(-)-(1R,2S,5R)-2-[1-methyl-1-(phenylthio)ethyl]-5-methylcyclohexanol | 353511-37-2

• 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: (-)-(1R,2S,5R)-2-[1-methyl-1-(phenylthio)ethyl]-5-methylcyclohexanol
• 英文别名: (-)-(1R,2S,5S)-2-[1-methyl-1-(phenylthio)ethyl]-5-methylcyclohexanol；(1R,2S,5R)-5-methyl-2-(2-phenylsulfanylpropan-2-yl)cyclohexan-1-ol
• CAS: 353511-37-2
• 化学式: C₁₆H₂₄OS
• 分子量: 264.432
• InChiKey: DZILAPWMSOSACL-VHDGCEQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [MoO2Cl2(THF)2] 、 (-)-(1R,2S,5R)-2-[1-methyl-1-(phenylthio)ethyl]-5-methylcyclohexanol 以 二氯甲烷 为溶剂， 以74%的产率得到MoO2(THF)Cl[(-)-(1R,2S,5S)-2-[1-methyl-1-(phenylthio)ethyl]-5-methylcyclohexanolato]
  参考文献：
  名称：

  Chiral dioxomolybdenum(VI) complexes for enantioselective alkene epoxidation

  摘要：

  Chiral dioxomolybdenum(M) complexes of the type MoO2Cl2(L*) (L* = oxime), MoO2(THF)(2)L* (L* = cis-p-menthane-3,8-diol) and MoO2Cl(THF)L* (L* = 8-phenylthioneomenthol and 8-phenylthioisoneomenthol) have been prepared in good yields by reacting MoO2Cl2(THF)(2) with the appropriate chiral organic bidentate O,O-, O,N- and O,S-ligands. The complexes were characterised by solution NMR (H-1, C-13, Mo-95) and IR spectroscopy as well as elementary analysis, and were evaluated as catalysts in solution for the asymmetric epoxidation of cis-beta -methylstyrene by tert-butylhydroperoxide (TBHP). The cis-diol complex shows high catalytic activity and enantiomeric excesses of up to 25%. An attempt was made to immobilise the complex MoO2(THF)Cl[(-)-8-phenylthioneomenthol] within the channels of MCM-41 mesoporous silica by using a tethering ligand [L = NC(CH2)(3)Si(OEt)(3)]. The material was characterised by powder X-ray diffraction (XRD), IR spectroscopy and magic-angle-spinning (MAS) NMR (C-13, Si-29). Catalytic examinations demonstrated that it was active in the epoxidation of cyclooctene by TBHP. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00790-7
• 作为产物：
  描述：

  长叶薄荷酮 、 苯硫酚 在 sodium hydroxide 、 copper(I) bromide 、 锌 、 L-Selectride 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以20.7%的产率得到(-)-(1R,2S,5R)-2-[1-methyl-1-(phenylthio)ethyl]-5-methylcyclohexanol
  参考文献：
  名称：

  Chiral dioxomolybdenum(VI) complexes for enantioselective alkene epoxidation

  摘要：

  Chiral dioxomolybdenum(M) complexes of the type MoO2Cl2(L*) (L* = oxime), MoO2(THF)(2)L* (L* = cis-p-menthane-3,8-diol) and MoO2Cl(THF)L* (L* = 8-phenylthioneomenthol and 8-phenylthioisoneomenthol) have been prepared in good yields by reacting MoO2Cl2(THF)(2) with the appropriate chiral organic bidentate O,O-, O,N- and O,S-ligands. The complexes were characterised by solution NMR (H-1, C-13, Mo-95) and IR spectroscopy as well as elementary analysis, and were evaluated as catalysts in solution for the asymmetric epoxidation of cis-beta -methylstyrene by tert-butylhydroperoxide (TBHP). The cis-diol complex shows high catalytic activity and enantiomeric excesses of up to 25%. An attempt was made to immobilise the complex MoO2(THF)Cl[(-)-8-phenylthioneomenthol] within the channels of MCM-41 mesoporous silica by using a tethering ligand [L = NC(CH2)(3)Si(OEt)(3)]. The material was characterised by powder X-ray diffraction (XRD), IR spectroscopy and magic-angle-spinning (MAS) NMR (C-13, Si-29). Catalytic examinations demonstrated that it was active in the epoxidation of cyclooctene by TBHP. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00790-7