2-methyl-3-phenylpropane-1,2-diol | 159701-46-9

• 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: 2-methyl-3-phenylpropane-1,2-diol
• 英文别名: (S)-2-benzyl-1,2-propanediol；(S)-2-methyl-3-phenyl-propane-1,2-diol；(S)-2-Methyl-3-phenyl-propan-1,2-diol；(2S)-2-methyl-3-phenylpropane-1,2-diol
• CAS: 159701-46-9
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ORQHQQLUNAKOKO-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 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：

  rac-2-methyl-3-phenyl-1,2-propanediol 生成 2-methyl-3-phenylpropane-1,2-diol
  参考文献：
  名称：

  Enantioselective Pseudomonas fluorescens (P. cepacia) lipase-catalyzed irreversible transesterification of 2-methyl-1,2-diols in an organic solvent

  摘要：

  The Pseudomonas fluorescens (P. cepacia) lipase-catalyzed irreversible transesterification of 2-phenyl-1,2-propanediol 1a is not enantioselective, whereas the diols 1b and 1c are enzymatically resolved with the same procedure to (S)-1b and 1c (>98 and 92% e.e.) and the (R)-acetates 2b and 2c (92% e.e.).

  DOI：

  10.1016/s0957-4166(00)86267-9

文献信息

• Chiral Primary Amine Catalyzed Asymmetric Epoxidation of α-Substituted Acroleins
  作者：Jiuyuan Li、Niankai Fu、Long Zhang、Pengxin Zhou、Sanzhong Luo、Jin-Pei Cheng

  DOI：10.1002/ejoc.201001117

  日期：2010.12

  substrates in asymmetric epoxidation reactions. In this study, chiral primary amines are shown to catalyze the asymmetric epoxidation of α-substituted acroleins, a versatile type of 1,1-disubstituted terminal alkene. Among various chiral primary amines explored, the chiral primary-tertiary vicinal diamine derived from trans-1,2-diphenylethane-1,2-diamine is identified as the optimal catalyst, which, in combination

  1,1-二取代末端烯烃在不对称环氧化反应中仍然是具有挑战性的底物。在这项研究中，手性伯胺被证明可以催化 α-取代丙烯醛的不对称环氧化，这是一种多功能的 1,1-二取代末端烯烃。在探索的各种手性伯胺中，衍生自反式-1,2-二苯基乙烷-1,2-二胺的手性伯-叔邻二胺被确定为最佳催化剂，其与5-磺基水杨酸（5-SSA）结合使用, 表现出良好的催化活性（高达 95% 的产率）和对映选择性（高达 88% ee）。发现 2 M 氯化钠水溶液是最佳反应介质。
• Deracemization of (±)-2,2-disubstituted epoxides via enantioconvergent chemoenzymatic hydrolysis using Nocardia EH1 epoxide hydrolase and sulfuric acid
  作者：Romano V.A. Orru、Wolfgang Kroutil、Kurt Faber

  DOI：10.1016/s0040-4039(97)00201-3

  日期：1997.3

  2-Substituted (S)-1,2-diols were prepared in a one-pot procedure with >90% ee and >90% isolated yield via deracemization of (±)-2,2-disubstituted oxiranes through sequential (i) biocatalytic asymmetric hydrolysis using Nocardia EH1 epoxide hydrolase and (ii) acid catalyzed hydrolysis of the remaining oxirane enantiomer.

  一锅法制备2-取代的（S）-1,2-二醇，并通过顺序（i）生物催化对（±）-2,2-二取代的氧杂环己烷进行脱硫，从而获得> 90％ee和> 90％分离的收率使用诺卡氏菌EH1环氧水解酶进行不对称水解，以及（ii）酸催化剩余环氧乙烷对映体的水解。
• N-Boc 2-Acyloxazolidines: Useful precursors to enantiopure 1,2-diols via highly diastereoselective nucleophilic additions
  作者：Claude Agami、François Couty、Christelle Lequesne

  DOI：10.1016/0040-4020(95)00145-x

  日期：1995.4

  phenylglycinol. This preparation involves: (i) a transformation of the above β-amino alcohols into N-Boc 2-ethoxycarbonyloxazolidines, (ii) the formation of the corresponding Weinreb amides and, (iii) a reaction between these amides and organometallic reagents. Such diastereomerically pure heterocycles react cleanly with various nucleophilic reagents (Grinard reagents, sodium borohydride and allylsilane) to afford

  N -Boc 2-乙酰基恶唑烷是由去氧麻黄碱和苯基甘醇合成的。该制备涉及：（i）将上述β-氨基醇转化为N。-Boc 2-乙氧基羰基恶唑烷，（ii）形成相应的Weinreb酰胺，和（iii）这些酰胺与有机金属试剂之间的反应。这样的非对映异构纯杂环与各种亲核试剂（格林纳德试剂，硼氢化钠和烯丙基硅烷）干净地反应，得到相应的醇。用三氟乙酸处理这些羟基恶唑烷，然后水解和还原中间体α-羟基醛，得到1,2-二醇。在大多数情况下，整体转化表现出完全的非对映选择性，这可以由用于亲核加成的螯合模型来解释。
• Methods for Obtaining Optically Active Epoxides and Vicinal Diols From 2,2-Disubstituted Epoxides
  申请人：Botes Adriana Leonora

  公开号：US20080286832A1

  公开（公告）日：2008-11-20

  The invention provides yeast strains, and polypeptides encoded by genes of such yeast strains, that have enantiospecific 2,2-disubstituted epoxide hydrolase activity. The invention also features nucleic acid molecules encoding such polypeptides, vectors containing such nucleic acid molecules, and cells containing such vectors. Also embraced by the invention are methods for obtaining optically active 2,2-disubstituted vicinal diols and optically active 2,2-disubstituted epoxides.

  该发明提供了酵母菌株，以及这些酵母菌株基因编码的多肽，具有对映选择性的2,2-二取代环氧乙烷水解酶活性。该发明还涵盖编码这些多肽的核酸分子，包含这些核酸分子的载体以及含有这些载体的细胞。该发明还涵盖了获得光学活性2,2-二取代邻二醇和光学活性2,2-二取代环氧化物的方法。
• Phase-transfer catalyzed enantioselective α-alkylation of α-acyloxymalonates: construction of chiral α-hydroxy quaternary stereogenic centers
  作者：Min Woo Ha、Sujee Choi、Seek Kim、Jun Young Lee、Jae Kyun Lee、Jeeyeon Lee、Suckchang Hong、Hyeung-geun Park

  DOI：10.1039/c6ra15121c

  日期：——

  The enantioselective synthesis of α-acyloxy-α-alkylmalonates was developed as an efficient method for producing chiral α-tertiary alcohols, which are potentially valuable intermediates in the synthesis of natural products and pharmaceuticals. The efficient enantioselective α-alkylation of diphenylmethyl tert-butyl α-acyloxymalonates was accomplished via phase-transfer catalysis in the presence of (S

  开发α-酰氧基-α-烷基丙二酸酯的对映选择性合成是生产手性α-叔醇的有效方法，所述α-叔醇是天然产物和药物合成中潜在的有价值的中间体。在（S，S）-3,4,5-三氟苯基-NAS溴化物的存在下通过相转移催化完成对二苯基甲基叔丁基α-酰氧基丙二酸酯的有效对映选择性α-烷基化反应，得到相应的α-酰氧基-α -烷基丙二酸酯的化学收率高（高达99％）和光学收率（ee高达93％），可以很容易地转化为具有手性α-叔醇基团的通用手性中间体。