4-tert-Butyl-cyclohexan-diessigsaeure-(1,1) | 93807-49-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-tert-Butyl-cyclohexan-diessigsaeure-(1,1)
• 英文别名: 4-tert-Butyl-1,1-cyclohexanediacetic acid；3,3-[(3-tert-butyl)pentamethylene]glutaric acid；4-t-butylcyclohexyl-1,1-diacetic acid；2-[4-Tert-butyl-1-(carboxymethyl)cyclohexyl]acetic acid
• CAS: 93807-49-9
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: HDSYFUVAVYGQEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-tert-Butyl-cyclohexan-diessigsaeure-(1,1) 在 乙酸酐 作用下， 反应 4.0h， 生成 4-tert.-Butyl-cyclohexan-diessigsaeure-(1,1)-anhydrid
  参考文献：
  名称：

  Antiarthritic and supressor cell inducing activity of azaspiranes: structure-function relationships of a novel class of immunomodulatory agents

  摘要：

  Spirogermanium (1; 8,8-diethyl-N,N-dimethyl-2-aza-8- germaspiro[4.5]decane-2-propanamine dihydrochloride) is a potent cytotoxic agent in vitro which has demonstrated limited activity in experimental animal tumor models. Subsequently, it has been reported that spirogermanium has antiarthritic and suppressor cell-inducing activity. We have synthesized a series of substituted 8-hetero-2-azaspiro[4.5]decane and 9-hetero-3-azaspiro[5.5]undecane analogues of spirogermanium to identify the heteroatom requirements for in vivo antiarthritic and suppressor cell-inducing activity. This structure-activity relationship study has identified that appropriately substituted silicon and carbon analogues of spirogermanium retain both antiarthritic and immunosuppressive activity, with the 8,8-dipropyl (carbon) analogue being among the most active. Following the identification of N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride (9) as a more active analogue than spirogermanium, a series of 8,8-dipropyl analogues with various amine substituents were synthesized. A number of these analogues had activity similar to that of 9. A correlation between activity in the adjuvant arthritic rat and the ability to induce suppressor cells (r = 0.894, p less than 0.001) suggests an association between the two pharmacologic effects. While the precise biochemical mechanism(s) for the pharmacological activity is unclear, these data suggest that compounds within this series, e.g., N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride, may provide effective therapy in diseases of autoimmune origin and/or the prevention of rejection in tissue transplantation.

  DOI：

  10.1021/jm00173a010
• 作为产物：
  描述：

  2,4-Dioxo-9-t-butyl-1,5-dicyan-3-azaspiro<5.5>undecan 在 盐酸 、 水 、 溶剂黄146 作用下， 反应 84.0h， 生成 4-tert-Butyl-cyclohexan-diessigsaeure-(1,1)
  参考文献：
  名称：

  Antiarthritic and supressor cell inducing activity of azaspiranes: structure-function relationships of a novel class of immunomodulatory agents

  摘要：

  Spirogermanium (1; 8,8-diethyl-N,N-dimethyl-2-aza-8- germaspiro[4.5]decane-2-propanamine dihydrochloride) is a potent cytotoxic agent in vitro which has demonstrated limited activity in experimental animal tumor models. Subsequently, it has been reported that spirogermanium has antiarthritic and suppressor cell-inducing activity. We have synthesized a series of substituted 8-hetero-2-azaspiro[4.5]decane and 9-hetero-3-azaspiro[5.5]undecane analogues of spirogermanium to identify the heteroatom requirements for in vivo antiarthritic and suppressor cell-inducing activity. This structure-activity relationship study has identified that appropriately substituted silicon and carbon analogues of spirogermanium retain both antiarthritic and immunosuppressive activity, with the 8,8-dipropyl (carbon) analogue being among the most active. Following the identification of N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride (9) as a more active analogue than spirogermanium, a series of 8,8-dipropyl analogues with various amine substituents were synthesized. A number of these analogues had activity similar to that of 9. A correlation between activity in the adjuvant arthritic rat and the ability to induce suppressor cells (r = 0.894, p less than 0.001) suggests an association between the two pharmacologic effects. While the precise biochemical mechanism(s) for the pharmacological activity is unclear, these data suggest that compounds within this series, e.g., N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride, may provide effective therapy in diseases of autoimmune origin and/or the prevention of rejection in tissue transplantation.

  DOI：

  10.1021/jm00173a010

文献信息

• [EN] 4-T-BUTYLGABAPENTIN AND ITS SYNTHESIS<br/>[FR] 4-T-BUTYLGABAPENTINE ET SYNTHESE DE CE COMPOSE
  申请人：HIKAL LTD

  公开号：WO2005087709A1

  公开（公告）日：2005-09-22

  The present invention relates to compounds cis (Z) and trans (E) stereoisomers of 4-t-butylgapentin of formula (11) and (12) and a process for the preparation of the said stereoisomers.

  本发明涉及公式（11）和（12）的4-叔丁基加巴喷丁的顺式（Z）和反式（E）立体异构体化合物以及所述立体异构体的制备方法。
• Gabapentin analogues and process thereof
  申请人：Kuppuswamy Nagarajan

  公开号：US20050209332A1

  公开（公告）日：2005-09-22

  The present invention relates to compounds cis (Z) and trans (E) stereoisomers of 4-t-butylgabapentin of formula (11) and (12) and a process for the preparation of the said stereoisomers.

  本发明涉及化合物4-叔丁基加巴喷丁的顺式（Z）和反式（E）立体异构体，化学式为（11）和（12），以及制备所述立体异构体的方法。
• Spiropiperidine derivatives and their use as fungicides
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0621267A1

  公开（公告）日：1994-10-26

  The invention provides spiropiperidine derivatives of the general formula or an acid-addition salt thereof, in which R¹ represents a hydrogen atom or an optionally substituted alkyl, aryl or aralkyl group; R² represents a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl or heterocyclyl group; and either both groups X represent -CH₂- or both groups X represent -O-; processes for their preparation; compositions containing such compounds and their use as fungicides.

  这项发明提供了一般式的螺环哌啶衍生物或其酸盐加合物，其中R¹代表氢原子或可选择取代的烷基、芳基或芳基烷基；R²代表氢原子或可选择取代的烷基、烯基、炔基、环烷基、芳基、芳基烷基或杂环基；X代表-CH₂-的两个基团或X代表-O-的两个基团；它们的制备方法；含有这种化合物的组合物以及它们作为杀菌剂的用途。
• Cis (z) 4-t-butylgabapentin and its synthesis
  申请人：Hikal Limited

  公开号：EP2172445A1

  公开（公告）日：2010-04-07

  The present invention relates to compounds trans (E) and cis (Z) stereoisomers of 4-t-butylgabapentin of formula (11) and (12) and a process for the preparation of the said stereoisomers.

  本发明涉及式（11）和（12）的 4-叔丁基加巴喷丁的反式（E）和顺式（Z）立体异构体化合物，以及制备上述立体异构体的工艺。
• US5436343A
  申请人：——

  公开号：US5436343A

  公开（公告）日：1995-07-25