(R)-1-(2',4'-dichlorophenyl)propan-1-ol

• 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-(2',4'-dichlorophenyl)propan-1-ol
• 英文别名: (R)-1-(2,4-dichlorophenyl)propan-1-ol；1-(2,4-dichlorophenyl)propan-1-ol；(1R)-1-(2,4-dichlorophenyl)propan-1-ol
• 化学式: C₉H₁₀Cl₂O
• 分子量: 205.084
• InChiKey: ZWTXYZVEHXCHFQ-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 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

• 作为产物：
  描述：

  2,4-二氯苯丙酮 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 四丁基溴化铵 、 水 、 sodium formate 、 (2S)-N-((R)-1-phenylethyl)pyrrolidine-2-carboxamide 作用下， 反应 36.0h， 生成 (R)-1-(2',4'-dichlorophenyl)propan-1-ol 、 (S)-1-(2',4'-dichlorophenyl)propan-1-ol
  参考文献：
  名称：

  手性氨基酰胺用于钌（II）催化酮在水中的不对称转移加氢反应

  摘要：

  手性氨基酰胺3衍生自L-脯氨酸，用于[RuCl 2（p- cymene）] 2催化的前手性酮在水中的不对称转移氢化。在存在2 mol％TBAB（n- Bu 4 NBr）作为相转移催化剂的情况下，获得了中度到良好的化学选择性（最高95％的收率）和对映选择性（最高90％ee）。《手性》，2010年。©2009 Wiley-Liss，Inc.。

  DOI：

  10.1002/chir.20723

文献信息

• Synthesis and application of 3-substituted (S)-BINOL as chiral ligands for the asymmetric ethylation of aldehydes
  作者：Zhi-Guang Zhang、Zhi-Bing Dong、Jin-Shan Li

  DOI：10.1002/chir.20842

  日期：2010.10

  A series of (S)‐BINOL ligands substituted at the 3 position with some five‐membered nitrogen‐containing aromatic heterocycles were effectively prepared and their catalytic abilities were evaluated in the asymmetric addition of diethylzinc to benzaldehyde in the presence of titanium tetraisopropoxide. Under the optimized reaction conditions, titanium complex of (S)‐3‐(1H‐benzimidazol‐1‐yl)‐1,1′‐bi‐2‐naphthol

  有效地制备了在3位上被五元含氮芳族杂环取代的一系列（S）-BINOL配体，并在四异丙醇钛存在下将二乙基锌不对称加成到苯甲醛中，评估了它们的催化能力。在优化的反应条件下，发现（S）-3-（1 H-苯并咪唑-1-基）-1,1'-联-2-萘酚的钛配合物是各种醛不对称乙基化的最有效催化剂以高达99％的收率和91％的ee生成相应的仲醇。手性，2010年。©2010 Wiley-Liss，Inc.。
• A systematic study of chiral homoprolinols and their derivatives in the catalysis of enantioselective addition of diethylzinc to aldehydes
  作者：Chang-Lu Liu、Chang-Yong Wei、Shi-Wen Wang、Yun-Gui Peng

  DOI：10.1002/chir.21017

  日期：2011.11

  active γ‐amino alcohols, were examined systematically in the enantioselective addition reactions of diethylzinc to aldehydes. By comparison of the results catalyzed by these γ‐amino alcohols with those by the β‐amino alcohols based on pyrrolidine architecture reported in the literature references, we have observed that the γ‐amino alcohols are superior to the corresponding β‐amino alcohols when the

  在二乙基锌与醛的对映选择性加成反应中，系统地检测了高脯氨醇类似物（一类旋光性γ-氨基醇）。通过比较文献参考文献报道的这些γ-氨基醇与基于吡咯烷结构的β-氨基醇催化的结果，我们观察到，当氮和氧未被取代。在我们测试的高脯酚中，2b在加成反应中获得最佳结果（45-88％收率，44-81％ee）。据我们所知，2b被认为是基于吡咯烷骨架的最有效的γ-氨基醇催化剂之一。手性，2011年。©2011 Wiley‐Liss，Inc.。
• Vasicine as tridentate ligand for enantioselective addition of diethylzinc to aldehydes
  作者：Mushtaq A. Aga、Brijesh Kumar、Abdul Rouf、Bhahwal A. Shah、Subhash C. Taneja

  DOI：10.1016/j.tetlet.2014.03.002

  日期：2014.4

  report of natural l-vasicine as tridentate chiral ligand for the enantioselective addition of diethylzinc to a variety of aliphatic and aromatic aldehydes is described. The ligand generates R-isomer of the secondary alcohols upto 98% ee. The quinazoline structure possibly imparts rigidity to the ligand and hence, consistently high enantioselectivity. The importance of the quinazoline ring was also supported

  描述了天然1- vasicine作为三齿手性配体用于将二乙基锌对映选择地添加到各种脂族和芳族醛中的第一个报道。所述配体产生仲醇的R-异构体，其高达98％ee。喹唑啉结构可能赋予配体刚性，因此，始终如一的高对映选择性。与其他相关配体的反应（部分缺乏结构特征）也支持了喹唑啉环的重要性，从而导致较差的对映选择性。
• L-Proline-Derived Tertiary Amino Alcohols as Chiral Ligands for Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Zhou Xu、Rongcheng Bo、Nan Wu、Yu Wan、Hui Wu

  DOI：10.2174/157017811797249380

  日期：2011.10.1

  series of L-proline derived tertiary amino alcohols was used as chiral ligands in the asymmetric addition reaction of Et2Zn to aldehydes. Among these ligands, it was found that ligand 1b which has the biggest steric and electrondonating substituent at the nitrogen position yielded the highest enantioselectivities when applied in the catalytic asymmetric addition of diethylzinc to p-chlorobenzadehyde

  在Et2Zn与醛的不对称加成反应中，一系列L-脯氨酸衍生的叔氨基醇被用作手性配体。在这些配体中，发现当将二乙基锌催化不对称加成到对氯苯并乙醛中时，在氮位置具有最大的空间和给电子取代基的配体1b产生最高的对映选择性。本文的实验结果可能会提供有益的经验，以帮助揭示配体结构和产品的ee值之间的关系。
• Asymmetric reduction of halo-substituted arylalkanones with Rhizopus arrhizus
  作者：Neeta A. Salvi、Subrata Chattopadhyay

  DOI：10.1016/j.tetasy.2008.07.035

  日期：2008.8

  The Rhizopus arrhizus-mediated asymmetric reduction of various haloaryl alkanones furnished the respective (S)-carbinols with good to excellent enantioselectivities. it was found that the reaction course was primarily governed by the relative position of the halogen with respect to the carbonyl group. and its size. The relative order of efficacies of the nature of the halogen and their substitution pattern were Br > Cl > F and o- > p- > m-. The ortho-effect was the most predominant factor in the stereochemical outcome of the reaction, which was also confirmed with some non-halo-substituted acetophenones. (C) 2008 Elsevier Ltd. All rights reserved.