(E)-3-methyl-5,5-dimethyl-2-cyclohexenylidene acetonitrile | 69697-21-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (E)-3-methyl-5,5-dimethyl-2-cyclohexenylidene acetonitrile
• 英文别名: Acetonitrile, (3,5,5-trimethyl-2-cyclohexen-1-ylidene)-, (Z)-；(2E)-2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)acetonitrile
• CAS: 69697-21-8
• 化学式: C₁₁H₁₅N
• 分子量: 161.247
• InChiKey: LRSGHOGSSBSTOT-WMZJFQQLSA-N

物化性质

• 沸点：
  256.2±9.0 °C(Predicted)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (E)-3-methyl-5,5-dimethyl-2-cyclohexenylidene acetonitrile 在 二异丁基氢化铝 、 silica gel 作用下， 以 甲苯 、 水 为溶剂， 反应 2.5h， 生成 (2E)-(3,5,5-TRIMETHYLCYCLOHEX-2-EN-1-YLIDENE)ACETALDEHYDE
  参考文献：
  名称：

  Reverse synthetic methods for making organic non-linear optical materials

  摘要：

  一种制备有机非线性光学色团的反向合成策略涉及从电子受吸引端向电子供给端逐步构建色团。

  公开号：

  US20050288445A1
• 作为产物：
  描述：

  异佛尔酮 、 氰甲基磷酸二乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 2.25h， 生成 (E)-3-methyl-5,5-dimethyl-2-cyclohexenylidene acetonitrile
  参考文献：
  名称：

  Reverse synthetic methods for making organic non-linear optical materials

  摘要：

  一种制备有机非线性光学色团的反向合成策略涉及从电子受吸引端向电子供给端逐步构建色团。

  公开号：

  US20050288445A1

文献信息

• [EN] ANTICONVULSANT COMPOUNDS<br/>[FR] COMPOSÉS ANTICONVULSIVANTS
  申请人：OWEN-BARRY PHARMACEUTICALS INC

  公开号：WO2016191855A1

  公开（公告）日：2016-12-08

  The present invention relates to diene nitrile compounds with anti-convulsant activity and can also be used to treat pain. These compounds are useful in modulating voltage-gated sodium channel activity and can be used in the treatment of epilepsy and chronic or acute pain. E and Z mixtures of compounds of formula (I) are used to eliminate or reduce convulsant activity or epileptic seizures in patients. The compounds prolong the time required for voltage-gated sodium channels to recover from a normally inactive state induced by depolarization and tend to suppress abnormal brain behavior. The present application relates to compounds and methods for reducing the severity of convulsant activity, or epileptic seizures.

  本发明涉及具有抗抽搐活性的二烯腈化合物，也可用于治疗疼痛。这些化合物在调节电压门控钠通道活性方面很有用，并可用于治疗癫痫和慢性或急性疼痛。化合物的E和Z混合物（式(I)）用于消除或减少患者的抽搐活性或癫痫发作。这些化合物延长了电压门控钠通道从脱极化引起的正常不活动状态恢复所需的时间，并倾向于抑制异常的大脑行为。本申请涉及减轻抽搐活性或癫痫发作严重程度的化合物和方法。
• Reaction de wittig-horner entre phosphonates et cyclohexenones β-substituees.
  作者：Serge Geribaldi、Michel Rouillard

  DOI：10.1016/s0040-4020(01)80938-8

  日期：1991.1

  attempted in order to prepare α,β,γ,δ-unsaturated nitriles via the Wittig-Horner reaction of β-substituted cyclohex-2-en-1-ones with diethyl cyanomethyl phosphonate. Among them, the one using NaH as base in refluxing THF gives only the products resulting from carbonyl attack, in good yields. The stereochemistry of the reaction is discussed.

  为了通过β-取代的环己-2-烯-1-酮与氰基甲基膦酸二乙酯的Wittig-Horner反应制备α，β，γ，δ-不饱和腈，尝试了各种方法。其中，在回流的THF中使用NaH作为碱的化合物仅以高收率得到了羰基侵蚀产生的产物。讨论了反应的立体化学。
• 1H NMR utilization of through-space effects in configurational assignments. I—application to nitriles; determination of the separate effects of the electric field and anisotropy of the CN group
  作者：Michel Rouillard、Serge Geribaldi、Jean Khazarian、Marcel Azzaro

  DOI：10.1002/mrc.1270130504

  日期：1980.5

  AbstractThe changes in chemical shift induced by isomerization for all the ring protons of the Z‐ and E‐5,5‐dimethyl‐2‐cyclohexenylidene acetonitriles depend only on the through‐space effects of the cyano group. The configurational assignments were made taking into consideration the anisotropic and electric field effects, either separately or together. In the first case, the total effects are ΔXCNT=−14.7×10−6cm3 mol−1 and bμCNT=14.7×10−30 cm3, respectively. The second approach allows the estimation of the values ΔXCN=−4.9 × 10−6 cm3 mol−1 and bμCN=9.8 × 10−3 cm3, reflecting the combined contributions of magnetic anisotropy and electric field to the total effect.
• ANTICONVULSANT COMPOUNDS
  申请人：OWEN-BARRY PHARMACEUTICALS INC.

  公开号：US20160355469A1

  公开（公告）日：2016-12-08

  The present application relates to compounds and methods for reducing the severity of convulsant activity, or epileptic seizures.
• Reverse synthetic methods for making organic non-linear optical materials
  申请人：Li Sheng

  公开号：US20050288445A1

  公开（公告）日：2005-12-29

  A reverse synthetic strategy for making organic non-linear optical chromophores involves building up the chromophore from the electron-withdrawing end toward the electron-donating end.

  一种制备有机非线性光学色团的反向合成策略涉及从电子受吸引端向电子供给端逐步构建色团。