(S)-1-(2-氯苯基)丙烷-1-醇 | 158635-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-1-(2-氯苯基)丙烷-1-醇
• 英文名称: (S)-1-(2-chlorophenyl)propanol
• 英文别名: (S)-1-(2-chloro-phenyl)-propan-1-ol；(1S)-1-(2-chlorophenyl)propan-1-ol；(S)-1-(2'-chlorophenyl)-1-propanol；(S)-1-(2'-chlorophenyl)propan-1-ol；(S)-1-(2-chlorophenyl)-1-propanol；(S)-1-(2-chlorophenyl)propan-1-ol
• CAS: 158635-38-2
• 化学式: C₉H₁₁ClO
• 分子量: 170.639
• InChiKey: UBOFXBQTRQSKMY-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：

  (+)-MTPA chloride 、 (S)-1-(2-氯苯基)丙烷-1-醇 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Asymmetric reduction of halo-substituted arylalkanones with Rhizopus arrhizus

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2008.07.035
• 作为产物：
  描述：

  2-氯苯丙酮 在 Rhizopus arrhizus 作用下， 以 乙醇 为溶剂， 反应 192.0h， 以62%的产率得到(S)-1-(2-氯苯基)丙烷-1-醇
  参考文献：
  名称：

  Asymmetric reduction of halo-substituted arylalkanones with Rhizopus arrhizus

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2008.07.035

文献信息

• Dual Stereoselectivity in the Dialkylzinc Reaction Using (−)-β-Pinene Derived Amino Alcohol Chiral Auxiliaries
  作者：Caitlin M. Binder、April Bautista、Marek Zaidlewicz、Marek P. Krzemiński、Allen Oliver、Bakthan Singaram

  DOI：10.1021/jo802371z

  日期：2009.3.20

  morpholino group through a simple substitution reaction. 3-MAP was characterized by X-ray crystallography, which displayed the rigidity of the pinane framework. Amino alcohol 2-MAP was prepared from its trans isomer 2, which in turn was synthesized via hydroboration/oxidation of the morpholine enamine of (+)-nopinone. Two-dimensional NMR was used to characterize amino alcohol 2-MAP, and NOE was used to confirm

  由天然存在的（-）-β-pine烯制备的（+）-诺品酮以非常好的收率和出色的异构体纯度转化为两种区域异构的氨基醇3-MAP和2-MAP。通过将（+）-壬基酮转化为相应的α-酮肟，合成了氨基醇3-MAP。将其还原为伯氨基醇，并通过简单的取代反应将其转化为吗啉代基团。通过X射线晶体学表征了3-MAP，其显示了ane烷骨架的刚性。氨基醇2-MAP由其反式异构体2制备依次通过（+）-诺哌酮的吗啉烯胺的硼氢化/氧化反应合成。使用二维NMR表征氨基醇2-MAP，并使用NOE确认其相对立体化学。这些氨基醇被用作手性助剂，向苯甲醛中添加了二乙基锌，以在产物中获得接近定量的不对称诱导。使用3-MAP可在99％ee中产生（S）-苯基丙醇，其区域异构体2-MAP也可在99％ee中得到相反的对映异构体，（R）-苯基丙醇。其他芳族，脂族和α，β-不饱和醛也用这种方法实施，从而以高收率和对映体过量提供仲醇。氨基醇还发
• Switching of Enantioselectivity in the Catalytic Addition of Diethylzinc to Aldehydes by Regioisomeric Chiral 1,3-Amino Sulfonamide Ligands
  作者：Takuji Hirose、Kazuyuki Sugawara、Koichi Kodama

  DOI：10.1021/jo200834n

  日期：2011.7.1

  Twenty chiral 1,3-amino sulfonamides of two classes (2a–i and 3a–k) have been prepared from (−)-cis-2-benzamidocyclohexanecarboxylic acid (1) and studied as ligands for catalytic enantioselective addition of Et2Zn to a variety of aromatic and aliphatic aldehydes. The ligands 2 and 3 are regioisomers in which the position of the amine and sulfonamide groups is exchanged. Each class of ligands with the

  从（-）-顺式-2-苯甲酰胺基环己烷羧酸（1）制备了两类（2a – i和3a – k）的二十种手性1,3-氨基磺酰胺，并研究了其作为Et 2 Zn催化对映选择性加成的配体。各种芳香族和脂肪族醛。配体2和3是区域异构体，其中胺和磺酰胺基团的位置被交换。显示具有相同手性的每一类配体提供具有相反立体化学的仲醇。结构调查表明，叔氨基和p的组合-甲苯磺酰脲基对反应最有效。通过优化结构和反应条件，最佳配体定量提供了两种对映体仲醇，对（S）-和（R）-对映体的对映体选择性良好，对映体选择性分别高达94％和98％ee 。
• d-Penicillamine and l-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols
  作者：M. Elisa Silva Serra、Dora Costa、Dina Murtinho、Nélia C.T. Tavares、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.tet.2016.08.036

  日期：2016.9

  d-Penicillamine derived thiazolidine ligands were prepared in a two-step synthetic sequence and used in the enantioselective alkylation of a variety of aromatic aldehydes with diethylzinc at room temperature. Excellent ee, up to >99%, and nearly complete conversions were observed. Structurally analogous l-cysteine derived thiazolidine ligands were also synthesized and tested for comparative purposes

  d-青霉胺衍生的噻唑烷配体以两步合成顺序制备，并在室温下用于各种芳香醛与二乙基锌的对映选择性烷基化。优秀的ee，高达> 99％，并且观察到几乎完全的转换。还合成了结构相似的1-半胱氨酸衍生的噻唑烷配体，并进行了比较试验，结果显示出很好的选择性，尽管选择性略低，最高可达89％。两种噻唑烷的组合使用构成合成（S）和（R）手性仲醇的对映异构体，从而引出了无数有用的具有相反绝对构型的旋光产物。
• Synthesis of Chiral Pyridylphenols for the Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Pei-Shan Wu、Chinpiao Chen

  DOI：10.1002/jccs.201100474

  日期：2012.6

  Chiral 8‐substituted 2‐(8,10,10‐trimethyl‐6‐aza‐tricyclo[7.1.1.02,7]undeca‐2(7),3,5‐trien‐5‐yl)‐phenols were prepared from a high enantiopurity (>97% ee) of (1R)‐(+)‐α‐pinene, and assessed in the enantioselective addition of diethylzinc to substituted benzaldehydes, giving the (S)‐alcohols with enantiomeric excess ranging from 33% to 89%. Interestingly, in all cases, except for those of ortho‐chlorobenzaldehyde

  制备了手性8取代的2-（8,10,10-三甲基-6-氮杂-三环[7.1.1.0 2,7 ] undeca -2（7），3,5-三烯-5-基）酚（1 R）-（+）-α-pine烯的高对映体纯度（> 97％ee），并通过将二乙基锌对映体选择性添加到取代的苯甲醛中进行评估，得到的（S）-对映体过量度为33％至89％。有趣的是，在所有情况下，除邻氯苯甲醛，邻甲氧基和对甲氧基苯甲醛外，ee均> 71％。Hammett取代常数与二乙基锌添加到邻或对位的对映体过量的关系图预取代的苯甲醛呈线性关系。
• Noscapine Derivatives as New Chiral Catalysts in Asymmetric Synthesis­: Highly Enantioselective Addition of Diethylzinc to Aldehydes­
  作者：Peyman Salehi、Maryam Mohebbi、Morteza Bararjanian、Samad Ebrahimi、Martin Smieško

  DOI：10.1055/s-0037-1609224

  日期：2018.5

  chiral induction. The first examples of noscapinoid compounds as efficient catalysts in asymmetric synthesis are now reported. Three derivatives of noscapine were synthesized from its reaction with different Grignard reagents. Asymmetric addition of diethylzinc to aldehydes­ was performed in the presence of these catalysts in high yields and good to excellent ees. Noscapine, a natural alkaloid, has

  摘要 Noscapine，一种天然生物碱，从未用作手性诱导的母体支架。现在报道了类辣椒素化合物在不对称合成中作为有效催化剂的第一个例子。从其与不同的格氏试剂反应可合成出Noscapine的三种衍生物。在这些催化剂的存在下，二乙基锌与醛的不对称加成以高收率和良好至优异的ee进行。 Noscapine，一种天然生物碱，从未用作手性诱导的母体支架。现在报道了类辣椒素化合物在不对称合成中作为有效催化剂的第一个例子。从其与不同的格氏试剂反应可合成出Noscapine的三种衍生物。在这些催化剂的存在下，二乙基锌与醛的不对称加成以高收率和良好至优异的ee进行。