(2R,5R)-2-[2-[(4-heptylphenyl)methylsulfanyl]propan-2-yl]-5-methylcyclohexan-1-one | 407619-28-7

• 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: (2R,5R)-2-[2-[(4-heptylphenyl)methylsulfanyl]propan-2-yl]-5-methylcyclohexan-1-one
• CAS: 407619-28-7
• 化学式: C₂₄H₃₈OS
• 分子量: 374.631
• InChiKey: XBYJUWFUYYKDSQ-DENIHFKCSA-N

物化性质

• 沸点：
  484.0±20.0 °C(Predicted)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,5R)-2-[2-[(4-heptylphenyl)methylsulfanyl]propan-2-yl]-5-methylcyclohexan-1-one 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以97%的产率得到
  参考文献：
  名称：

  开发新型苯硫醇作为可回收的无味硫化氢替代品

  摘要：

  2,4,6-三甲氧基苄基硫醇 (4) 被开发为硫化氢的无味替代品，以在迈克尔加成中提供 β-巯基-羰基化合物并将烷基溴转化为烷硫醇。通过用三氟乙酸和甲苯的溶剂混合物处理，由 4 和 α,β-不饱和酯或酮制备的 -Michael 加合物的去三甲氧基苄基化很容易进行，得到 β-巯基羰基化合物。作为副产物获得的2,4,6-三甲氧基苄基异硫脲鎓盐的连续碱水解，伴随着二硫化物8以良好收率再生4。二硫化物8也通过用LiAlH 4 还原而转化为4。类似的方案适用于使用烷基溴的 SN 2 反应合成烷硫醇。

  DOI：

  10.1055/s-2007-984524
• 作为产物：
  描述：

  己基溴化镁 在 sodium hydroxide 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 23.0h， 生成 (2R,5R)-2-[2-[(4-heptylphenyl)methylsulfanyl]propan-2-yl]-5-methylcyclohexan-1-one
  参考文献：
  名称：

  Odorless substitutes for foul-smelling thiols: syntheses and applications

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(01)02024-x

文献信息

• 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.
• Development of a Novel Benzyl Mercaptan as a Recyclable Odorless Substitute of Hydrogen Sulfide
  作者：Manabu Node、Manabu Matoba、Tetsuya Kajimoto

  DOI：10.1055/s-2007-984524

  日期：2007.7

  odorless substitute of hydrogen sulfide to afford β-mercapto -carbonyl compounds in a Michael addition and to convert alkyl -bromides into alkanethiols. Detrimethoxybenzylation of the -Michael adducts prepared from 4 and α,β-unsaturated esters or -ketones was facilely carried out by treatment with a solvent mixture of trifluoroacetic acid and toluene to give β-mercapto carbonyl compounds. Successive

  2,4,6-三甲氧基苄基硫醇 (4) 被开发为硫化氢的无味替代品，以在迈克尔加成中提供 β-巯基-羰基化合物并将烷基溴转化为烷硫醇。通过用三氟乙酸和甲苯的溶剂混合物处理，由 4 和 α,β-不饱和酯或酮制备的 -Michael 加合物的去三甲氧基苄基化很容易进行，得到 β-巯基羰基化合物。作为副产物获得的2,4,6-三甲氧基苄基异硫脲鎓盐的连续碱水解，伴随着二硫化物8以良好收率再生4。二硫化物8也通过用LiAlH 4 还原而转化为4。类似的方案适用于使用烷基溴的 SN 2 反应合成烷硫醇。