methyl 5-cyano-5-(4-methoxyphenyl)-2-oxocyclohexanecarboxylate | 56326-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 5-cyano-5-(4-methoxyphenyl)-2-oxocyclohexanecarboxylate
• 英文别名: 2-carbomethoxy-4-cyano-4-(p-anisyl)cyclohexanone；2-Carbomethoxy-4-cyano-4-(p-methoxyphenyl)cyclohexanone；methyl 5-cyano-5-(4-methoxyphenyl)-2-oxocyclohexane-1-carboxylate
• CAS: 56326-96-6
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: MMBYSSNHJFUDAN-UHFFFAOYSA-N

物化性质

• 熔点：
  63.5-66 °C
• 沸点：
  461.2±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-cyano-5-(4-methoxyphenyl)-2-oxocyclohexanecarboxylate 在 硫酸 、 溶剂黄146 作用下， 生成 1-(4-甲氧苯基)-4-氧代环己甲腈
  参考文献：
  名称：

  丁苯酮作为降压药。4-芳基-4-（羟甲基）环己胺的衍生物。

  摘要：

  描述了从相应的4-氰基-4-苯基环己酮-1-酮开始制备4-芳基-4-（羟甲基）环己-1-基胺的丁苯酮衍生物。两个环都有不同的取代基；对4-苯基-4-（羟甲基）环己-1-基胺的两种异构体进行了表征。与缺乏羟甲基的化合物相比，在丁苯酮上进行对氟取代的那些衍生物在大鼠中表现出降压活性，而CNS活性降低。讨论了取代对4-芳基环的影响。

  DOI：

  10.1021/jm00240a014
• 作为产物：
  描述：

  4-Cyano-4-(p-anisyl)-pimelinsaeuredimethylester 在 potassium tert-butylate 作用下， 生成 methyl 5-cyano-5-(4-methoxyphenyl)-2-oxocyclohexanecarboxylate
  参考文献：
  名称：

  丁苯酮作为降压药。4-芳基-4-（羟甲基）环己胺的衍生物。

  摘要：

  描述了从相应的4-氰基-4-苯基环己酮-1-酮开始制备4-芳基-4-（羟甲基）环己-1-基胺的丁苯酮衍生物。两个环都有不同的取代基；对4-苯基-4-（羟甲基）环己-1-基胺的两种异构体进行了表征。与缺乏羟甲基的化合物相比，在丁苯酮上进行对氟取代的那些衍生物在大鼠中表现出降压活性，而CNS活性降低。讨论了取代对4-芳基环的影响。

  DOI：

  10.1021/jm00240a014

文献信息

• 4-Arylcyclohexylamines
  申请人：The Upjohn Company

  公开号：US03979444A1

  公开（公告）日：1976-09-07

  The invention relates to novel 4-hydroxymethyl(acyloxymethyl and methyl)-4-arylcyclohexylamines embraced by the formula ##SPC1## Wherein Ar is an aromatic ring selected from the group consisting of phenyl and naphthyl, each of which has from zero through three substituents independently selected from the group consisting of fluorine, chlorine, bromine, lower alkyl of one through three carbon atoms, lower alkoxy of one through three carbon atoms, and lower alkylthio of one through three carbon atoms; Z is selected from the group consisting of hydrogen, hydroxy and lower acyloxy of one through four carbon atoms; .about. is a generic expression denoting cis and trans stereoconfiguration and mixtures thereof, with the proviso that when the stereoconfiguration of the linkage connecting the cyclohexane ring and CH.sub.2 Z is cis to the amino group, the linkage connecting the cyclohexane and Ar rings is trans, and vice versa; R.sup.1 is selected from the group consisting of hydrogen and lower alkyl of one through three carbon atoms; R.sup.2 is selected from the group consisting of hydrogen, lower alkyl of one through three carbon atoms, ##EQU1## WHEREIN N IS 2 THROUGH 5 AND Ar has the same meaning as above; R.sup.1 and R.sup.2 taken together with --N< is a saturated heterocyclic amino radical selected from the group consisting of unsubstituted and substituted pyrrolidino, piperidino, hexamethylenimino, morpholino and piperazino; and pharmacologically acceptable acid addition salts thereof. It also relates to intermediates and processes for the preparation of the aforesaid novel compounds (I) and novel derivatives thereof. The administration to humans and animals of the novel compounds (I) depresses their central nervous systems and lowers their blood pressures.

  该发明涉及一种新型4-羟甲基(酰氧甲基和甲基)-4-芳基环己胺，其化学式如下：其中Ar是从苯基和萘基中选择的芳香环，每个环上独立选择的取代基包括氟、氯、溴、1至3个碳原子的低烷基、1至3个碳原子的低烷氧基和1至3个碳原子的低烷基硫基；Z选择自氢、羟基和1至4个碳原子的低酰氧基；~表示顺式和反式立体构型及其混合物，但当连接环己烷环和CH2Z的立体构型为顺时，连接环己烷环和Ar环的连接是反式，反之亦然；R1选择自氢和1至3个碳原子的低烷基；R2选择自氢、1至3个碳原子的低烷基、其中N为2至5且Ar的含义与上述相同；R1和R2与-N<一起构成从未取代和取代的吡咯啉基、哌啶基、六亚甲基基、吗啉基和哌嗪基中选择的饱和杂环氨基基团；以及其药理学上可接受的酸盐。它还涉及中间体和用于制备上述新化合物(I)及其新衍生物的过程。将该新型化合物(I)用于人类和动物，可抑制其中枢神经系统并降低其血压。
• 4-Pyrrolidino-cyclohexanone ketals
  申请人：The Upjohn Company

  公开号：US04180584A1

  公开（公告）日：1979-12-25

  A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for snythesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.

  一类新的4-氨基-4-芳基环己酮、它们的缩酮和酸加成盐已被合成并发现对缓解动物疼痛有用。它们的镇痛活性似乎是高级别的，另外一些表现出麻醉拮抗活性，有助于改变其他镇痛剂引起的心血管、呼吸和行为抑制。几种显示出混合的镇痛和麻醉拮抗活性。该类化合物的首选物是4-（间羟基苯基）-4-二甲氨基环己酮乙二醇缩酮和4-（间羟基苯基）-4-（正丁基甲基氨基）环己酮乙二醇缩酮，作为自由碱和它们的盐酸盐。描述了合成和中间体的过程。揭示了单元剂量形式和治疗方法。
• 4-Amino-4-phenylcyclohexanone ketal compositions and process of use
  申请人：The Upjohn Company

  公开号：US04065573A1

  公开（公告）日：1977-12-27

  A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for synthesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.

  一类新的4-氨基-4-芳基环己酮、它们的缩醛和酸加成盐已经被合成，并被发现在动物止痛方面有用。它们的镇痛活性似乎是高级别的，另外一些表现出镇痛拮抗剂活性，这对于改变其他镇痛药物引起的心血管、呼吸和行为抑制是有用的。其中一些表现出混合的镇痛和镇痛拮抗剂活性。该类化合物的首选物是4-(间羟基苯基)-4-二甲氨基环己酮乙烯缩醛，以及4-(间羟基苯基)-4-(正丁基甲基氨基)环己酮乙烯缩醛，作为自由碱和它们的盐酸盐。描述了合成和中间体的过程。揭示了单元剂量形式和治疗方法。
• US3979444A
  申请人：——

  公开号：US3979444A

  公开（公告）日：1976-09-07
• US4065573A
  申请人：——

  公开号：US4065573A

  公开（公告）日：1977-12-27