbon Atom with OH by Alkaline Permanganate¹

  摘要：

  DOI：

  10.1021/ja01501a033
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 在 硫酸 作用下， 生成 cis-1,3-Dimethyl-cyclohexandiol-(1,3)
  参考文献：
  名称：

  Cyclizations Accompanying the Hydration and the Dehydration of β-Methylheptenone

  摘要：

  DOI：

  10.1021/ja01586a033

文献信息

• Selective C–H bond hydroxylation of cyclohexanes in water by supramolecular control
  作者：Bin Yang、Jian-Fang Cui、Man Kin Wong

  DOI：10.1039/c7ra03930a

  日期：——

  A new approach for selective hydroxylation of non-activated cyclohexanes using dioxirane generated in situ in water through supramolecular control has been developed. Using β-CD and γ-CD as the supramolecular hosts, selective hydroxylation of cyclohexane substrates, including trans/cis-1,4-, 1,3- and 1,2-dimethylcyclohexanes and trans/cis-decahydronaphthalene, was achieved in up to 54% yield in water

  已经开发出一种新的方法，该方法使用超分子控制在水中原位生成的二环氧乙烷选择性活化非活化环己烷。使用β-CD和γ-CD作为超分子主体，可实现环己烷底物的选择性羟基化，包括反式/顺式-1,4-，1,3-和1,2-二甲基环己烷以及反式/顺式十氢萘水中的收率达到54％。此外，通过与水中的β-CD和γ-CD进行包合络合，阻止了二环氧乙烷与具有较高空间位阻的C-H键的连接，从而实现了（+）-薄荷醇的位点选择性C-H键羟基化。
• Cyclohexane-based 1,3-dipodands: complexation and conformational biasing
  作者：Shailaja M. Shirodkar、Gary R. Weisman

  DOI：10.1039/c39890000236

  日期：——

  Cyclohexane-based cis-1,3-dipodand (1) undergoes ring inversion to a diaxial conformation upon Na+ complexation, while related diaxially biased dipodand (2) is a better host.

  基于环己烷的顺-1,3-二足体（1）在Na +络合后经历环反转成双轴构象，而相关的双轴偏置二足体（2）是更好的宿主。
• Selective functionalization of hydrocarbons. 6. Mechanistic and preparative studies on the regio- and stereoselective paraffin hydroxylation with peracids
  作者：Hans Joerg Schneider、Walter Mueller

  DOI：10.1021/jo00223a036

  日期：1985.11
• The Synthesis and Acid-catalyzed Cyclization of α-Methylheptenone
  作者：Jerrold Meinwald、John A. Yankeelov

  DOI：10.1021/ja01552a062

  日期：1958.10
• Stereoselective dioxirane hydroxylations and the synthesis of tripod boronic acid esters
  作者：Lucia D’Accolti、Michele Fiorentino、Caterina Fusco、Francesco Capitelli、Ruggero Curci

  DOI：10.1016/j.tetlet.2007.03.101

  日期：2007.5

  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.