(R)-(+)-1-(3'-chlorophenyl)propyl acetate | 497165-73-8

• 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: (R)-(+)-1-(3'-chlorophenyl)propyl acetate
• 英文别名: [(1R)-1-(3-chlorophenyl)propyl] acetate
• CAS: 497165-73-8
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: PYTRSKKYZITAFL-LLVKDONJSA-N

物化性质

• 沸点：
  258.2±15.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-(3'-chlorophenyl)propyl acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以94%的产率得到(R)-1-(3-chlorophenyl)propan-1-ol
  参考文献：
  名称：

  Biocatalytically assisted preparation of antifungal chlorophenylpropanols

  摘要：

  Fermenting baker's yeast converts 4'-chloropropiophenone 1 and 3'-chloropropiophenone 2 into enantiopure (S)-(-)-1(4'-chlorophenyl)propan-1-ol (S)-3 and (S)-(+)-1-(3'-chlorophenyl)propan-1-ol (S)-4, respectively. Application of inhibitors and organic solvents as additives enhanced the enantiomeric excesses. Enantiopure compounds (R)-(+)-1-(4'-chlorophenyl)propan-1-of ((R)-3) and (R)-(+)-1-(3'-chlorophenyl)propan-1-ol (R)-4 were prepared by lipase-mediated esterifications of the racemic alcohols. Maximum inhibition of the growth of the phytopathougenic fungus Botrytis cinerea was shown for the (R)-enantiomers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00415-9
• 作为产物：
  描述：

  在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 氢气 、 C₄₇H₄₁FeNO₂P₂ 作用下， 以 1,2-二氯乙烷 、 叔丁醇 为溶剂， 20.0 ℃ 、2.0 MPa 条件下， 反应 24.0h， 以88%的产率得到
  参考文献：
  名称：

  具有手性二茂铁基膦-亚磷酰胺配体的Rh催化α-芳基-β-烷基乙烯基酯的不对称加氢

  摘要：

  已经公开了三取代乙烯基酯的E / Z混合物的对映选择性Rh催化的氢化。以[Rh（COD）2 ] BF 4和结构上微调的手性二茂铁基膦-亚磷酰胺配体作为催化剂的组合，已成功地将各种α-芳基-β-烷基乙烯基酯的E / Z混合物加氢收率高，对映选择性好（至ee高达96％）。少量t BuOH的存在被证明对改善氢化结果有利。

  DOI：

  10.1016/j.tetlet.2020.152763

文献信息

• Rh-catalyzed asymmetric hydrogenation of α-aryl-β-alkylvinyl esters with chiral ferrocenylphosphine-phosphoramidite ligand
  作者：Chao Dong、Dao-Sheng Liu、Lei Zhang、Xiang-Ping Hu

  DOI：10.1016/j.tetlet.2020.152763

  日期：2021.2

  An enantioselective Rh-catalyzed hydrogenation of E/Z mixtures of trisubstituted vinyl esters has been disclosed. With a combination of [Rh(COD)2]BF4 and a structurally fine-tuning chiral ferrocenylphosphine-phosphoramidite ligand as the catalyst, a variety of E/Z mixtures of α-aryl-β-alkylvinyl esters have been successfully hydrogenated in high yields and with good to high enantioselectivities (up

  已经公开了三取代乙烯基酯的E / Z混合物的对映选择性Rh催化的氢化。以[Rh（COD）2 ] BF 4和结构上微调的手性二茂铁基膦-亚磷酰胺配体作为催化剂的组合，已成功地将各种α-芳基-β-烷基乙烯基酯的E / Z混合物加氢收率高，对映选择性好（至ee高达96％）。少量t BuOH的存在被证明对改善氢化结果有利。
• Biocatalytically assisted preparation of antifungal chlorophenylpropanols
  作者：Antonio J. Bustillo、Josefina Aleu、Rosario Hernández-Galán、Isidro G. Collado

  DOI：10.1016/s0957-4166(02)00415-9

  日期：2002.8

  Fermenting baker's yeast converts 4'-chloropropiophenone 1 and 3'-chloropropiophenone 2 into enantiopure (S)-(-)-1(4'-chlorophenyl)propan-1-ol (S)-3 and (S)-(+)-1-(3'-chlorophenyl)propan-1-ol (S)-4, respectively. Application of inhibitors and organic solvents as additives enhanced the enantiomeric excesses. Enantiopure compounds (R)-(+)-1-(4'-chlorophenyl)propan-1-of ((R)-3) and (R)-(+)-1-(3'-chlorophenyl)propan-1-ol (R)-4 were prepared by lipase-mediated esterifications of the racemic alcohols. Maximum inhibition of the growth of the phytopathougenic fungus Botrytis cinerea was shown for the (R)-enantiomers. (C) 2002 Elsevier Science Ltd. All rights reserved.