Acetic acid 1-(4-methoxy-phenyl)-4-oxo-cyclohexylmethyl ester | 56327-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Acetic acid 1-(4-methoxy-phenyl)-4-oxo-cyclohexylmethyl ester
• 英文别名: Cyclohexanone, 4-[(acetyloxy)methyl]-4-(4-methoxyphenyl)-；[1-(4-methoxyphenyl)-4-oxocyclohexyl]methyl acetate
• CAS: 56327-08-3
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: VCPSXGYQRSCGMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetic acid 1-(4-methoxy-phenyl)-4-oxo-cyclohexylmethyl ester 在 吡啶 、 sodium tetrahydroborate 、 potassium carbonate 、 potassium iodide 作用下， 生成 1-(4-Fluoro-phenyl)-4-[4-hydroxymethyl-4-(4-methoxy-phenyl)-cyclohexylamino]-butan-1-one
  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：

  8-(4-methoxy-phenyl)-1,4-dioxa-spiro[4.5]decane-8-carboxylic acid 、 乙酸酐 生成 Acetic acid 1-(4-methoxy-phenyl)-4-oxo-cyclohexylmethyl ester
  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.

  本发明涉及一种新型的4-羟甲基（酰氧甲基和甲基）-4-芳基环己胺，其公式为##SPC1##其中Ar是从苯基和萘基选择的芳香环，每个环都有从0到3个取自氟、氯、溴、1至3个碳原子的低级烷基、1至3个碳原子的低级烷氧基和1至3个碳原子的低级烷基硫基的官能团自由置换；Z选择自氢、羟基和1至4个碳原子的低级酰氧基的官能团自由置换；∼是表示顺式和反式立体构型及其混合物的通用表达式，但当连接环己烷环和CH.sub.2 Z的立体构型为顺式时，连接环己烷环和Ar环的立体构型为反式，反之亦然；R.sup.1选择自氢和1至3个碳原子的低级烷基的官能团自由置换；R.sup.2选择自氢、1至3个碳原子的低级烷基、## EQU1##其中N为2至5，Ar具有与上述相同的含义；R.sup.1和R.sup.2与--N <一起取代为选自未取代和取代的吡咯烷基、哌啶烷基、六亚甲基亚胺基、吗啉基和哌嗪基的饱和杂环氨基基团；以及其药学上可接受的酸加盐。本发明还涉及上述新型化合物（I）及其新型衍生物的中间体和制备方法。将新型化合物（I）用于人类和动物可以抑制其中枢神经系统并降低其血压。
• LEDNICER D.; EMMERT D. E.; RUDZIK A. D.; GRAHAM B. E., J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 6, 593-599
  作者：LEDNICER D.、 EMMERT D. E.、 RUDZIK A. D.、 GRAHAM B. E.

  DOI：——

  日期：——
• US3979444A
  申请人：——

  公开号：US3979444A

  公开（公告）日：1976-09-07
• Butyrophenones as hypotensive agents. Derivatives of 4-aryl-4-(hydroxymethyl)cyclohexylamine
  作者：Daniel Lednicer、D. Edward Emmert、Alan D. Rudzik、Boyd E. Graham

  DOI：10.1021/jm00240a014

  日期：1975.6

  preparation of butyrophenone derivatives of 4-aryl-4-(hydroxymethyl)cyclohex-1-ylamines starting from the corresponding 4-cyano-4-phenylcyclohexan-1-ones is described. Substitution was varied with both rings; both isomers of 4-phenyl-4-(hydroxymethyl)cyclohex-1-ylamine were characterized. Those derivatives which carried p-fluoro substitution on the butyrophenone exhibited hypotensive activity in the rat with

  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。