(2S)-3-phenyl-propane-1,2-diol diacetate | 86551-93-1

• 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: (2S)-3-phenyl-propane-1,2-diol diacetate
• 英文别名: (S)-3-phenylpropane-1,2-diyl diacetate；(S)-1,2-diacetoxy-3-phenylpropane；[(2S)-2-acetyloxy-3-phenylpropyl] acetate
• CAS: 86551-93-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: WJXSVAKLHNEJSP-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S)-3-phenyl-propane-1,2-diol diacetate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (S)-(-)-3-phenyl-1,2-propanediol
  参考文献：
  名称：

  Sanghvi, Y. S.; Dabral, V.; Rao, A. S., Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983, vol. 22, # 1, p. 64

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(dimethyl-phenyl-silanyl)-3-phenyl-propionic acid 在 O-benzoylquinine 过氧乙酸 、 草酰氯 、 mercury(II) diacetate 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 (2S)-3-phenyl-propane-1,2-diol diacetate
  参考文献：
  名称：

  The highly enantioselective transformation of silylketenes into α-silylthioesters catalysed by cinchona alkaloids

  摘要：

  The reaction of silylketenes with thiophenol, mediated by cinchona alkaloid catalysts, proceeds to give alpha -silylthioester products in good chemical yield and with enantiomeric excess values in the range 79-93%. The absolute configuration of one of the thioester products was determined by X-ray diffraction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00304-5

文献信息

• Influence of α-methyl substitution of proline-based organocatalysts on the asymmetric α-oxidation of aldehydes
  作者：Sok-Teng (Amy) Tong、Margaret A. Brimble、David Barker

  DOI：10.1016/j.tet.2009.04.060

  日期：2009.6

  The direct asymmetric organocatalytic α-oxidation of aldehydes using trans-2-(p-methylphenylsulfonyl)-3-phenyloxaziridine is reported. This method affords the S isomer of α-hydroxy aldehydes, thereby complementing the selectivity for the R isomer observed using the two-step nitrosobenzene method. Use of α-methylproline and α-methylproline tetrazole significantly increases the enantioselectivity observed

  报道了使用反式2-（对甲基苯基磺酰基）-3-苯基恶二氮丙啶对醛的直接不对称有机催化α-氧化。该方法提供了α-羟基醛的S异构体，从而补充了使用两步亚硝基苯方法观察到的R异构体的选择性。与类似的未取代的有机催化剂相比，使用α-甲基脯氨酸和α-甲基脯氨酸四唑显着提高了醛的α-氧化观察到的对映选择性。
• Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation
  作者：Gabriella Egri、Eszter Baitz-Gács、László Poppe

  DOI：10.1016/0957-4166(96)00161-9

  日期：1996.5

  Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzyme and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions. Copyright (C) 1996 Elsevier Science Ltd
• SANGHVI, Y. S.;DABRAL, V.;RAO, A. S., INDIAN J. CHEM., 1983, 22, N 1, 64
  作者：SANGHVI, Y. S.、DABRAL, V.、RAO, A. S.

  DOI：——

  日期：——