(R)-(+)-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: (R)-(+)-1-Phenylethyl 2,2-dimethylpropionate
• 英文别名: 1-phenyl-1-ethanoyl pivalate；(R)-1-phenylethyl pivalate；1-phenylethyl pivaloate；[(1R)-1-phenylethyl] 2,2-dimethylpropanoate
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: QERXLNZNXUZOIV-SNVBAGLBSA-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 作用下， 反应 12.0h， 生成 (R)-(+)-1-Phenylethyl 2,2-dimethylpropionate 、 (S)-(-)-1-Phenylethyl 2,2-dimethylpropionate
  参考文献：
  名称：

  Hammerschmidt, Friedrich; Hanninger, Achim, Chemische Berichte, 1995, vol. 128, # 11, p. 1069 - 1078

  摘要：

  DOI：

文献信息

• The effect of the migrating group structure on enantioselectivity in lipase-catalyzed kinetic resolution of 1-phenylethanol
  作者：Nedjma Melais、Louisa Aribi-Zouioueche、Olivier Riant

  DOI：10.1016/j.crci.2016.05.002

  日期：2016.8

  Abstract We have studied the effects of the acyl moiety on the enantioselectivity of three lipases: Candida antarctica B, Pseudomonas cepacia and Candida cylindracea, frequently used in kinetic resolutions by acylation or hydrolysis. The size of the acyl group was examined using various enol esters during the transesterification of 1-phenylethanol and the hydrolysis of the corresponding phenylethylesters

  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。
• 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.
• Lipase-mediated enantioselective acylation of alcohols with functionalized vinyl esters: acyl donor tolerance and applications
  作者：Robert Chênevert、Nicholas Pelchat、Pierre Morin

  DOI：10.1016/j.tetasy.2009.03.027

  日期：2009.6

  Enzymatic acylation is commonly used for the kinetic resolution of alcohols and amines. The simple acyl group introduced during the enzymatic reaction is Usually removed or replaced by another group. Retention of more complex acyl moieties as part of the target structures would be a more efficient strategy. We have studied the enantioselective acylation of a model alcohol substrate, 1-phenylethanol, with vinyl esters bearing various functionality on the acyl moieties in the presence of three lipases (Candida antarctica, Candida rugosa and Burkholderia cepacia) frequently used in organic synthesis. C. antarctica lipase is the most versatile lipase for this type of biotransformations. We applied this strategy to the synthesis of a protein kinase C ligand and a natural product, phoracantholide. (C) 2009 Elsevier Ltd. All rights reserved.
• 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.