4,4 bis(2-methylpropyl)cyclohexanone | 130065-91-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4 bis(2-methylpropyl)cyclohexanone
• 英文别名: 4,4-Bis(2-methylpropyl)cyclohexan-1-one
• CAS: 130065-91-7
• 化学式: C₁₄H₂₆O
• 分子量: 210.36
• InChiKey: PPJQGTCZBZILHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4 bis(2-methylpropyl)cyclohexanone 在 乙酸铵 、 盐酸 、 lithium aluminium tetrahydride 、 水 、 乙酸酐 、 溶剂黄146 作用下， 以 乙醚 、 乙醇 、 水 、 甲苯 为溶剂， 反应 96.0h， 生成 [3-(8,8-Diisobutyl-2-aza-spiro[4.5]dec-2-yl)-propyl]-dimethyl-amine
  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：

  二异丁基酮 在 palladium on activated charcoal 硫酸 、 三氟化硼乙醚 、 氢气 、 sodium hydride 作用下， 以 二甲基亚砜 、 乙酸乙酯 、 苯 为溶剂， 5.0~70.0 ℃ 、344.73 kPa 条件下， 反应 20.02h， 生成 4,4 bis(2-methylpropyl)cyclohexanone
  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

• CHROMENE COMPOUND
  申请人：Izumi Shinobu

  公开号：US20140154527A1

  公开（公告）日：2014-06-05

  A chromene compound having a short fading half period, especially, a short fading half period even at a low temperature in a general-purpose polymer solid matrix. The chromene compound is represented by the following formula ( 1 ). wherein R 1 is a hydroxyl group or the like, R 2 and R 3 are each an aryl group or the like, C* is a spiro carbon atom, a spiro ring A represented by the following formula is a saturated hydrocarbon ring having 4 to 12 ring member carbon atoms or the like, and at least one ring member carbon atom constituting the ring A is a group represented by the following formula (4), and X is a divalent group such as arylene group, wherein R 7 and R 8 are each a cycloalkyl group or the like.

  具有短的褪色半衰期的香豆素化合物，特别是在通用聚合物固体基质中，即使在低温下也具有短的褪色半衰期。该香豆素化合物由以下式子（1）表示，其中R1为羟基或类似物，R2和R3分别为芳基或类似物，C*为螺碳原子，由以下式子表示的螺环A为具有4至12个环成员碳原子或类似物的饱和碳氢环，且构成环A的至少一个环成员碳原子为以下式子（4）所表示的基团，X为二价基团，例如芳基烷基，其中R7和R8分别为环烷基或类似物。
• Immunomodulatory azaspiranes
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0310321B1

  公开（公告）日：1994-11-30
• BADGER, ALISON M.;CHEESEMAN, ELAINE N.;DIMARTINO, MICHAEL J.;DORMAN, JAME+
  作者：BADGER, ALISON M.、CHEESEMAN, ELAINE N.、DIMARTINO, MICHAEL J.、DORMAN, JAME+

  DOI：——

  日期：——
• US9487693B2
  申请人：——

  公开号：US9487693B2

  公开（公告）日：2016-11-08
• [EN] IMMUNOMODULATORY AZASPIRANES
  申请人：——

  公开号：WO1989002889A1

  公开（公告）日：1989-04-06

  [FR] Sont décrits une composition pharmaceutique comprenant un support ou un diluant pharmaceutiquement acceptable ainsi qu'une quantité efficace d'un dérivé d'azaspirane, un procédé de traitement d'un animal nécessitant une immunomodulation, consistant à administrer audit animal une quantité efficace d'un dérivé d'azaspirane, et certains dérivés d'azaspirane.
  [EN] A pharmaceutical composition comprising a pharmaceutically acceptable carrier or diluent and an effective amount of an azaspirane derivative, a method of treating an animal in need of immunomodulation which comprises administering to such animal an effective amount of an azaspirane derivative, and certain azaspirane derivatives.