(R)-1-phenyl-2-octanol | 159690-72-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-1-phenyl-2-octanol
• 英文别名: (R)-1-phenyloctan-2-ol；(2R)-1-phenyloctan-2-ol
• CAS: 159690-72-9
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: AWLDTWVEFFLZOO-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-1-phenyl-2-octanol 在 吡啶 、 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 、 lithium aluminium tetrahydride 作用下， 以 四氯化碳 、 乙醚 、 乙醇 、 乙腈 为溶剂， 反应 12.5h， 生成 (R)-(-)-1,3-壬烷二醇
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2
• 作为产物：
  描述：

  在 吡啶 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 (R)-1-phenyl-2-octanol
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2

文献信息

• Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes
  作者：Lichao Fang、Lu Yan、Fredrik Haeffner、James P. Morken

  DOI：10.1021/jacs.5b13174

  日期：2016.3.2

  Catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts. Mechanistic experiments suggest the intermediacy of 1,2-bonded diboronates.

  烯烃的催化对映选择性二硼化是通过容易获得的碳水化合物衍生的催化剂来完成的。机理实验表明 1,2-键合二硼酸盐具有中间作用。
• Application of microbial enantiofacially selective hydrolysis in natural product synthesis
  作者：Osamu Katoh、Takeshi Sugai、Hiromichi Ohta

  DOI：10.1016/s0957-4166(00)86269-2

  日期：1994.10

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.