4,4-dimethyl-pent-2-enenitrile | 39168-14-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4-dimethyl-pent-2-enenitrile
• 英文别名: 4,4-Dimethyl-pent-2-ennitril；4,4-Dimethylpent-2-enenitrile
• CAS: 39168-14-4
• 化学式: C₇H₁₁N
• 分子量: 109.171
• InChiKey: GCTNTYCHYKCHEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-pent-2-enenitrile 以 甲醇 、 乙醚 为溶剂， 生成 Z-4,4-Dimethyl-3-methoxy-2-pentennitril
  参考文献：
  名称：

  空间和极性效应在确定力顺-反-烯烃对的平衡位置中的影响

  摘要：

  一系列α,β-不饱和腈和酯在β-位被叔丁基或异丙基取代，在另一个β-位被甲氧基、硫代乙氧基二甲氨基、氯和氢取代。从催化或热上实现的顺反平衡对异构体稳定性的评估支持早期的观察结果，即空间和极性因素保持β-甲氧基转为腈或甲氧基的强烈趋势，即使与叔丁基相反团体。通过用异丙基或叔丁基代替 β-甲基，可以克服在 β-氯巴豆酸甲酯中氯基团优先与碳甲氧基基团反式的趋势。

  DOI：

  10.1139/v70-349
• 作为产物：
  描述：

  特戊醛 在 sodium hydroxide 、 铜 作用下， 生成 4,4-dimethyl-pent-2-enenitrile
  参考文献：
  名称：

  Equilibria of the Boric Acid--Mannitol Complexes

  摘要：

  DOI：

  10.1021/ja01178a528

文献信息

• New methods and reagents in organic synthesis. 41. Lithium trimethylsilyldiazomethane. A new synthon for the preparation of pyrazoles from α,β-unsaturated nitriles
  作者：Tayahiko Aoyama、Sumie Inoue、Tokoyuki Shioiri

  DOI：10.1016/s0040-4039(00)99904-0

  日期：1984.1

  Lithium trimethylsilyldiazomethane reacts smoothly with various α,β-unsaturated nitriles to give 3(or 5)-trimethylsilylpyrazoles in good yields.

  三甲基硅烷基重氮甲烷锂可与各种α，β-不饱和腈平稳反应，以高收率得到3（或5）-三甲基硅烷基吡唑。
• Novel pyrrolidine melanin-concentrating hormone receptor 1 antagonists with reduced hERG inhibition
  作者：Brian M. Fox、Reina Natero、Kevin Richard、Richard Connors、Philip M. Roveto、Holger Beckmann、Katrin Haller、Justin Golde、Shou-Hua Xiao、Frank Kayser

  DOI：10.1016/j.bmcl.2011.02.046

  日期：2011.4

  We discovered novel pyrrolidine MCHR1 antagonist 1 possessing moderate potency. Profiling of pyrrolidine 1 demonstrated that it was an inhibitor of the hERG channel. Investigation of the structure–activity relationship of this class of pyrrolidines allowed us to optimize the MCHR1 potency and decrease the hERG inhibition. Increasing the acidity of the amide proton by converting the benzamide in lead

  我们发现新型吡咯烷MCHR1拮抗剂1具有中等效力。吡咯烷1的分析表明它是hERG通道的抑制剂。此类吡咯烷类的结构与活性之间的关系研究使我们能够优化MCHR1效能并降低hERG抑制作用。通过将铅1中的苯甲酰胺转化为苯胺来增加酰胺质子的酸度，可提供一位数的纳摩尔级MCHR1拮抗剂，同时用具有增强极性的烷基取代1的二甲氧基苯基环可大大降低hERG抑制作用。
• P(RNCH₂CH₂)₃N-Catalyzed Synthesis of β-Hydroxy Nitriles
  作者：Philip Kisanga、Dale McLeod、Bosco D'S、John Verkade

  DOI：10.1021/jo981858y

  日期：1999.4.1

  We herein report the successful synthesis of beta-hydroxy nitriles in very good to excellent yields from aldehydes and ketones in a simple reaction that is promoted by strong nonionic bases of the. title type. The reaction occurs in the presence of magnesium salts which activate the carbonyl group and stabilizes the enolate thus produced.
• Direct Synthesis of α,β-Unsaturated Nitriles Catalyzed by Nonionic Superbases
  作者：Bosco A. D'Sa、Philip Kisanga、John G. Verkade

  DOI：10.1021/jo972343u

  日期：1998.6.1

  We report herein the use of 3-30 mol % of a new class of tricyclic strong nonionic Lewis bases P(MeNCH2CH2)(3)N and P(HNCH2CH2)(i-PrNCH2CH2)(2)N for the direct catalytic synthesis of a variety of functionalized alpha,beta-unsaturated nitriles in high yields from aldehydes and acetonitrile or benzyl cyanide at 40-50 degrees C. Evidence for a novel mechanistic pathway proposed for this reaction in a polar protic solvent such as methanol, and a nonpolar aprotic solvent such as benzene is also presented. Under these conditions, primary and secondary aliphatic aldehydes do not condense satisfactorily with acetonitrile to give the alpha,beta-unsaturated nitrile, and ketones do not condense with either benzyl cyanide or acetonitrile.
• Equilibria of the Boric Acid--Mannitol Complexes
  作者：Sidney D. Ross、Arthur J. Catotti

  DOI：10.1021/ja01178a528

  日期：1949.10