1(S)-5(S)-(+)-cis-sobrerol | 454-77-3

• 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: 1(S)-5(S)-(+)-cis-sobrerol
• 英文别名: (+)-cis-sobrerol；cis-sobrerol；(+)-cis-Sobrerol；(4S)-1-Methyl-4r-(α-hydroxy-isopropyl)-cyclohexen-(1)-ol-(6c)；(4S)-cis-p-Menthen-(1)-diol-(6.8)；cis-5-Hydroxy-alpha,alpha,4-trimethylcyclohex-3-ene-1-methanol；(1S,5S)-5-(2-hydroxypropan-2-yl)-2-methylcyclohex-2-en-1-ol
• CAS: 454-77-3
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: OMDMTHRBGUBUCO-IUCAKERBSA-N

物化性质

• 沸点：
  160 °C(Press: 12 Torr)
• 密度：
  1.051±0.06 g/cm3(Predicted)
• 熔点：
  108-108.5 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1(S)-5(S)-(+)-cis-sobrerol 在 乙醇 、 硫酸 、 镍 作用下， 生成 2β,6,6-trimethyl-7-oxabicyclo<3.2.1>octane
  参考文献：
  名称：

  Schmidt, Chemische Berichte, 1955, vol. 88, p. 459,466

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 反应 3.0h， 生成 1(S)-5(S)-(+)-cis-sobrerol 、 (-)-pinol
  参考文献：
  名称：

  Szalkowska-Pagowska, Hieronima; Piatkowski, Krzysztof, Polish Journal of Chemistry, 1985, vol. 59, # 5-6, p. 531 - 545

  摘要：

  DOI：

文献信息

• THE ENANTIOSELECTIVE BIOTRANSFORMATION OF α-TERPINEOL AND ITS ACETATE WITH THE CULTURED CELLS OF<i>NICOTIANA TABACUM</i>
  作者：Takayuki Suga、Toshifumi Hirata、Ym Sook Lee

  DOI：10.1246/cl.1982.1595

  日期：1982.10.5

  In the biotransformation of the enantiomers of p-menth-1-en-8-ol (α-terpineol) and 8-acetoxy-p-menth-1-ene (α-terpinyl acetate) with the cultured suspension cells of Nicotiana tabacum, it was clarified that the cultured cells effected the hydroxylation at the 6-position of (4R)-(+)-enantiomer in preference to the (4S)-(−)-enantiomer, whereas the cells did the hydrolysis of the acetoxyl group and the

  p-menth-1-en-8-ol (α-terpineol) 和 8-acetoxy-p-menth-1-ene (α-terpinyl acetate) 的对映异构体与烟草悬浮细胞的生物转化，澄清的是，培养的细胞在 (4R)-(+)-对映体的 6-位进行羟基化优先于 (4S)-(-)-对映体，而细胞进行乙酰氧基的水解和(4S)-(-)-α-松油醇乙酸酯的烯键羟基化优先于(4R)-(+)-对映异构体。
• Delepine; Horeau; Grandperrin-Harispe, Annales de Chimie (Cachan, France), 1943, vol. <11> 18, p. 250,254
  作者：Delepine、Horeau、Grandperrin-Harispe

  DOI：——

  日期：——
• Schmidt, Chemische Berichte, 1960, vol. 93, p. 2485,2490
  作者：Schmidt

  DOI：——

  日期：——
• Stereocontrolled regiospecificity of the water loss fromtrans-sobrerol radical cation upon electron ionization
  作者：Antonio Selva、Francesco Ferrario、Paolo Ventura、Renato Pellegata

  DOI：10.1002/oms.1210220809

  日期：1987.8

  AbstractWater loss from frans‐sobrerol upon electron impact ionization selectively involves the tertiary OH group, predominantly occurring by a stereocontrolled H‐transfer from C(5) position in a rate‐determining step process, as proved by 18O and deuterium labelling. Monomethyl ethers behave accordingly. Ionic structures of the water‐loss product or products are investigated by metastable ion and collision activation mass‐analysed ion kinetic energy spectroscopy, using model ions generated from some substrates, which are chemically related to fralts‐sobrerol in condensed phase, i.e. α‐pinane epoxide, cis‐sobrerol and pinol. A substantial conversion of cis‐sobrerol molecular ions to ionized pinol by loss of water has been demonstrated.
• Schmidt, Chemische Berichte, <hi>1953</hi>, vol. 86, p. 1437,1443
  作者：Schmidt

  DOI：——

  日期：——