(2R)-羟基(4-异丙基苯基)乙腈 | 121985-97-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2R)-羟基(4-异丙基苯基)乙腈
• 英文名称: 4-isopropyl-α-hydroxyphenylacetonitrile
• 英文别名: Benzeneacetonitrile, alpha-hydroxy-4-(1-methylethyl)-, (alphaR)-(9CI)；(2R)-2-hydroxy-2-(4-propan-2-ylphenyl)acetonitrile
• CAS: 121985-97-5
• 化学式: C₁₁H₁₃NO
• 分子量: 175.23
• InChiKey: FLXIHTKCTUICKQ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(6-甲氧基-2-萘基)丙酰氯 、 (2R)-羟基(4-异丙基苯基)乙腈 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  (S)-Naproxen® as a derivatizing agent to determine enantiomeric excess of cyanohydrins by HPLC

  摘要：

  An easy, inexpensive and accurate method to determine enantiomeric excess of cyanohydrins is described. The method consists in derivatization of cyanohydrins with (S)-naproxen(R) chloride and the products analyzed by HPLC. The results of enantiomeric excess so determined are similar to those obtained with [Eu(hfc)(3)], as a chiral shift reagent, and analysis by H-1-NMR of the cyanohydrins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01990-x
• 作为产物：
  描述：

  氢氰酸 、 4-异丙基苯甲醛 在 tartrate buffer 作用下， 以 异丙醚 为溶剂， 反应 336.0h， 生成 (-)-4-isopropyl-α-hydroxyphenylacetonitrile 、 (2R)-羟基(4-异丙基苯基)乙腈
  参考文献：
  名称：

  Novel (R)-oxynitrilase sources for the synthesis of (R)-cyanohydrins in diisopropyl ether

  摘要：

  Apple, apricot, cherry and plum meal were prepared from the seeds or kernels of mature garden fruits. The preparations as well as almond meal were used as the source of (R)-oxynitrilase for the synthesis of aliphatic and aromatic cyanohydrins in diisopropyl ether in the presence of 0.1 M tartrate buffer [2% (v/v), pH 5.4]. Apple meal as the most favourable of the enzyme preparations accepts also sterically hindered aldehydes (e.g., pivalaldehyde) as substrates, leading to (R)-cyanohydrins with high enantiopurity (usually ee>90%). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00080-3

文献信息

• (R)- and (S)-cyanohydrins using oxynitrilases in whole cells
  作者：Eero Kiljunen、Liisa T Kanerva

  DOI：10.1016/0957-4166(96)00116-4

  日期：1996.4

  Almond meal and Sorghum bicolor shoots were used as the sources of oxynitrilases for the preparation of a number (R)- and (S)-arylcyanohydrins, respectively, from the corresponding aldehydes in diisopropyl ether. Two different in situ methods were used to introduce hydrogen cyanide into the reaction mixture. In method 1, acetone cyanohydrin decomposes enzymatically and/or chemically to hydrogen cyanide

  杏仁粉和高粱双色芽被用作氧硝化酶的来源，分别从二异丙基醚中的相应醛中制备许多（R）-和（S）-芳基氰醇。使用两种不同的原位方法将氰化氢引入反应混合物中。在方法1中，丙酮氰醇通过酶和/或化学方式分解为氰化氢。在方法2中，氰化氢从二异丙醚中的溶液从反应容器的一个腔室中自由蒸发，最终到达另一个溶解在反应混合物中的区域。
• Tertiary Pentyl Groups Enhance Salen Titanium Catalyst for Highly Enantioselective Trimethylsilylcyanation of Aldehydes
  作者：Sidney Liang、Xiu R. Bu

  DOI：10.1021/jo0161779

  日期：2002.4.1

  recognized to be highly effective steric groups that can enhance enantioselectivity of salen titanium complexes when they are used in asymmetrical cyanation of aromatic aldehydes. High ee (92-97%) has been obtained with several aldehyde substrates. Compared to its tert-butyl analogue, the tert-pentyl group has been found to improve enantioselectivity and in some cases quite dramatically.

  叔戊基被认为是高效的立体基团，当它们用于芳族醛的不对称氰化时，可以提高salen钛配合物的对映选择性。使用几种醛底物已获得高 ee (92-97%)。与其叔丁基类似物相比，已发现叔戊基可提高对映选择性，并且在某些情况下相当显着。
• MATTHEWS, BARRY R.;JACKSON, W. ROY;JAYATILAKE, GAMINI S.;WILSHIRE, COLIN;+, AUSTRAL. J. CHEM., 41,(1988) N1, C. 1697-1709
  作者：MATTHEWS, BARRY R.、JACKSON, W. ROY、JAYATILAKE, GAMINI S.、WILSHIRE, COLIN、+

  DOI：——

  日期：——
• Novel (R)-oxynitrilase sources for the synthesis of (R)-cyanohydrins in diisopropyl ether
  作者：Eero Kiljunen、Liisa T. Kanerva

  DOI：10.1016/s0957-4166(97)00080-3

  日期：1997.4

  Apple, apricot, cherry and plum meal were prepared from the seeds or kernels of mature garden fruits. The preparations as well as almond meal were used as the source of (R)-oxynitrilase for the synthesis of aliphatic and aromatic cyanohydrins in diisopropyl ether in the presence of 0.1 M tartrate buffer [2% (v/v), pH 5.4]. Apple meal as the most favourable of the enzyme preparations accepts also sterically hindered aldehydes (e.g., pivalaldehyde) as substrates, leading to (R)-cyanohydrins with high enantiopurity (usually ee>90%). (C) 1997 Elsevier Science Ltd.
• (S)-Naproxen® as a derivatizing agent to determine enantiomeric excess of cyanohydrins by HPLC
  作者：Aida Soli´s、He´ctor Luna、Herminia I. Pe´rez、Norberto Manjarrez、Remedios Sa´nchez、Atilano Gutie´rrez

  DOI：10.1016/s0040-4039(98)01990-x

  日期：1998.11

  An easy, inexpensive and accurate method to determine enantiomeric excess of cyanohydrins is described. The method consists in derivatization of cyanohydrins with (S)-naproxen(R) chloride and the products analyzed by HPLC. The results of enantiomeric excess so determined are similar to those obtained with [Eu(hfc)(3)], as a chiral shift reagent, and analysis by H-1-NMR of the cyanohydrins. (C) 1998 Elsevier Science Ltd. All rights reserved.