(2S)-2-(4-methoxyphenyl)-2-hydroxypropionitrile | 197579-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2S)-2-(4-methoxyphenyl)-2-hydroxypropionitrile
• 英文别名: (2S)-2-hydroxy-2-(4-methoxyphenyl)propanenitrile
• CAS: 197579-19-4
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: CJEDWUCDHJHJQD-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-(4-methoxyphenyl)-2-hydroxypropionitrile 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 [(1S)-1-cyano-1-(4-methoxyphenyl)ethyl] acetate
  参考文献：
  名称：

  Microbial-catalysed resolution of sterically demanding cyanohydrins

  摘要：

  Mycelia containing carboxyl-esterases, a novel source of enzymes, have been investigated in the hydrolytic kinetic resolution of one type of tert-alcohols, alpha,alpha-disubstituted cyanohydrins. This class of enzymes Was found to be both active and selective towards these tert-alcohols, giving E-values as high as 42. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2009.12.014
• 作为产物：
  描述：

  (S)-2-trimethylsilyloxy-2-(4'-methoxyphenyl)propanenitrile 在 盐酸 作用下， 以 水 为溶剂， 反应 16.0h， 生成 (2S)-2-(4-methoxyphenyl)-2-hydroxypropionitrile
  参考文献：
  名称：

  Microbial-catalysed resolution of sterically demanding cyanohydrins

  摘要：

  Mycelia containing carboxyl-esterases, a novel source of enzymes, have been investigated in the hydrolytic kinetic resolution of one type of tert-alcohols, alpha,alpha-disubstituted cyanohydrins. This class of enzymes Was found to be both active and selective towards these tert-alcohols, giving E-values as high as 42. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2009.12.014

文献信息

• Investigation of Lewis Acid versus Lewis Base Catalysis in Asymmetric Cyanohydrin Synthesis
  作者：Michael North、Marta Omedes-Pujol、Courtney Williamson

  DOI：10.1002/chem.201001078

  日期：——

  undertaken. When Lewis acid catalysis is dominant, a significantly positive reaction constant is observed, whereas reactions dominated by Lewis base catalysis give much smaller reaction constants. [Ti(salen)O}2] was found to show the highest degree of Lewis acid catalysis, whereas two [VO(salen)X] (X=EtOSO3 or NCS) complexes both displayed lower degrees of Lewis acid catalysis. In the case of reactions

  可以通过路易斯酸和/或路易斯碱催化三甲基甲硅烷基氰化物向醛的不对称加成，所述路易斯酸和/或路易斯碱分别活化所述醛和三甲基甲硅烷基氰化物。从催化剂的结构并不总是显而易见的是路易斯酸或路易斯碱催化是占主导地位。为了在使用钛，钒和铝的塞伦络合物作为催化剂的背景下进行研究，进行了不对称氰醇合成的哈米特分析。当路易斯酸催化起主导作用时，观察到明显的正反应常数，而路易斯碱催化占主导的反应给出的反应常数小得多。发现[Ti（salen）O} 2 ]显示出最高的路易斯酸催化程度，而两个[VO（salen）X]（X = EtOSO 3或NCS）配合物均显示较低程度的路易斯酸催化作用。在[Al（salen）} 2 O]和三苯膦氧化物催化的反应情况下，观察到非线性哈米特图，这表明随着羰基化合物变得更多电子，机理随着路易斯碱催化作用的增加而改变。 -不足。这些结果表明，铝络合物/三苯基膦氧化物催化剂体系也应催化
• Hydrolase-Catalysed Preparation of Chiral α,α-Disubstituted Cyanohydrin Acetates
  作者：Jarle Holt、Isabel W. C. E. Arends、Adriaan J. Minnaard、Ulf Hanefeld

  DOI：10.1002/adsc.200700053

  日期：2007.6.4

  The enzymatic hydrolysis of esters of tertiary alcohols has long been a challenge. In particular their kinetic resolutions have virtually not been addressed. Here we describe the successful kinetic resolution of α,α-disubstituted cyanohydrin acetates, a type of protected tertiary alcohols that form particularly interesting building blocks in organic synthesis. Utilising Subtilisin A the hydrolysis reaction

  叔醇酯的酶促水解长期以来一直是一个挑战。尤其是它们的动力学分辨率实际上还未得到解决。在这里，我们描述了α，α-二取代的氰醇乙酸盐的成功动力学拆分，这是一种受保护的叔醇，在有机合成中形成特别有趣的结构单元。利用枯草杆菌蛋白酶A，水解反应是（S）-选择性的，而皱纹念珠菌脂肪酶是（R）-选择性的。利用这些可商购的酶，现在可以得到α，α-二取代的氰醇乙酸盐的两种对映体。
• Microbial-catalysed resolution of sterically demanding cyanohydrins
  作者：Monica Paravidino、Jarle Holt、Diego Romano、Neetu Singh、Isabel W.C.E. Arends、Adriaan J. Minnaard、Romano V.A. Orru、Francesco Molinari、Ulf Hanefeld

  DOI：10.1016/j.molcatb.2009.12.014

  日期：2010.4

  Mycelia containing carboxyl-esterases, a novel source of enzymes, have been investigated in the hydrolytic kinetic resolution of one type of tert-alcohols, alpha,alpha-disubstituted cyanohydrins. This class of enzymes Was found to be both active and selective towards these tert-alcohols, giving E-values as high as 42. (C) 2009 Elsevier B.V. All rights reserved.