(1S,3S)-1-(4-chlorophenyl)-1,3-butanediol | 1204698-86-1

• 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,3S)-1-(4-chlorophenyl)-1,3-butanediol
• 英文别名: (1S,3S)-1-(4-chlorophenyl)-1,3-butandiol；1-(4-chlorophenyl)-1,3-butanediol；1-(4-chlorophenyl)butane-1,3-diol；(1S,3S)-1-(4-chlorophenyl)butane-1,3-diol
• CAS: 1204698-86-1
• 化学式: C₁₀H₁₃ClO₂
• 分子量: 200.665
• InChiKey: CGLAAYALTMIKPM-XVKPBYJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-4-hydroxy-4-(4-chlorophenyl)butan-2-one 在 异丙醇 、 还原型辅酶Ⅰ 作用下， 反应 24.0h， 生成 (1S,3S)-1-(4-chlorophenyl)-1,3-butanediol
  参考文献：
  名称：

  使用手性Zn2 +复合催化剂的对映体选择性Aldol反应单锅化学合成手性1,3-二元醇，并使用辅酶再生利用氧化还原酶进行酶还原

  摘要：

  我们以前报道于丙酮的对映选择性羟醛缩合反应和一些醛催化手性的Zn 2+的复合物大号脯氨酰基的侧[12] ANEN 4（大号-ZnL 1）和大号己酰基侧链[12] ANEN 4（大号-水溶液中的ZnL 2）。在这里，我们报道了在室温下，通过L-和D-苯丙氨酰侧基的Zn 2+配合物催化的对映选择性羟醛反应的组合，在水性溶剂体系中通过一锅化学酶法合成手性1,3-二醇。] aneN 4（L -ZnL3和D- ZnL 3）以及通过氧化还原酶的连续对映体选择性还原以及NADH（烟酰胺腺嘌呤二核苷酸的还原形式）辅因子的再生。研究结果表明，1,3-二醇所有四种立体异构体可通过手性的Zn的适当选择来制备2+ -配合物和商购自“Chiralscreen OH”试剂盒氧化还原酶。

  DOI：

  10.1002/asia.201100584

文献信息

• Catalytic 1,3-Difunctionalisation of Organic Backbones through a Highly Stereoselective, One-Pot, Boron Conjugate-Addition/Reduction/Oxidation Process
  作者：Cristina Solé、Amolak Tatla、Jose A. Mata、Andrew Whiting、Henrik Gulyás、Elena Fernández

  DOI：10.1002/chem.201102081

  日期：2011.12.9

  enantioselectivity provided by the CuI catalyst modified with Josiphos‐ and Mandyphos‐type ligands has been examined. The oxidative substitution of the boryl unit with a hydroxyl group proceeds with complete retention of configuration at the Cβ‐atom. In parallel, the stoichiometric reduction of the imino or carbonyl group provides a second stereogenic centre. Depending on the nature of the reducing reagent

  建立了简单的一锅三步合成路线，制备手性1,3-氨基醇和1,3-二醇。考虑到合成方案的整体立体控制，第一步和关键步骤分别是对映选择性的α，β-不饱和亚胺和酮的β-硼酸酯。研究了用Josiphos和Mandyphos型配体改性的Cu I催化剂提供的对映选择性。的甲硼烷基单元的氧化性取代与在C配置的完全保留的羟基进行β -原子。同时，亚氨基或羰基的化学计量还原提供了第二个立体定向中心。根据还原剂的性质，可以实现极高的非对映选择性，特别是对于合成试剂而言。-1,3-氨基醇和1,3-二醇
• Sequential and Modular Synthesis of Chiral 1,3-Diols with Two Stereogenic Centers: Access to All Four Stereoisomers by Combination of Organo- and Biocatalysis
  作者：Katrin Baer、Marina Kraußer、Edyta Burda、Werner Hummel、Albrecht Berkessel、Harald Gröger

  DOI：10.1002/anie.200900582

  日期：2009.11.23

  Biocompatible: A modular chemoenzymatic synthesis (see scheme) based on asymmetric organo‐ and biocatalytic reaction sequences allows the sequential construction of both stereogenic centers of 1,3‐diols and leads to all four possible stereoisomers in enantiomerically pure form. The biocompatibility of the organocatalytic aldol reaction allows its direct use in the subsequent enzymatic reduction without

  生物相容性：基于不对称有机和生物催化反应序列的模块化化学酶促合成（请参见方案）允许顺序构建1,3-二醇的两个立体异构中心，并导致对映体纯净形式的所有四种可能的立体异构体。有机催化醛醇缩合反应的生物相容性使其可以直接用于随后的酶促还原反应中，而无需进行后处理步骤。
• Exploring the potential of some yeast strains in the stereoselective synthesis of aldol reaction products and its reduced 1,3-dialcohol derivatives
  作者：Cecilia Andreu、Marcel·lí del Olmo

  DOI：10.1016/j.molcatb.2013.03.017

  日期：2013.8

  The behavior of two yeast strains has been studied under different conditions. Both microorganims catalyzed the aldol reaction between activated aldehydes and acetone when a large amount of the latter was present in the reaction medium producing, with moderate stereoselectivity, the aldol product with the R configuration. No reduction of any of the products present in the medium was detected. On the other hand, the carbonyl group of the racemic aldol was reduced to produce chiral 1,3-dialcohol derivatives when water was employed as the only solvent. In this case, the resolution of the racemic starting material was also possible with one of the biocatalysts, and the aldol was recovered with the S configuration. A complementary enantioselectivity was shown by both microorganisms in the generation of the new stereogenic center, which allowed access to 3 of the 4 possible diastereomeric diols with high enantiomerical purity. (C) 2013 Elsevier B.V. All rights reserved.
• One-pot Chemoenzymatic Synthesis of Chiral 1,3-Diols Using an Enantioselective Aldol Reaction with Chiral Zn2+ Complex Catalysts and Enzymatic Reduction Using Oxidoreductases with Cofactor Regeneration
  作者：Shotaro Sonoike、Toshinari Itakura、Masanori Kitamura、Shin Aoki

  DOI：10.1002/asia.201100584

  日期：2012.1.2

  reported on enantioselective aldol reactions of acetone and some aldehydes catalyzed by chiral Zn2+ complexes of L‐prolyl‐pendant [12]aneN4 (L‐ZnL1) and L‐valyl‐pendant [12]aneN4 (L‐ZnL2) in aqueous solution. Here, we report on the one‐pot chemoenzymatic synthesis of chiral 1,3‐diols in an aqueous solvent system at room temperature by a combination of enantioselective aldol reactions catalyzed by Zn2+ complexes

  我们以前报道于丙酮的对映选择性羟醛缩合反应和一些醛催化手性的Zn 2+的复合物大号脯氨酰基的侧[12] ANEN 4（大号-ZnL 1）和大号己酰基侧链[12] ANEN 4（大号-水溶液中的ZnL 2）。在这里，我们报道了在室温下，通过L-和D-苯丙氨酰侧基的Zn 2+配合物催化的对映选择性羟醛反应的组合，在水性溶剂体系中通过一锅化学酶法合成手性1,3-二醇。] aneN 4（L -ZnL3和D- ZnL 3）以及通过氧化还原酶的连续对映体选择性还原以及NADH（烟酰胺腺嘌呤二核苷酸的还原形式）辅因子的再生。研究结果表明，1,3-二醇所有四种立体异构体可通过手性的Zn的适当选择来制备2+ -配合物和商购自“Chiralscreen OH”试剂盒氧化还原酶。