2-(氰基甲基)-3-苯基丙酸甲酯 | 170304-80-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-(氰基甲基)-3-苯基丙酸甲酯
• 英文名称: methyl 2-(cyanomethyl)-3-phenylpropanoate
• 英文别名: methyl 2-cyanomethyl-3-phenylpropanoate；Methyl 2-benzyl-3-cyanopropanoate
• CAS: 170304-80-0
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: KNSMFCYVNOCHDH-UHFFFAOYSA-N

物化性质

• 沸点：
  350.3±35.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(氰基甲基)-3-苯基丙酸甲酯 在 sodium tetrahydroborate 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 48.0h， 以56%的产率得到3-苄基吡咯烷-2-酮
  参考文献：
  名称：

  3,3-Dialkyl- and 3-Alkyl-3-Benzyl-Substituted 2-Pyrrolidinones:  A New Class of Anticonvulsant Agents

  摘要：

  A series of 3,3-dialkyl- and 3-alkyl-3-benzyl-substituted 2-pyrrolidinones (lactams) have been prepared and evaluated for their anticonvulsant activities. In the pentylenetetrazole mouse seizure model, 3,3-diethyl lactam 7c and 3-benzyl-3-ethyl lactam 7j are the most effective anticonvulsants (ED(50) = 46 and 42 mg/kg, respectively) and have protective index (PI = TD50/ED(50)) values of 5.65 and 3.00, respectively. These protective index values compare favorably to those of the clinically used antiepileptic drugs ethosuximide (ED(50) = 161 mg/kg), phenobarbital (ED(50) = 22 mg/kg), and valproic acid (ED(50) = 133 mg/kg), which have PI values of 2.35, 4.00, and 2.12, respectively. The benzyl compounds [3-substituents are Bn, H (7h); Bn, Me (7i); and Bn, Et (7j)] are also very effective anticonvulsants against seizures induced by maximal electroshock (ED(50) = 41, 55, and 74 mg/kg, respectively) and have PI values of 3.51, 3.04, and 1.70, respectively. The corresponding PI values for phenobarbital and valproic acid are 1.37 and 5.18, respectively. As a class of anticonvulsants, the 3,3-disubstituted 2-pyrrolidinones have a broad spectrum of action and may be useful for the treatment of human epilepsies.

  DOI：

  10.1021/jm9600196
• 作为产物：
  描述：

  3-azido-2-methylbut-3-en-2-ol 、 在 tris[2-phenylpyridinato-C²,N]iridium(III) 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以81%的产率得到2-(氰基甲基)-3-苯基丙酸甲酯
  参考文献：
  名称：

  通过叠氮化乙烯级联片段进行 自由基氰基甲基化† ‡

  摘要：

  在此，描述了用于自由基氰基甲基化的新方法。该过程是通过将自由基添加到叠氮化乙烯试剂3-叠氮基-2-甲基丁-3-烯-2-醇中而引发的，该自由基触发了级联碎片化机理，该机理由二氮和稳定的2-羟丙基自由基的损失驱动，最终实现了氰基甲基化。通过捕获在光氧化还原催化和非催化条件下由各种官能团产生的α-羰基，杂苄基，烷基，磺酰基和芳基，可以将氰甲基有效地引入一系列底物中。这种方法的价值可以通过药物的后期氰甲基化来例证。

  DOI：

  10.1039/c9sc01370a

文献信息

• US5776959A
  申请人：——

  公开号：US5776959A

  公开（公告）日：1998-07-07
• US6066666A
  申请人：——

  公开号：US6066666A

  公开（公告）日：2000-05-23
• 3,3-Dialkyl- and 3-Alkyl-3-Benzyl-Substituted 2-Pyrrolidinones:  A New Class of Anticonvulsant Agents
  作者：P. Amruta Reddy、Bonnie C. H. Hsiang、Tammy N. Latifi、Matthew W. Hill、Karen E. Woodward、Steven M. Rothman、James A. Ferrendelli、Douglas F. Covey

  DOI：10.1021/jm9600196

  日期：1996.1.1

  A series of 3,3-dialkyl- and 3-alkyl-3-benzyl-substituted 2-pyrrolidinones (lactams) have been prepared and evaluated for their anticonvulsant activities. In the pentylenetetrazole mouse seizure model, 3,3-diethyl lactam 7c and 3-benzyl-3-ethyl lactam 7j are the most effective anticonvulsants (ED(50) = 46 and 42 mg/kg, respectively) and have protective index (PI = TD50/ED(50)) values of 5.65 and 3.00, respectively. These protective index values compare favorably to those of the clinically used antiepileptic drugs ethosuximide (ED(50) = 161 mg/kg), phenobarbital (ED(50) = 22 mg/kg), and valproic acid (ED(50) = 133 mg/kg), which have PI values of 2.35, 4.00, and 2.12, respectively. The benzyl compounds [3-substituents are Bn, H (7h); Bn, Me (7i); and Bn, Et (7j)] are also very effective anticonvulsants against seizures induced by maximal electroshock (ED(50) = 41, 55, and 74 mg/kg, respectively) and have PI values of 3.51, 3.04, and 1.70, respectively. The corresponding PI values for phenobarbital and valproic acid are 1.37 and 5.18, respectively. As a class of anticonvulsants, the 3,3-disubstituted 2-pyrrolidinones have a broad spectrum of action and may be useful for the treatment of human epilepsies.
• Radical cyanomethylation <i>via</i> vinyl azide cascade-fragmentation
  作者：James R. Donald、Sophie L. Berrell

  DOI：10.1039/c9sc01370a

  日期：——

  Herein, a novel methodology for radical cyanomethylation is described. The process is initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggers a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilised 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl groups can be efficiently introduced into a range of

  在此，描述了用于自由基氰基甲基化的新方法。该过程是通过将自由基添加到叠氮化乙烯试剂3-叠氮基-2-甲基丁-3-烯-2-醇中而引发的，该自由基触发了级联碎片化机理，该机理由二氮和稳定的2-羟丙基自由基的损失驱动，最终实现了氰基甲基化。通过捕获在光氧化还原催化和非催化条件下由各种官能团产生的α-羰基，杂苄基，烷基，磺酰基和芳基，可以将氰甲基有效地引入一系列底物中。这种方法的价值可以通过药物的后期氰甲基化来例证。

表征谱图