rac-2-methyl-3-phenyl-1,2-propanediol | 90926-14-0

• 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: rac-2-methyl-3-phenyl-1,2-propanediol
• 英文别名: 2-methyl-3-phenylpropane-1,2-diol；(+/-)-2-methyl-3-phenyl-propane-1,2-diol；(+/-)-2-Methyl-3-phenyl-propan-1,2-diol
• CAS: 90926-14-0
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: ORQHQQLUNAKOKO-UHFFFAOYSA-N

物化性质

• 熔点：
  55-56 °C(Solv: ethyl ether (60-29-7); cyclohexane (110-82-7))
• 沸点：
  319.8±22.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  rac-2-methyl-3-phenyl-1,2-propanediol 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成 (3S)-3-hydroxy-3-methyl-4-phenylbutanenitrile
  参考文献：
  名称：

  An Efficient Large-Scale Synthesis of (R)-(-)-Mevalonolactone Using Simple Biological and Chemical Catalysts

  摘要：

  DOI：

  10.1055/s-1998-6108
• 作为产物：
  描述：

  (R,S)-2-hydroxy-2-methyl-3-phenylpropanoic acid 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 rac-2-methyl-3-phenyl-1,2-propanediol
  参考文献：
  名称：

  Davies et al., Journal of the Chemical Society, 1957, p. 3154,3156

  摘要：

  DOI：

文献信息

• S _N 2 Reactions at Tertiary Carbon Centers in Epoxides
  作者：Yong‐Qiang Zhang、Christina Poppel、Anastasia Panfilova、Fabian Bohle、Stefan Grimme、Andreas Gansäuer

  DOI：10.1002/anie.201702882

  日期：2017.8.7

  Described herein is a novel concept for SN2 reactions at tertiary carbon centers in epoxides without activation of the leaving group. Quantum chemical calculations show why SN2 reactions at tertiary carbon centers are proceeding in these systems. The reaction allows flexible synthesis of 1,3‐diol building blocks for natural product synthesis with excellent control of the relative and absolute configurations

  本文描述了在环氧化物中叔碳中心处的S N 2反应而不活化离去基团的新颖概念。量子化学计算表明为什么在这些系统中三级碳中心的S N 2反应正在进行。该反应可以灵活地合成1,3-二醇结构单元，用于天然产物的合成，并具有相对和绝对构型的出色控制。
• Palladium on Charcoal Catalyzed 3,4-Hydroperoxidation of α-Substituted Enals with Triethylsilane and Water
  作者：Petri Pihko、Sakari Tuokko

  DOI：10.1055/s-0035-1561633

  日期：——

  α-substituted acroleins with triethylsilane and water under Pd/C catalysis and aerobic conditions. The reaction is composed of a Pd/C-catalyzed conjugate reduction step and a hydroperoxidation step. The hydroperoxidation takes place via autoxidation of sufficiently stable enols formed in situ by transfer hydrogenation. Upon reduction, 2,2-disubstituted 1,2-diols are obtained directly from aldehydes.

  在 Pd/C 催化和有氧条件下，可以从 α-取代的丙烯醛与三乙基硅烷和水获得醛 α-氢过氧化物。该反应由 Pd/C 催化的共轭还原步骤和氢过氧化步骤组成。氢过氧化通过转移氢化原位形成的足够稳定的烯醇的自动氧化而发生。还原后，直接从醛得到 2,2-二取代的 1,2-二醇。
• 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。
• Recyclable Polyurea-Microencapsulated Pd(0) Nanoparticles:  An Efficient Catalyst for Hydrogenolysis of Epoxides
  作者：Steven V. Ley、Claire Mitchell、David Pears、Chandrashekar Ramarao、Jin-Quan Yu、Wuzong Zhou

  DOI：10.1021/ol0358509

  日期：2003.11.1

  Pd nanoparticles (similar to2 nm in size) microencapsulated in polyurea is an efficient and recyclable catalyst for reductive ring-opening hydrogenolysis of epoxides, using either HCOOH/Et3N or H-2 as a hydrogen donor.
• Biocatalytic resolution of 2-methyl-2-(aryl)alkyloxiranes using novel bacterial epoxide hydrolases
  作者：I. Osprian、W. Kroutil、M. Mischitz、K. Faber

  DOI：10.1016/s0957-4166(96)00493-4

  日期：1997.1

  Biocatalytic resolution of alkyl- and (arylalkyl)-oxiranes was accomplished by employing the epoxide hydrolase activity of lyophilized whole cells of seven bacterial strains belonging to the genera Rhodococcus, Mycobacterium and Nocardia. Whereas no suitable biocatalyst was found for 1-octene oxide, excellent selectivities were obtained with 2-methyl-2-substituted epoxides bearing an alkyl- or (aryl)alkyl side chain. (C) 1997, Elsevier Science Ltd. All rights reserved.