(R)-10-methyl-1-(benzyl)undecyl acetate | 159690-66-1

• 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)-10-methyl-1-(benzyl)undecyl acetate
• 英文别名: [(2R)-11-methyl-1-phenyldodecan-2-yl] acetate
• CAS: 159690-66-1
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: PTDBLRXJTKWJFG-OAQYLSRUSA-N

物化性质

• 沸点：
  403.634±14.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.934±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-10-methyl-1-(benzyl)undecyl acetate 在 ruthenium trichloride 、 sodium hydroxide 、 sodium periodate 作用下， 以 四氯化碳 、 乙醇 、 乙腈 为溶剂， 反应 8.5h， 生成 (R)-3-Hydroxy-12-methyl-tridecanoic acid
  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：

  (R)-7-benzyloxacycloheptan-2-one 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 氢气 、 4-甲基苯磺酸吡啶 、 lithium 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 (R)-10-methyl-1-(benzyl)undecyl acetate
  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