4,4-diethyl-4-silacyclohexanone | 119996-87-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 4,4-diethyl-4-silacyclohexanone
• 英文别名: 1,1-diethyl-1-silacyclohexan-4-one；1,1-Diethylsilinan-4-one
• CAS: 119996-87-1
• 化学式: C₉H₁₈OSi
• 分子量: 170.327
• InChiKey: BBESLPVOFKVTTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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-diethyl-4-silacyclohexanone 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-Diethyl-2-aza-8-sila-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：

  1,1-二氯甲醚 、 1,1-diethyl-4-methoxy-1-sila-4-borinane 在 sodium hydroxide 、 双氧水 、 叔丁基锂 、 叔丁醇 作用下， 生成 4,4-diethyl-4-silacyclohexanone
  参考文献：
  名称：

  1-Silacyclohexan-4-ones and 1-germacyclohexan-4-ones: precursors to metalla-pharmaceuticals via boracycles

  摘要：

  DOI：

  10.1021/jo00271a046

文献信息

• SODERQUIST, JOHN E.;NEGRON, ALVIN, J. ORG. CHEM., 54,(1989) N0, C. 2462-2464
  作者：SODERQUIST, JOHN E.、NEGRON, ALVIN

  DOI：——

  日期：——