N-methyl-8-(thiophen-2-yl)-1,4-dioxaspiro[4.5]decan-8-amine | 79741-38-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-methyl-8-(thiophen-2-yl)-1,4-dioxaspiro[4.5]decan-8-amine
• 英文别名: N-methyl-8-thiophen-2-yl-1,4-dioxaspiro[4.5]decan-8-amine
• CAS: 79741-38-1
• 化学式: C₁₃H₁₉NO₂S
• 分子量: 253.365
• InChiKey: QTFVTGPPCPETJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-8-(thiophen-2-yl)-1,4-dioxaspiro[4.5]decan-8-amine 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 54.0h， 生成 4-(dimethylamino)-4-(thiophen-2-yl)cyclohexanone
  参考文献：
  名称：

  4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring

  摘要：

  Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues. Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated. Synthesis starts by double Michael reaction of acrylate on arylacetonitriles. Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3. Isocyanates were then converted to the title compounds. Analgesic activity is very sensitive to the nature and position of the substitutent on the aromatic ring. The most potent compounds in this series (p-CH3, p-Br) showed 50% the potency of morphine. Deletion of the ring oxygen abolishes activity.

  DOI：

  10.1021/jm00178a014
• 作为产物：
  描述：

  4-(2-thienyl)-4-ethoxycarbonylaminocyclohexanone ethylene ketal 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-methyl-8-(thiophen-2-yl)-1,4-dioxaspiro[4.5]decan-8-amine
  参考文献：
  名称：

  4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring

  摘要：

  Investigation of central nervous system activity of phenylcyclohexylamines was continued by preparation of "reversed" analogues. Following the unexpected finding of analgesic activity with 1-(dimethylamino)-1-phenylcyclohexylamine, the SAR of the series was investigated. Synthesis starts by double Michael reaction of acrylate on arylacetonitriles. Following cyclization, decarboxylation, ketalization, and saponification, the geminally substituted acid is rearranged to the isocyanate by means of (C6H5O)2PON3. Isocyanates were then converted to the title compounds. Analgesic activity is very sensitive to the nature and position of the substitutent on the aromatic ring. The most potent compounds in this series (p-CH3, p-Br) showed 50% the potency of morphine. Deletion of the ring oxygen abolishes activity.

  DOI：

  10.1021/jm00178a014

文献信息

• Spirocyclic Azaindole Derivatives
  申请人：Zemolka Saskia

  公开号：US20090156593A1

  公开（公告）日：2009-06-18

  The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.

  该发明涉及取代的氮杂吲哚衍生物，其制备方法，含有该化合物的药物以及使用取代的氮杂吲哚衍生物来生产药物。
• Spirocyclic azaindole derivatives
  申请人：Zemolka Saskia

  公开号：US08399503B2

  公开（公告）日：2013-03-19

  The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.

  本发明涉及取代的氮杂吲哚衍生物，其制备方法，含有该化合物的药物以及使用取代的氮杂吲哚衍生物制备药物的用途。
• SPIROCYCLISCHE AZAINDOL-DERIVATE
  申请人：Grünenthal GmbH

  公开号：EP2041142B1

  公开（公告）日：2013-10-09
• US8399503B2
  申请人：——

  公开号：US8399503B2

  公开（公告）日：2013-03-19
• [DE] SPIROCYCLISCHE AZAINDOL-DERIVATE<br/>[EN] SPIROCYCLIC AZAINDOLE DERIVATIVES<br/>[FR] DÉRIVÉS AZAINDOLIQUES SPIROCYCLIQUES
  申请人：GRUENENTHAL GMBH

  公开号：WO2008009416A1

  公开（公告）日：2008-01-24

  [EN] The invention relates to substituted azaindole derivatives, to methods for the production thereof, to medicaments containing said compounds and to the use of substituted azaindole derivatives for producing medicaments.
  [FR] La présente invention concerne des dérivés azaindoliques substitués, un procédé de production desdits dérivés, des médicaments contenant ces composés et l'utilisation de dérivés azaindoliques substitués dans le production de médicaments.
  [DE] Die vorliegende Erfindung betrifft substituierte Azaindolderivate, Verfahren zu deren Herstellung, Arzneimittel enthaltend diese Verbindungen und die Verwendung von substituierten Azaindolderivaten zur Herstellung von Arzneimitteln.