(S)-(-)-1-Phenylethyl 2,2-dimethylpropionate

• 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: (S)-(-)-1-Phenylethyl 2,2-dimethylpropionate
• 英文别名: 1-phenyl-1-ethanoyl pivalate；1-phenylethyl pivaloate；[(1S)-1-phenylethyl] 2,2-dimethylpropanoate
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: QERXLNZNXUZOIV-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苏合香醇 、 三甲基乙酰氯 在 吡啶 、 Pseudomonas cepacia lipase 、 水 作用下， 以 乙醚 为溶剂， 反应 48.0h， 生成 (R)-(+)-1-苯基乙醇 、 (S)-(-)-1-Phenylethyl 2,2-dimethylpropionate
  参考文献：
  名称：

  迁移基团结构对脂肪酶催化动力学拆分 1-苯基乙醇对映选择性的影响

  摘要：

  摘要 我们研究了酰基部分对三种脂肪酶的对映选择性的影响：南极念珠菌 B、洋葱假单胞菌和圆柱念珠菌，常用于通过酰化或水解进行动力学拆分。在 1-苯基乙醇的酯交换和相应苯乙基酯的水解过程中，使用各种烯醇酯检测酰基的大小。C. antarctica-B 脂肪酶在 1-苯基乙醇与异丙烯基和乙酸乙烯酯、癸酸乙烯酯、月桂酸乙烯酯的酯交换中显示出最高的选择性（E > 200）。1-苯基-乙基-乙酸酯、癸酸酯和月桂酸酯也可以用 CAL-B 以高选择性 (E > 150) 水解。结果可以与每种脂肪酶的三维形式相关联。

  DOI：

  10.1016/j.crci.2016.05.002

文献信息

• METHODS OF MAKING EFAVIRENZ AND INTERMEDIATES THEREOF
  申请人：CHEN Bo

  公开号：US20110015189A1

  公开（公告）日：2011-01-20

  The present invention provides a process for the preparation of Efavirenz. A compound of Formula 1 may be prepared by a process comprising cyclizing, in the presence of a first base, a compound of Formula 5 with a haloformate of Formula 6. Other processes are also provided as well as novel compounds prepared by and used in such processes.

  本发明提供了一种埃法韦伦的制备方法。通过在第一碱的存在下，将化合物5与化合物6的卤甲酸酯进行环化反应，可以制备出式1的化合物。还提供了其他制备方法，以及由这些方法制备和使用的新化合物。
• METHODS OF MAKING EFAVIRENS AND INTERMEDIATES THEREOF
  申请人：CHEN Bo

  公开号：US20120095249A1

  公开（公告）日：2012-04-19

  The present invention provides a process for the preparation of Efavirenz. A compound of Formula 1: may be prepared by a process comprising cyclizing, in the presence of a first base, a compound of Formula 5 with a haloformate of Formula 6. Other processes are also provided as well as novel compounds prepared by and used in such processes.

  本发明提供了一种制备埃法韦仑的方法。公式1的化合物可以通过在第一碱存在下，将公式5的化合物与公式6的卤仿酸酯环化而制备。还提供了其他方法以及由这些方法制备和使用的新化合物。
• Enantioselective Acylation of Secondary Alcohols Catalyzed by Chiral <i>N</i>-Heterocyclic Carbenes
  作者：Taichi Kano、Kouji Sasaki、Keiji Maruoka

  DOI：10.1021/ol050174r

  日期：2005.3.1

  The synthetic utility of chiral N-heterocyclic carbenes, which have been used mainly in transition metal-catalyzed reactions as a ligand, was demonstrated by the enantioselective acylation of secondary alcohols.
• Hammerschmidt, Friedrich; Hanninger, Achim, Chemische Berichte, 1995, vol. 128, # 11, p. 1069 - 1078
  作者：Hammerschmidt, Friedrich、Hanninger, Achim

  DOI：——

  日期：——
• Asymmetric Acylation of <i>s</i><i>ec</i>-Alcohols with Twisted Amides Possessing Axial Chirality Induced by the Adjacent Asymmetric Center
  作者：Shinji Yamada、Hiroko Katsumata

  DOI：10.1021/jo990892p

  日期：1999.12.1

  This paper reports that axially chiral twisted amides serve as asymmetric acylating agents for sec-alcohols under neutral conditions. Kinetic resolution of various racemic sec-alcohols and desymmetrization of 1,2-, 1,3-, and 1,4-meso-diols were performed by using the twisted amides. The utility of this desymmetrization method was shown by the preparation of the synthetic intermediate 28 for macrolide antibiotic nodusmicin and 18-deoxynargenicin. The stereoselectivity of the acylation reactions is significantly dependent on the bulkiness of both the acyl group and the C-4 substituent of the chiral auxiliary. When an amide possessing an imidazolyl group at C-4 was employed, the stereoselectivity was reversed to give R esters. A possible working model of the acylation reaction is also described on the basis of the structural studies of the twisted amides by IR and H-1 and C-13 NMR spectroscopies and AM1 calculations. These studies suggested that rotamer II is thermodynamically more stable than the others. The rotamer II has an axial chirality about its C(O)-N linkage that is induced by the adjacent chiral center. This would enable discrimination of the two enantiomeric hydroxy groups of the racemic alcohols or meso-diols.