(-)-(1R,2R)-1-phenyl-2-chloro-1-propanol | 160332-19-4

• 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: (-)-(1R,2R)-1-phenyl-2-chloro-1-propanol
• 英文别名: 2-chloro-1-phenylpropanol；(1R,2R)-2-chloro-1-phenylpropan-1-ol
• CAS: 160332-19-4
• 化学式: C₉H₁₁ClO
• 分子量: 170.639
• InChiKey: UPFXSURABKQPFA-APPZFPTMSA-N

物化性质

• 沸点：
  263.1±20.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：

  (-)-(1R,2R)-1-phenyl-2-chloro-1-propanol 在 sodium ethanolate 作用下， 以 甲醇 为溶剂， 以70%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：

  2-氯苯丙酮 反应 48.0h， 生成 (-)-(1R,2S)-1-phenyl-2-chloro-1-propanol 、 (-)-(1R,2R)-1-phenyl-2-chloro-1-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

• Cross-Linked Artificial Enzyme Crystals as Heterogeneous Catalysts for Oxidation Reactions
  作者：Sarah Lopez、Laurianne Rondot、Chloé Leprêtre、Caroline Marchi-Delapierre、Stéphane Ménage、Christine Cavazza

  DOI：10.1021/jacs.7b09343

  日期：2017.12.13

  field of oxidation, remains a constraint for their increased use in the field. Here, thanks to the design of cross-linked artificial nonheme iron oxygenase crystals, we filled this gap by developing biobased heterogeneous catalysts capable of oxidizing carbon-carbon double bonds. First, reductive O2 activation induces selective oxidative cleavage, revealing the indestructible character of the solid catalyst

  设计融合多相催化、酶学和分子催化优势的系统代表了可持续化学的下一个主要目标。交联酶晶体显示了大部分这些基本资产（精心设计的介孔支持、蛋白质选择性和底物的分子识别）。然而，缺乏反应多样性，特别是在氧化领域，仍然限制了它们在该领域的应用增加。在这里，由于交联人工非血红素铁加氧酶晶体的设计，我们通过开发能够氧化碳碳双键的生物基多相催化剂填补了这一空白。首先，还原性 O2 激活诱导选择性氧化裂解，揭示了固体催化剂的坚不可摧的特性（至少 30 000 周转次数没有任何活性损失）。其次，使用 2 电子氧化剂可以实现具有数千个转换数的选择性和高效羟基氯化。迄今为止，这项新技术的性能远远优于单独使用无机复合物甚至溶液中的人工酶的催化作用。简单的催化剂合成、“组学”技术的改进和蛋白质结晶的自动化相结合，使这一策略成为（生物）催化未来的真正机会。甚至溶液中的人工酶。简单的催化剂合成、“组学”技术的改进和蛋白质
• Chemoenzymatic synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane
  作者：Pascale Besse、Michel F. Renard、Henri Veschambre

  DOI：10.1016/0957-4166(94)80167-3

  日期：1994.7

  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.