4-methylcyclohexane-1,1-diacetic acid anhydride | 85179-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-methylcyclohexane-1,1-diacetic acid anhydride
• 英文别名: (4-methyl-cyclohexane-1,1-diyl)-di-acetic acid-anhydride；(4-Methyl-cyclohexan-1,1-diyl)-di-essigsaeure-anhydrid；9-Methyl-3-oxaspiro[5.5]undecane-2,4-dione
• CAS: 85179-92-6
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: NVUHONMDCICFLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methylcyclohexane-1,1-diacetic acid anhydride 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 dimethyl-[3-(9-methyl-3-aza-spiro[5.5]undec-3-yl)-propyl]-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：

  4-甲基环己酮 在 盐酸 、 硫酸 、 氨 、 水 、 乙酸酐 作用下， 反应 24.0h， 生成 4-methylcyclohexane-1,1-diacetic acid anhydride
  参考文献：
  名称：

  评价各种N-取代的氮杂螺环二酮衍生物作为潜在的抗菌剂

  摘要：

  将一系列的N-取代的肼与各种螺[4.5]和[5.5]酸酐缩合，并评估所得的N-取代的氮杂氮杂双阴离子的抗菌活性。在测试的各种生物中，没有一个显示出明显的活性。

  DOI：

  10.1002/jps.2600720222

文献信息

• Evaluation of Various N-Substituted Azaspiranedione Derivatives as Potential Antimicrobial Agents
  作者：K.R. Scott、Poledi G. Kennedy、Murray Kemp、Vasant G. Telang、H.W. Matthews

  DOI：10.1002/jps.2600720222

  日期：1983.2

  A series of N-substituted hydrazines were condensed with various spiro[4.5] and [5.5] anhydrides and the resultant N-substituted azaspiranediones were evaluated for antimicrobial activity. None displayed any significant activity in a variety of organisms tested.

  将一系列的N-取代的肼与各种螺[4.5]和[5.5]酸酐缩合，并评估所得的N-取代的氮杂氮杂双阴离子的抗菌活性。在测试的各种生物中，没有一个显示出明显的活性。
• Thorpe; Wood, Journal of the Chemical Society, 1913, vol. 103, p. 1575
  作者：Thorpe、Wood

  DOI：——

  日期：——
• Mathur,K.C.; Saharia,G.S., Indian Journal of Chemistry, 1964, vol. 2, p. 358 - 360
  作者：Mathur,K.C.、Saharia,G.S.

  DOI：——

  日期：——
• Sen Gupta,S.C.; Sen,P.K., Journal of the Indian Chemical Society, 1962, vol. 39, p. 815 - 822
  作者：Sen Gupta,S.C.、Sen,P.K.

  DOI：——

  日期：——
• SCOTT, K. R.;KENNEDY, P. G.;KEMP, M.;TELANG, V. G.;MATTHEWS, H. W., J. PHARM. SCI., 1983, 72, N 2, 183-186
  作者：SCOTT, K. R.、KENNEDY, P. G.、KEMP, M.、TELANG, V. G.、MATTHEWS, H. W.

  DOI：——

  日期：——