(R)-1-acetoxy-1-phenylethanol | 258523-87-4

• 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: (R)-1-acetoxy-1-phenylethanol
• 英文别名: [(1R)-2-hydroxy-1-phenylethyl] acetate
• CAS: 258523-87-4
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: LOLNQOPVHRAGHR-JTQLQIEISA-N

物化性质

• 沸点：
  306.3±22.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-1-acetoxy-1-phenylethanol 在 Amberlite IRA-401 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (S)-1-acetoxy-1-phenylethanol
  参考文献：
  名称：

  Preparation of the enantiomers of 1-phenylethan-1,2-diol. Regio- and enantioselectivity of acylase I and Candida antarctica lipases A and B

  摘要：

  Acylase 1 and Cundida antarctica lipases A (CAL-A) and B (CAL-B) were evaluated for the preparation of the enantiomers of 1-phenylethan-1,2-diol. In the presence of CAL-B, the sequential one-pot methanolysis of the diacetate in acetonitrile allowed the preparation of (S)-diol (e.e. 97%) and (R)-1-acetoxy-1-phenylethanol (e.e. 94%). Base-catalyzed methanolysis of the monoacetate resulted in the corresponding (R)-diol. When one of the diol enantiomers wets subjected to Mitsunobu esterification, inversion of configuration occurred, allowing transformation of the initially racemic mixture to one enantiomer. Acylase 1-catalysis led to the chemo- and enantioselective formation of (S)-1-acetoxy-1-phenylethanol (e.e. 97%) in the presence of the primary hydroxyl function through acetylation of the secondary hydroxyl group. The low chemical yield (ca. 25%) was due to the moderate enzymatic regioselectivity. CAL-A behaved in a similar way to acylase 1. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00428-1
• 作为产物：
  描述：

  1-苯基-1,2-乙二醇二乙酸盐 在 Candida antarctica lipase B 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 110.0h， 生成 (R)-1-acetoxy-1-phenylethanol
  参考文献：
  名称：

  Preparation of the enantiomers of 1-phenylethan-1,2-diol. Regio- and enantioselectivity of acylase I and Candida antarctica lipases A and B

  摘要：

  Acylase 1 and Cundida antarctica lipases A (CAL-A) and B (CAL-B) were evaluated for the preparation of the enantiomers of 1-phenylethan-1,2-diol. In the presence of CAL-B, the sequential one-pot methanolysis of the diacetate in acetonitrile allowed the preparation of (S)-diol (e.e. 97%) and (R)-1-acetoxy-1-phenylethanol (e.e. 94%). Base-catalyzed methanolysis of the monoacetate resulted in the corresponding (R)-diol. When one of the diol enantiomers wets subjected to Mitsunobu esterification, inversion of configuration occurred, allowing transformation of the initially racemic mixture to one enantiomer. Acylase 1-catalysis led to the chemo- and enantioselective formation of (S)-1-acetoxy-1-phenylethanol (e.e. 97%) in the presence of the primary hydroxyl function through acetylation of the secondary hydroxyl group. The low chemical yield (ca. 25%) was due to the moderate enzymatic regioselectivity. CAL-A behaved in a similar way to acylase 1. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00428-1

文献信息

• Challenging the absence of observable hydrogens in the assignment of absolute configurations by NMR: application to chiral primary alcohols
  作者：Félix Freire、José Manuel Seco、Emilio Quiñoá、Ricardo Riguera

  DOI：10.1039/b617184b

  日期：——

  The absolute configuration of beta-chiral primary alcohols devoid of observable hydrogens on one of the beta-substituents at the asymmetric carbon (L(1)/L(2)) can be determined by comparison of the (1)H NMR of their (R)- and (S)-9-AMA ester derivatives and analysis of the Deltadelta(RS) for the L substituent and the Cbeta-H.

  β-手性伯醇的绝对构型在不对称碳（L（1）/ L（2））的β-取代基之一上没有可观察到的氢，可以通过比较它们的（1）H NMR来确定R）-和（S）-9-AMA酯衍生物以及L取代基和Cbeta-H的Deltadelta（RS）分析。
• Enantioselective production of (S)-1-phenyl-1,2-ethanediol from dicarboxyesters by recombinant Bacillus subtilis esterase
  作者：Xin Tian、Gao-Wei Zheng、Chun-Xiu Li、Zhi-Long Wang、Jian-He Xu

  DOI：10.1016/j.molcatb.2011.07.022

  日期：2011.12

  The whole cells of recombinant Escherichia coli BL21 overexpressing a Bacillus subtilis esterase (BsE) were utilized to sequentially hydrolyze the dicarboxyester of 1-phenyl-1,2-ethanediol for production of (S)-1-phenyl-1.2-ethanediol (PED), exhibiting high hydrolytic activity, excellent regio- and enantioselectivities towards the dicarboxyester of PED. Among the dicarboxyesters with different acyl chains (e.g., acetyl, n-butyl, and n-hexyl), the best enantioselectivity (E=176) was observed when PED diacetate was employed as the initial substrate. Various reaction conditions were systematically investigated for enantioselective hydrolysis of PED diacetate. Under the optimal reaction conditions, kinetic resolution of 100 mM PED diacetate resulted in 49% conversion within 1 h, affording (S)-PED in 96% ee. A 150-ml scale reaction was performed, affording (S)-PED in 49% yield and 95% ee. After recrystallization in chloroform, the optical purity of (S)-PED was improved up to >99% ee, with a total yield of 45%. These results imply that this recombinant esterase (BsE) is a potentially promising biocatalyst for bioproduction of (S)-PED, an important chiral building block with wide application in pharmaceutical industry and liquid-crystal display materials. (C) 2011 Elsevier B.V. All rights reserved.