1-acetoxy-2-(1,4-dioxa-spiro[4.5]dec-6-yl)-ethane | 93043-74-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-acetoxy-2-(1,4-dioxa-spiro[4.5]dec-6-yl)-ethane
• 英文别名: 1-Acetoxy-2-(1,4-dioxa-spiro[4.5]dec-6-yl)-aethan；1-Acetoxy-2-(2,2-aethylendioxy-cyclohexyl)-aethan；2-(1,4-Dioxaspiro[4.5]decan-6-yl)ethyl acetate
• CAS: 93043-74-4
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: FUTHHFSGKMOBFA-UHFFFAOYSA-N

物化性质

• 沸点：
  152 °C(Press: 13 Torr)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-acetoxy-2-(1,4-dioxa-spiro[4.5]dec-6-yl)-ethane 在 盐酸 、 cyclopentanone monooxygenase 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 甲醇 为溶剂， 反应 1.75h， 生成 (2R)-(-)-2-(2'-acetoxyethyl)cyclohexanone
  参考文献：
  名称：

  The synthesis of (R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step

  摘要：

  2-(2-Acetoxyethyl)cyclohexanone (4) was converted into the lactone (-)-(5) regio- and enantioselectively using 2-oxo-Delta(3)-4,5,5-trimethylcyclopentenyl acetyl-CoA monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from camphor grown Pseudomonas putida NCIMB 10007. The lactone (-)-(5) was converted into (R)-(+)-lipoic acid in six steps. In contrast cyclopentanone monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from cyclopentanol-grown Pseudomonas sp. NCIMB 9872 selectively oxidized the (S)-enantiomer of the ketone (4) giving better access to optically enriched, naturally occurring lipoic acid. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00234-9
• 作为产物：
  描述：

  (1,4-dioxaspiro[4.5]dec-6-yl)acetic acid ethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 1-acetoxy-2-(1,4-dioxa-spiro[4.5]dec-6-yl)-ethane
  参考文献：
  名称：

  The synthesis of (R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step

  摘要：

  2-(2-Acetoxyethyl)cyclohexanone (4) was converted into the lactone (-)-(5) regio- and enantioselectively using 2-oxo-Delta(3)-4,5,5-trimethylcyclopentenyl acetyl-CoA monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from camphor grown Pseudomonas putida NCIMB 10007. The lactone (-)-(5) was converted into (R)-(+)-lipoic acid in six steps. In contrast cyclopentanone monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from cyclopentanol-grown Pseudomonas sp. NCIMB 9872 selectively oxidized the (S)-enantiomer of the ketone (4) giving better access to optically enriched, naturally occurring lipoic acid. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00234-9

文献信息

• A New Synthesis of 6-Thioctic Acid (DL-α-Lipoic Acid)
  作者：Augusto Segre、René Viterbo、Giovanni Parisi

  DOI：10.1021/ja01570a054

  日期：1957.7
• Segre et al.
  作者：Segre et al.

  DOI：——

  日期：——