3-甲氧基-2-苯基-2-(三甲基硅氧基)丙腈 | 137057-20-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲氧基-2-苯基-2-(三甲基硅氧基)丙腈
• 英文名称: 3-methoxy-2-phenyl-2-(trimethylsilyloxy)propionitrile
• 英文别名: 3-Methoxy-2-phenyl-2-trimethylsilyloxypropanenitrile
• CAS: 137057-20-6
• 化学式: C₁₃H₁₉NO₂Si
• 分子量: 249.385
• InChiKey: AHHAKNKXRXPTEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-甲氧基-2-苯基-2-(三甲基硅氧基)丙腈 在 盐酸 、 氢氧化钾 、 三氟甲磺酸酐 、 溶剂黄146 作用下， 反应 86.0h， 生成 ethyl α-hydroxy-α-(methoxymethyl)-α-phenylacetate
  参考文献：
  名称：

  Synthesis and muscarinic cholinergic receptor affinities of 3-quinuclidinyl .alpha.-(alkoxyalkyl)-.alpha.-aryl-.alpha.-hydroxyacetates

  摘要：

  Seven analogues of 3-quinuclidinyl benzilate (QNB) in which one phenyl ring was replaced by an alkoxyalkyl moiety were synthesized and their affinities for the muscarinic cholinergic receptor determined. An oxygen in the beta-position of the moiety was not well-tolerated. By contrast, an oxygen in the gamma-position did not change the affinity for the muscarinic receptor. However, when a bromine was placed on the remaining phenyl ring, the affinity was significantly reduced in striking contrast to results obtained on halogenation of QNB.

  DOI：

  10.1021/jm00114a006
• 作为产物：
  描述：

  三甲基氰硅烷 、 2-甲氧基苯乙酮 在 indium(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到3-甲氧基-2-苯基-2-(三甲基硅氧基)丙腈
  参考文献：
  名称：

  由 InBr3 介导的将三甲基甲硅烷基氰化物加成到官能化酮中的便捷催化方法 - 深入了解反应机理

  摘要：

  本文描述了一种有用且实用的方法，用于在催化量的无水 InBr3 存在下将三甲基氰化硅烷 (TMSCN) 添加到多种官能化和未官能化的酮中。最佳程序涉及低催化剂负载（1 mol %），并且在芳香族和脂肪族酮的范围和适用性上似乎很普遍。所需的氰醇通常以 O-甲硅烷基醚的形式分离，化学产率良好至极好（高达 99%）。动力学和光谱研究表明，催化活性二聚铟物种参与反应机制。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200210)2002:19<3243::aid-ejoc3243>3.0.co;2-e

文献信息

• Indium tribromide: a highly effective catalyst for the addition of trimethylsilyl cyanide to α-hetero-substituted ketones
  作者：Marco Bandini、Pier Giorgio Cozzi、Paolo Melchiorre、Achille Umani-Ronchi

  DOI：10.1016/s0040-4039(01)00368-9

  日期：2001.4

  The catalytic addition of trimethylsilyl cyanide (TMSCN) to a large variety of hetero-substituted ketones promoted by anhydrous InBr3 has been studied. The low catalytic loading (0.1-1 mol%) and the mild experimental conditions required represent the key features of this novel catalytic system. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A Convenient Catalytic Procedure for the Addition of Trimethylsilyl Cyanide to Functionalised Ketones, Mediated by InBr3 − Insight into the Reaction Mechanism
  作者：Marco Bandini、Pier Giorgio Cozzi、Andrea Garelli、Paolo Melchiorre、Achille Umani-Ronchi

  DOI：10.1002/1099-0690(200210)2002:19<3243::aid-ejoc3243>3.0.co;2-e

  日期：2002.10

  This paper describes a useful and practical methodology for the addition of trimethylsilyl cyanide (TMSCN) to a large variety of functionalised and unfunctionalised ketones in the presence of catalytic amounts of anhydrous InBr3. The optimum procedure involves low catalyst loading (1 mol %) and appears general in scope and applicability for aromatic and aliphatic ketones. The desired cyanohydrins were

  本文描述了一种有用且实用的方法，用于在催化量的无水 InBr3 存在下将三甲基氰化硅烷 (TMSCN) 添加到多种官能化和未官能化的酮中。最佳程序涉及低催化剂负载（1 mol %），并且在芳香族和脂肪族酮的范围和适用性上似乎很普遍。所需的氰醇通常以 O-甲硅烷基醚的形式分离，化学产率良好至极好（高达 99%）。动力学和光谱研究表明，催化活性二聚铟物种参与反应机制。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Synthesis and muscarinic cholinergic receptor affinities of 3-quinuclidinyl .alpha.-(alkoxyalkyl)-.alpha.-aryl-.alpha.-hydroxyacetates
  作者：Victor I. Cohen、Raymond E. Gibson、Linda H. Fan、Rosanna De la Cruz、Miriam S. Gitler、Erin Hariman、Richard C. Reba

  DOI：10.1021/jm00114a006

  日期：1991.10

  Seven analogues of 3-quinuclidinyl benzilate (QNB) in which one phenyl ring was replaced by an alkoxyalkyl moiety were synthesized and their affinities for the muscarinic cholinergic receptor determined. An oxygen in the beta-position of the moiety was not well-tolerated. By contrast, an oxygen in the gamma-position did not change the affinity for the muscarinic receptor. However, when a bromine was placed on the remaining phenyl ring, the affinity was significantly reduced in striking contrast to results obtained on halogenation of QNB.