α-acetoxy-2-(3,4-methylenedioxyphenyl)acetonitrile | 119798-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: α-acetoxy-2-(3,4-methylenedioxyphenyl)acetonitrile
• 英文别名: 1-cyano-1-[3,4-(methylenedioxy)phenyl]methyl acetate；acetoxy-benzo[1,3]dioxol-5-yl-acetonitrile；Acetoxy-benzo[1,3]dioxol-5-yl-acetonitril；[1,3-Benzodioxol-5-yl(cyano)methyl] acetate
• CAS: 119798-32-2
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: QLJQZNQAUINIDB-UHFFFAOYSA-N

物化性质

• 沸点：
  345.3±42.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-acetoxy-2-(3,4-methylenedioxyphenyl)acetonitrile 在 甲醇 、 钯 、 溶剂黄146 作用下， 生成 胡椒乙胺
  参考文献：
  名称：

  Kondo et al., Itsuu Kenkyusho Nempo, 1953, # 4, p. 20,29;engl.Ref.S.70

  摘要：

  DOI：
• 作为产物：
  描述：

  胡椒醛 在 四丁基溴化铵 、 sodium hydrogensulfite 作用下， 以 环己烷 、 水 为溶剂， 反应 1.5h， 生成 α-acetoxy-2-(3,4-methylenedioxyphenyl)acetonitrile
  参考文献：
  名称：

  A simple separation method for (S)-hydroxynitrile lyase from cassava and its application in asymmetric cyanohydrination

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2013.03.015

文献信息

• Zinc Tetrafluoroborate-Catalyzed Efficient Conversion of Aldehydes to Geminal Diacetates and Cyanoacetates
  作者：Brindaban C. Ranu、Jyotirmoy Dutta、Arijit Das

  DOI：10.1246/cl.2003.366

  日期：2003.4

  A trace of an aqueous solution of zinc tetrafluoroborate was demonstrated to catalyze the conversion of an aldehyde to its 1,1-diacetate by acetic anhydride without any solvent. A similar reaction of an aldehyde with a mixture of potassium cyanide and acetic anhydride in methylene chloride was also catalyzed by Zn(BF4)2 to provide the corresponding geminal cyanoacetate.

  演示了一种含锌四氟硼酸盐的水溶液在无任何溶剂的情况下催化醛向其1,1-二乙酸酯的转化，该转化是通过乙酸酐实现的。类似地，在二氯甲烷中，醛与氰化钾和乙酸酐的混合反应也受到Zn(BF₄)₂的催化，生成相应的乙二酸酯。
• Ionic Liquid [bmim]BF₄ as an Efficient and Recyclable Reaction Medium for the Synthesis of <i>O</i>-Acetyl Cyanohydrin via One-Pot Condensation of Aldehyde, TMSCN, and Ac₂O
  作者：Zhi-Liang Shen、Shun-Jun Ji

  DOI：10.1080/00397910802431172

  日期：2009.2.9

  Abstract Ionic liquid [bmim]BF4 has been demonstrated to be an efficient and environmentally friendly reaction medium as well as reaction promoter for the synthesis of O-acetyl cyanohydrin via one-pot condensation of aldehyde, TMSCN, and Ac2O without Lewis acid or any special activation. In addition, the recovered ionic liquid could be reused for subsequent runs without the loss of activity.

  摘要 离子液体 [bmim]BF4 已被证明是一种高效、环保的反应介质以及反应促进剂，用于通过醛、TMSCN 和 Ac2O 的一锅缩合合成 O-乙酰氰醇，无需路易斯酸或任何特殊的激活。此外，回收的离子液体可以重新用于后续运行而不会损失活性。
• Combination of the lipase-catalysed resolution with the Mitsunobu esterification in one pot
  作者：Eero Vänttinen、Liisa T Kanerva

  DOI：10.1016/0957-4166(95)00224-d

  日期：1995.7

  A chemo-enzymatic method for the preparation of homochiral esters of 14 secondary alcohols with 100% theoretical yields is described in one pot through two steps: the lipase-catalysed kinetic resolution followed by the Mitsunobu esterification of the free alcohol enantiomer in situ in the resolution mixture. Mathematical equations which link the enzymatic and chemical steps were derived, resulting in an enantioconvergent synthetic tool for the preparation of chiral intermediates.
• Albert, Chemische Berichte, 1915, vol. 48, p. 475,478
  作者：Albert

  DOI：——

  日期：——
• Über neue und über verbesserte Wege zum Aufbau von pharmakologisch wichtigen Aminen II. Über die Synthese von ß-Aryl-äthylaminen aus aromatischen Aldehyden und Carbonsäuren
  作者：Karl Kindler

  DOI：10.1002/ardp.19312690504

  日期：——