(1S)-1-methyl-3-oxocyclohexane-1-carbonitrile

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-methyl-3-oxocyclohexane-1-carbonitrile
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: PSNUDZTXYBUGJI-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲基-2-环己烯-1-酮 、 N-[2-(甲氧基甲基)-1-吡咯烷基]甲亚胺 生成 (R)-1-methyl-3-oxocyclohexanecarbonitrile 、 (1S)-1-methyl-3-oxocyclohexane-1-carbonitrile
  参考文献：
  名称：

  Formaldehyde Dialkylhydrazones as Neutral Formyl Anion and Cyanide Equivalents:  Nucleophilic Addition to Conjugated Enones

  摘要：

  A versatile methodology for the nucleophilic formylation and cyanation of conjugated enones is reported. The procedure is based on the use of formaldehyde dimethylhydrazone, which, acting as a neutral formyl anion equivalent, adds to preformed trialkylsilyl-enone complexes. Both 4-(silyloxy)-3-enal hydrazones 3 or deprotected 4-oxo aldehyde monohydrazones 4 can be obtained as products depending on quenching conditions. In full analogy, an asymmetric version of the reaction using chiral formaldehyde SAMP-hydrazone as a neutral synthon of the chiral formyl anion has been developed, giving rise to the corresponding adducts 5 and 6 in good yields and with excellent diastereoselectivities (de 85-greater than or equal to 98%). Ozonolysis or HCl-mediated hydrolysis of adducts 4 and 6 readily affords racemic and optically enriched 4-oxo aldehydes 7, respectively. Additionally, high-yielding MMPP-oxidative cleavage of 4-oxo hydrazones 4 and 6 has been performed to obtain Li-oxo nitriles 8 in racemic and optically enriched forms, respectively. In this way, interesting chiral bifunctional building blocks, some of them bearing newly created stereogenic quaternary centers, have been efficiently synthesized.

  DOI：

  10.1021/jo970481d

文献信息

• Cycloalkylamines as monoamine reuptake inhibitors
  申请人：Sunovion Pharmaceuticals Inc.

  公开号：US10562878B2

  公开（公告）日：2020-02-18

  The invention relates to novel cyclohexylamine derivatives and their use in the treatment and/or prevention of central nervous system (CNS) disorders, such as depression, anxiety, schizophrenia and sleep disorder as well as methods for their synthesis. The invention also relates to pharmaceutical compositions containing the compounds of the invention, as well as methods of inhibiting reuptake of endogenous monoamines, such as dopamine, serotonin and norepinephrine from the synaptic cleft and methods of modulating one or more monoamine transporter.

  本发明涉及新型环己胺衍生物及其在治疗和/或预防中枢神经系统（CNS）疾病（如抑郁症、焦虑症、精神分裂症和睡眠障碍）中的用途及其合成方法。本发明还涉及含有本发明化合物的药物组合物，以及抑制内源性单胺（如多巴胺、5-羟色胺和去甲肾上腺素）从突触间隙再摄取的方法和调节一种或多种单胺转运体的方法。