Chloro-acetic acid (S)-1-tert-butylsulfanylmethyl-heptyl ester | 145021-10-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Chloro-acetic acid (S)-1-tert-butylsulfanylmethyl-heptyl ester
• 英文别名: [(2S)-1-tert-butylsulfanyloctan-2-yl] 2-chloroacetate
• CAS: 145021-10-9
• 化学式: C₁₄H₂₇ClO₂S
• 分子量: 294.886
• InChiKey: RFUNQWDIAAVNHB-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid (S)-1-tert-butylsulfanylmethyl-heptyl ester 在 palladium on activated charcoal 、 Lindlar's catalyst 喹啉 、 sodium hydroxide 、 正丁基锂 、 三氟化硼乙醚 、 水 、 氢气 、 trimethoxonium tetrafluoroborate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 19.75h， 生成 (6S)-6-hexyltetrahydropyran-2-one
  参考文献：
  名称：

  Enzyme assisted synthesis of enantiomerically pure δ-lactones

  摘要：

  Both enantiomeric series of a wide variety of optically pure 6-alkylated delta-lactones - saturated as well as unsaturated - were prepared via an enzyme mediated route. The key reaction step is the nucleophilic ring opening of enantiomerically pure alkyl-oxiranes, accessible via the corresponding beta-hydroxythioethers which can be obtained enantiomerically pure via enzyme catalyzed kinetic resolutions.

  DOI：

  10.1016/s0957-4166(00)80146-9
• 作为产物：
  描述：

  1,2-环氧辛烷 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 生成 Chloro-acetic acid (S)-1-tert-butylsulfanylmethyl-heptyl ester
  参考文献：
  名称：

  Enzyme assisted synthesis of enantiomerically pure δ-lactones

  摘要：

  Both enantiomeric series of a wide variety of optically pure 6-alkylated delta-lactones - saturated as well as unsaturated - were prepared via an enzyme mediated route. The key reaction step is the nucleophilic ring opening of enantiomerically pure alkyl-oxiranes, accessible via the corresponding beta-hydroxythioethers which can be obtained enantiomerically pure via enzyme catalyzed kinetic resolutions.

  DOI：

  10.1016/s0957-4166(00)80146-9

文献信息

• Lipase catalyzed resolution of 1-t-butylthio-2-alkanols: Enzyme mediated routes to enantiomerically pure 1,2-epoxyalkanes and 2-alkanols
  作者：Ulrich Goergens、Manfred P. Schneider

  DOI：10.1016/s0957-4166(00)82099-6

  日期：1992.9

  A series of 1-t-butylthio-2-alkanols (R)- and (S)-1-5 were prepared via lipase catalyzed resolution of the corresponding chloroacetates (+/-)-1a-5a and further converted into the optically pure alkyloxiranes (R)-6-8 and 2-alkanols (R)-14-15
• Enzyme assisted synthesis of enantiomerically pure δ-lactones
  作者：Bernhard Haase、Manfred P. Schneider

  DOI：10.1016/s0957-4166(00)80146-9

  日期：1993.5

  Both enantiomeric series of a wide variety of optically pure 6-alkylated delta-lactones - saturated as well as unsaturated - were prepared via an enzyme mediated route. The key reaction step is the nucleophilic ring opening of enantiomerically pure alkyl-oxiranes, accessible via the corresponding beta-hydroxythioethers which can be obtained enantiomerically pure via enzyme catalyzed kinetic resolutions.