4-氰-4-(3,4-二氯苯)环己酮 | 65619-30-9

• 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: 4-氰-4-(3,4-二氯苯)环己酮
• 中文别名: 1-(3,4-二氯苯基)-4-氧代环己烷甲腈；4-(3,4-二氯苯基l)-4-氰基环己酮
• 英文名称: 4-Cyano-4-(3',4'-dichlorophenyl)cyclohexanone
• 英文别名: 1-(3,4-Dichlorophenyl)-4-oxocyclohexanecarbonitrile；1-(3,4-dichlorophenyl)-4-oxocyclohexane-1-carbonitrile
• CAS: 65619-30-9
• 化学式: C₁₃H₁₁Cl₂NO
• 分子量: 268.142
• InChiKey: YDVFTCZQEZJUIH-UHFFFAOYSA-N

物化性质

• 熔点：
  154-156°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 安全说明：
  S22,S36/37
• 危险类别码：
  R22
• 海关编码：
  2926909090
• 危险品运输编号：
  UN 3276

反应信息

• 作为反应物：
  描述：

  4-氰-4-(3,4-二氯苯)环己酮 在 pseudomonas fluorescens lipase 、 氧气 、 臭氧 、 lithium hexamethyldisilazane 、 正丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.75h， 生成 (S)-(-)-methyl 4-cyano-4-(3',4'-dichlorophenyl)-6-oxo-hexanoate
  参考文献：
  名称：

  Chemoenzymatic synthesis of a tachykinin NK-2 antagonist

  摘要：

  A non-peptide tachykinin antagonist has been synthesized in a short and efficient four step sequence starting from a chiral enol acetate, which was obtained in enantiomerically pure form by resolution using a lipase catalysed transesterification reaction. The biotransformation was optimized in terms of solvent, temperature and immobilization method used. Oxidative cleavage of the (+)-enol acetate to give the key aldehyde ester intermediate could be achieved indirectly by oxidative rearrangement to an enone followed by Baeyer-Villiger oxidation and ring opening, or by epoxidation, rearrangement and oxidative cleavage or most directly by ozonolysis. X-Ray crystallographic analysis of a camphanic ester derivative of an ester alcohol confirmed that the absolute configuration of the enol acetate was (S). (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)00796-7
• 作为产物：
  描述：

  3,4-二氯苯乙腈 在 硫酸 、 potassium tert-butylate 、 四甲基氢氧化铵 、 溶剂黄146 作用下， 生成 4-氰-4-(3,4-二氯苯)环己酮
  参考文献：
  名称：

  DE2723937

  摘要：

  公开号：

文献信息

• Desymmetrisation of 4,4-disubstituted cyclohexanones by enzyme-catalysed resolution of their enol acetates
  作者：Graham Allan、Andrew J. Carnell、Maria Luisa Escudero Hernandez、Alan Pettman

  DOI：10.1039/b005466f

  日期：——

  Enol acetates 3–10 derived from prochiral 4,4-disubstituted cyclohexanones can be resolved with Pseudomonas fluorescens lipase to give enantiomerically pure (>99% ee) enol esters by transesterification with n-BuOH. The product ketones are prochiral and can easily be recycled giving an overall desymmetrisation of the ketone. Highest selectivity was obtained for substrates containing a 4-cyano and 4-aryl or a 4-benzyloxy substituent. The methodology was compared to asymmetric deprotonation–enolate trapping using the chiral base (S,S)-bis(α-methylbenzyl)amide which gave low (54–64%) ee’s for this class of ketones.

  来自对称的4,4-二取代环己酮的醇乙酸酯3-10可以通过荧光假单胞菌脂肪酶进行分离，以转酯化反应与正丁醇生成对映体纯度>99% ee的醇酯。生成的酮是对称的，可以很容易地循环利用，从而实现酮的整体去对称化。对于含有4-氰基和4-芳基或4-苄氧基取代基的底物，获得了最高的选择性。该方法与使用手性碱(S,S)-双(α-甲基苯甲酰)胺的非对称去质子化-烯醇捕获进行了比较，该方法在这一类酮中获得了较低的对映体纯度(54-64% ee)。
• One-pot deracemisation of an enol acetate derived from a prochiral cyclohexanone
  作者：Graham R Allan、Andrew J Carnell、Wolfgang Kroutil

  DOI：10.1016/s0040-4039(01)01156-x

  日期：2001.8

  method for the deracemisation of the enol acetate 1 derived from the prochiral 4,4-disubstituted cyclohexanone 2 has been developed using the combination of Pseudomonas fluorescens lipase and potassium t-butoxide/isopropenyl acetate to give the enantiomerically pure enol acetate (S)-1 in 82% yield. Calculations based on the inherent enantioselectivity of the lipase (E) allowed an estimation of the optimum

  使用荧光假单胞菌脂肪酶和叔丁醇钾/乙酸异丙烯酯的组合，开发了一种用于从手性4,4-二取代的环己酮2衍生的烯醇式乙酸酯1脱除油的单罐方法，从而得到对映体纯的烯醇式乙酸酯（S）-1，产率为82％。基于脂肪酶（E）的固有对映选择性的计算允许在回收酮之前估算每个酶步骤的最佳理论转化率。
• [EN] 1,2,4-TRIOXOLANE ANTIMALARIALS<br/>[FR] ANTIPALUDIQUES A BASE DE 1,2,4-TRIOXOLANE
  申请人：MEDICINES MALARIA VENTURE MMV

  公开号：WO2003000676A1

  公开（公告）日：2003-01-03

  A means and method for treating malaria, schistosomiasis, and cancer using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably substituted at the 4-position. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.

  本发明涉及使用螺环或双螺环1,2,4-三噁烷治疗疟疾、血吸虫病和癌症的方法和手段。首选的1,2,4-三噁烷包括一个螺环戊烷基团位于三噁烷基团的一侧，以及一个螺环己基位于三噁烷基团的另一侧，其中螺环己环在4位处优选被取代。与青蒿素半合成衍生物相比，本发明的化合物结构简单，易于合成，无毒，并且对疟原虫具有很强的杀灭作用。
• Cycloalkylamines as monoamine reuptake inhibitors
  申请人：Shao Liming

  公开号：US20070203111A1

  公开（公告）日：2007-08-30

  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中枢神经系统（CNS）疾病的治疗和/或预防中的应用，例如抑郁症、焦虑症、精神分裂症和睡眠障碍，以及它们的合成方法。本发明还涉及包含本发明化合物的制药组合物，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中再摄取的方法和调节一个或多个单胺转运体的方法。
• CYCLOALKYLAMINES AS MONOAMINE REUPTAKE INHIBITORS
  申请人：Shao Liming

  公开号：US20100190861A1

  公开（公告）日：2010-07-29

  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基胺衍生物及其在治疗和/或预防中枢神经系统（CNS）疾病方面的应用，例如抑郁症，焦虑症，精神分裂症和睡眠障碍，以及它们的合成方法。本发明还涉及含有本发明化合物的制药组合物，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中再摄取的方法，以及调节一个或多个单胺转运体的方法。