(+)-(1S,2S)-1-phenyl-1-chloro-2-propanol | 160332-15-0

• 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: (+)-(1S,2S)-1-phenyl-1-chloro-2-propanol
• 英文别名: (1S,2S)-1-chloro-1-phenyl-2-propanol；(1S,2S)-1-chloro-1-phenylpropan-2-ol
• CAS: 160332-15-0
• 化学式: C₉H₁₁ClO
• 分子量: 170.639
• InChiKey: LQRBZMKDUZCVAI-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-(1S,2S)-1-phenyl-1-chloro-2-propanol 在 sodium ethanolate 作用下， 以 甲醇 为溶剂， 以60%的产率得到(2S,3R)-2-methyl-3-phenyloxirane
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane

  摘要：

  All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane (beta-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described(1) and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.

  DOI：

  10.1016/0957-4166(94)80167-3
• 作为产物：
  描述：

  苯基丙酮 在 磺酰氯 作用下， 以 四氯化碳 为溶剂， 反应 24.0h， 生成 (+)-(1S,2S)-1-phenyl-1-chloro-2-propanol
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane

  摘要：

  All the stereoisomers of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane (beta-methylstyrene oxide) have been prepared in three steps from 4-phenyl-2-butanone and 1-phenyl-2-propanone or 1-phenyl-1-propanone respectively. The key step is the microbiological reduction of the corresponding haloketones. These results confirm those previously described(1) and demonstrate that the chemoenzymatic synthesis of homochiral 2,3-epoxides is a general method that can be used whatever the starting ketone.

  DOI：

  10.1016/0957-4166(94)80167-3

文献信息

• Selective manganese-mediated transformations using the combination:
  作者：István E Markó、Paul R. Richardson、Mark Bailey、Anita R. Maguire、Niall Coughlan

  DOI：10.1016/s0040-4039(97)00309-2

  日期：1997.3

  A novel manganese reagent, generated from KMnO4 and Me3SiCl, in the presence of a quaternary ammonium salt, is shown to smoothly dichlorinate alkenes, open epoxides and chemoselectively oxidise sulfides to sulfoxides.

  一种新型的锰试剂，由KMnO 4和Me 3 SiCl生成，在季铵盐的存在下，可以平稳地将烯烃二氯化，形成开放的环氧化物，并化学选择性地将硫化物氧化为亚砜。
• Non-Racemic Halohydrinsvia Biocatalytic Hydrogen-Transfer Reduction of Halo-Ketones and One-Pot Cascade Reaction to Enantiopure Epoxides
  作者：Tina M. Poessl、Birgit Kosjek、Ursula Ellmer、Christian C. Gruber、Klaus Edegger、Kurt Faber、Petra Hildebrandt、Uwe T. Bornscheuer、Wolfgang Kroutil

  DOI：10.1002/adsc.200505094

  日期：2005.11

  possibility for a follow-up reaction of halohydrins is the ring closure to the corresponding epoxide. A novel “one pot-one step strategy” was employed to obtain the enantiopure epoxide from the α-chloro-ketone in a cascade like fashion at pH>12 involving biocatalytic hydrogen transfer reduction and in situ chemo-catalyzed ring closure.

  通过使用红球菌作为冻干细胞催化剂或得自荧光假单胞菌DSM 50106（PF-ADH）的醇脱氢酶制剂，α-氯酮的生物催化氢转移还原可提供非外消旋的氯醇。对于所研究的所有底物，红球菌均严格提供“ Prelog”产品，而PF-ADH显示出分散的立体偏好。卤代醇的后续反应的一种可能性是与相应的环氧化物的闭环。一种新颖的“一站式一步策略”被用于从α-氯代酮中以级联方式在pH> 12的条件下获得对映纯的环氧化物，包括生物催化的氢转移还原和原位化学催化的闭环反应。