(1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol | 79563-67-0

• 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: (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol
• 英文别名: (1S,2R,5R)-5-methyl-2-(2-sulfanylpropan-2-yl)cyclohexan-1-ol
• CAS: 79563-67-0
• 化学式: C₁₀H₂₀OS
• 分子量: 188.334
• InChiKey: BQQNGLUIXGYKQB-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 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：
  21.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 5.3h， 生成
  参考文献：
  名称：

  Asymmetric acetalization: a simple method for the synthesis of chiral a-monosubstituted cyclopentanones

  摘要：

  Acetalization of alpha-monosubstituted cyclopentanones with chiral hydroxy thiols under equilibrating conditions afforded a mixture of acetals in a highly diastereoselective manner, and deacetalization of the product affords optically active alpha-monosubstituted cyclopentanones.

  DOI：

  10.1021/jo00074a002
• 作为产物：
  描述：

  长叶薄荷酮 在 甲醇 、 sodium hydroxide 、 sodium 作用下， 以 四氢呋喃 、 乙醚 、 氨 为溶剂， 反应 23.5h， 生成 (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol
  参考文献：
  名称：

  高对映体纯度的（）-（+）-乙基甲基-丙基甲醇的不对称合成。衍生自（+）-普勒高酮的1,3-氧杂蒽酮作为手性佐剂

  摘要：

  通过将苄基硫醇1,4-加成至（+）-普勒高酮，然后用Na / NH 3还原并使所得的羟基硫醇与多聚甲醛缩合，可以制备手性，构象锁定的1，3-氧杂蒽。该手性佐剂的效用以93％ee中标题化合物的不对称合成为例

  DOI：

  10.1016/s0040-4039(01)81768-8

文献信息

• Radical cyclization using a thioacetal group for radical generation
  作者：Atsushi Nishida、Norio Kawahara、Mayumi Nishida、Osamu Yonemitsu

  DOI：10.1016/0040-4020(96)00511-x

  日期：1996.7

  The generation and cyclization of several heterocyclic radicals were investigated. The hydrogen abstraction from 1,3-dithiane, 1,3-dithiolane, and 1,3-oxathiane rings by a benzophenone triplet generated the corresponding heterocyclic radicals, which gave the cyclized products by intramolecular addition to α,β-unsaturated esters. Diastereoselective radical cyclization using chiral acetals was also investigated

  研究了几种杂环基的产生和环化。通过二苯甲酮三联体从1,3-二硫杂环戊烷，1,3-二硫杂环戊烷和1,3-氧杂蒽环上夺氢产生了相应的杂环基，这些杂环基通过分子内加成α，β-不饱和酯而得到环化产物。还研究了使用手性缩醛的非对映选择性自由基环化。
• Development of Odorless Thiols and Sulfides and Their Applications to Organic Synthesis
  作者：Kiyoharu Nishide、Shin-ichi Ohsugi、Tetsuo Miyamoto、Kamal Kumar、Manabu Node

  DOI：10.1007/s00706-003-0122-1

  日期：2004.2.1

  Development of new odorless thiols (dodecanethiol, 4- n -heptylphenylmethanethiol, 4-trimethylsilylphenylmethanethiol, 4-trimethylsilylbenzenethiol) and an odorless sulfide (1-methylsulfanyldodecane) and their applications to dealkylation, Michael addition, Swern oxidation, and Corey - Kim oxidation are described.

  描述了新型无味硫醇（十二烷硫醇，4- 正 庚基苯基甲硫醇，4-三甲基甲硅烷基苯基甲硫醇，4-三甲基甲硅烷基苯硫醇）和无味硫化物（1-甲基硫烷基十二烷 ）的开发及其在脱烷基， 迈克尔 加成， Swern 氧化和 科里 - 金 氧化中的应用。 。
• Odorless substitutes for foul-smelling thiols: syntheses and applications
  作者：Manabu Node、Kamal Kumar、Kiyoharu Nishide、Shin-ichi Ohsugi、Tetsuo Miyamoto

  DOI：10.1016/s0040-4039(01)02024-x

  日期：2001.12

  Several alkanethiols and p-alkylphenylmethanethiols were synthesized, and their odors were compared with those of ethanethiol and benzyl mercaptan by human and instrumental sensors. Among the various thiols analyzed. 1-dodecanethiol (1) and p-heptylphenylmethanethiol (3) were revealed to be odorless. 1-Dodecanethiol (1) has been used instead of ethanethiol for dealkylation of ethers, and p-heptylphenylmethanethiol (3) can replace benzyl mercaptan in the preparation of a 1,3-mercapto alcohol from an alpha,beta -unsaturated ketone. These odorless thiols will greatly improve the physical environment of the researcher working with these foul-smelling compounds. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Eliel, Ernest L., Phosphorus and Sulfur and the Related Elements, 1985, vol. 24, p. 73 - 96
  作者：Eliel, Ernest L.

  DOI：——

  日期：——