(R)-1-cyanobutyl acetate | 129313-21-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-1-cyanobutyl acetate
• 英文别名: 1-cyanobutyl acetate；[(1S)-1-cyanobutyl] acetate
• CAS: 129313-21-9
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: FRRYAKXYRWOFSR-ZETCQYMHSA-N

物化性质

• 沸点：
  212.9±13.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-羟基戊腈 以 吡啶 为溶剂， 反应 12.0h， 生成 (R)-1-cyanobutyl acetate
  参考文献：
  名称：

  Ohta, Hiromichi; Hiraga, Satoshi; Miyamoto, Kenji, Agricultural and Biological Chemistry, 1988, vol. 52, # 12, p. 3023 - 3028

  摘要：

  DOI：

文献信息

• Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes
  作者：Ewelina Błocka、Mariusz J. Bosiak、Mirosław Wełniak、Agnieszka Ludwiczak、Andrzej Wojtczak

  DOI：10.1016/j.tetasy.2014.03.001

  日期：2014.4

  Five tridentate Schiff bases have been prepared from (1R,2S,3R,4S)-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol and salicylaldehydes. X-ray structure investigation revealed differences in their molecular conformation, and their titanium(IV) complexes have been studied with NMR techniques. Among them the complex with the Schiff base obtained from 2-hydroxy-3-isopropylbenzaldehyde, is the most selective

  五三齿席夫碱已经从（1制备- [R，2小号，3 - [R，4小号）-3-氨基- 1,7,7-三甲基二环[2.2.1]庚-2-醇和水杨醛。X射线结构的调查显示在它们的分子构象的差异，和它们的钛（IV）络合物进行了研究NMR技术。它们之间的复合物与由2-羟基-3-异丙基苯甲醛得到的席夫碱，为脂肪族，脂环族，芳族，杂芳族和醛的硅氰化反应最有选择性的催化剂。最高的对映选择性，> 99％时，在加入三甲基氰硅烷的给肉桂醛实现。
• High-Throughput Preparation of Optically Active Cyanohydrins Mediated by Lipases
  作者：Juliana Christina Thomas、Bruno Bernardi Aggio、Alfredo Ricardo Marques de Oliveira、Leandro Piovan

  DOI：10.1002/ejoc.201601028

  日期：2016.12

  Cyanohydrins are versatile compounds with high applicability in organic synthesis; they are used as starting materials for the synthesis of other chemical targets with high industrial added value. Lipase-mediated kinetic resolution reactions are a promising route for the synthesis of optically active cyanohydrins. These reactions can be carried out through the acylation of cyanohydrins or the deacylation

  氰醇是一种用途广泛的化合物，在有机合成中具有很高的适用性；它们被用作合成其他具有高工业附加值的化学目标的起始材料。脂肪酶介导的动力学拆分反应是合成光学活性氰醇的一条有前途的途径。这些反应可以通过氰醇的酰化或氰醇酯的脱酰化，在不同的生物催化剂和不同的反应条件下进行。不幸的是，根据底物结构，可能需要较长的反应时间才能达到合适的对映体过量。在这种情况下，我们提出了一种以连续流模式生产光学活性氰醇的高通量协议。获得的产物具有中等至良好的对映选择性（E 值从 8 到 > 200) 并且连续流模式下的生产率值比批处理模式高 2.4 到 8.7 倍。此外，反应时间从分批模式下的数小时减少到连续流动模式下的数分钟。
• Method of preparing optically active cyanohydrin derivatives
  申请人：DUPHAR INTERNATIONAL RESEARCH B.V

  公开号：EP0601632A1

  公开（公告）日：1994-06-15

  The invention relates to a method of preparing an optically active cyanohydrin carboxylic acid ester from an optically active cyanohydrin of opposite configuration, wherein said starting cyanohydrin is converted with a carboxylic acid in the presence of a dialkyl azodicarboxylate and a triarylphosphine. The invention also relates to a method of preparing an optically active cyanohydrin of opposite configuration by a subsequent solvolysis of the ester obtained under conservation of the configuration.

  本发明涉及一种从构型相反的光学活性氰醇制备光学活性氰醇羧酸酯的方法，其中所述起始氰醇在偶氮二甲酸二烷基酯和三芳基膦存在下与羧酸进行转化。 本发明还涉及一种制备光学活性相反构型氰醇的方法，该方法是通过随后溶解在保持构型条件下获得的酯来制备光学活性相反构型的氰醇。
• Effenberger, Franz; Stelzer, Uwe, Chemische Berichte, 1993, vol. 126, # 3, p. 779 - 786
  作者：Effenberger, Franz、Stelzer, Uwe

  DOI：——

  日期：——
• A simple separation method for (S)-hydroxynitrile lyase from cassava and its application in asymmetric cyanohydrination
  作者：Zubiao Zheng、Yan Zi、Zhongzhou Li、Xinzhuo Zou

  DOI：10.1016/j.tetasy.2013.03.015

  日期：2013.4

  Using an acetone precipitation method, crude (S)-hydroxynitrile lyase [(S)-MeHNL] was separated from Munihot esculenta (cassava) leaves, and used directly as biocatalyst to catalyze asymmetric cyanohydrination and produce cyanohydrins with enantiomeric purities (>= 90% ee) significantly greater than those previously reported. The use of a water/i-Pr2O system with an enzyme, NaCN, and appropriate amounts of acetic acid is crucial in improving the stereoselectivity of cyanohydrin formation by minimizing the non-enzymatic reaction and the racemization of the chiral products. The proposed isolation method for crude (S)-MeHNL has a high value because of its simplicity, and low cost as well as the high activity of the crude (S)-MeHNL. (C) 2013 Elsevier Ltd. All rights reserved.