2,2-Dimethyl-propionic acid (E)-(S)-5-hydroxy-1-methyl-dec-6-enyl ester | 189069-58-7

• 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: 2,2-Dimethyl-propionic acid (E)-(S)-5-hydroxy-1-methyl-dec-6-enyl ester
• 英文别名: [(E,6S)-6-hydroxyundec-7-en-2-yl] 2,2-dimethylpropanoate
• CAS: 189069-58-7
• 化学式: C₁₆H₃₀O₃
• 分子量: 270.412
• InChiKey: YSRRVGAGUXVGIO-KOMLVPGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (E)-(S)-5-hydroxy-1-methyl-dec-6-enyl ester 在 三乙烯二胺 、 咪唑 、 titanium(IV) isopropylate 、 sodium periodate 、 potassium dioxotetrahydroxoosmate(VI) 、 potassium carbonate 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 63.5h， 生成 2,2-Dimethyl-propionic acid (5S,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-1-methyl-octyl ester
  参考文献：
  名称：

  Catalytic asymmetric synthesis of protected α-hydroxy aldehydes and related 1,2-difunctional chiral building blocks. An enantioselective synthesis of (−)-exo- and (−)-endo-brevicomin

  摘要：

  Chiral allylic alcohols which were prepared by the addition of functionalized dialkylzincs to alpha,beta-unsaturated aldehydes in good to excellent enantioselectivity, were converted to protected alpha-hydroxy aldehydes and 1,2-amino alcohols without loss of enantiomeric purity. Syn- or anti-1,2-diols can be obtained stereoselectively by a second asymmetric addition to alpha-silyloxy aldehydes. Functionalized 1,2-diols prepared in this way were converted to enantiomerically pure (-)-exo- and (-)-endo-brevicomin (>99% ee). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00036-0
• 作为产物：
  描述：

  2-已烯醛 、 di(4-pivaloxypentyl)zinc 在 titanium(IV) isopropylate 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 作用下， 生成 2,2-Dimethyl-propionic acid (E)-(S)-5-hydroxy-1-methyl-dec-6-enyl ester 、 2,2-Dimethyl-propionic acid (E)-(R)-5-hydroxy-1-methyl-dec-6-enyl ester
  参考文献：
  名称：

  Catalytic asymmetric synthesis of protected α-hydroxy aldehydes and related 1,2-difunctional chiral building blocks. An enantioselective synthesis of (−)-exo- and (−)-endo-brevicomin

  摘要：

  Chiral allylic alcohols which were prepared by the addition of functionalized dialkylzincs to alpha,beta-unsaturated aldehydes in good to excellent enantioselectivity, were converted to protected alpha-hydroxy aldehydes and 1,2-amino alcohols without loss of enantiomeric purity. Syn- or anti-1,2-diols can be obtained stereoselectively by a second asymmetric addition to alpha-silyloxy aldehydes. Functionalized 1,2-diols prepared in this way were converted to enantiomerically pure (-)-exo- and (-)-endo-brevicomin (>99% ee). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00036-0