(6S)-(+)-methyl 6,8-bis(4-nitrobenzoxy)octanoate | 168416-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6S)-(+)-methyl 6,8-bis(4-nitrobenzoxy)octanoate
• 英文别名: Octanoic acid, 6,8-bis[(4-nitrobenzoyl)oxy]-, methyl ester, (S)-；[(3S)-8-methoxy-3-(4-nitrobenzoyl)oxy-8-oxooctyl] 4-nitrobenzoate
• CAS: 168416-68-0
• 化学式: C₂₃H₂₄N₂O₁₀
• 分子量: 488.451
• InChiKey: ZOQQRRJKOSBHTG-FQEVSTJZSA-N

物化性质

• 沸点：
  632.5±55.0 °C(Predicted)
• 密度：
  1.322±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  171
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (6S)-(+)-methyl 6,8-bis(4-nitrobenzoxy)octanoate 在 sodium sulfide 、 氢氧化钾 、 potassium carbonate 、 sulfur 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.92h， 生成 R-(+)-硫辛酸
  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：

  (7R)-(-)-7-(2'-acetoxyethyl)-2-oxepanone 在 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (6S)-(+)-methyl 6,8-bis(4-nitrobenzoxy)octanoate
  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

• Application of enzymic Baeyer–Villiger oxidations of 2-substituted cycloalkanones to the total synthesis of (R)-(+)-lipoic acid
  作者：Brian Adger、M. Teresa Bes、Gideon Grogan、Ray McCague、Sandrine Pedragosa-Moreau、Stanley M. Roberts、Raffaella Villa、Peter W. H. Wan、Andew J. Willetts

  DOI：10.1039/c39950001563

  日期：——

  Oxidation of ketones 1a–h using a monooxygenase from Pseudomonas putida NCIMB 10007 gave the lactones 2a–h in optically active form: lactone 2h was converted into (R)-(+)-lipoic acid 9.

  使用来自假单胞菌Pseudomonas putida NCIMB 10007的单氧化酶对酮类化合物1a–h进行氧化，得到了光学活性的内酯2a–h：内酯2h被转化为(R)-(+)-α-硫辛酸9。
• The synthesis of (R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step
  作者：Brian Adger、M.Teresa Bes、Gideon Grogan、Raymond McCague、Sandrine Pedragosa-Moreau、Stanley M. Roberts、Raffaella Villa、Peter W.H. Wan、Andrew J. Willets

  DOI：10.1016/s0968-0896(96)00234-9

  日期：1997.2

  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.