ethyl (4-t-butylcyclohexylidene)cyanoacetate | 22700-58-9

• 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: ethyl (4-t-butylcyclohexylidene)cyanoacetate
• CAS: 22700-58-9
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: VSBQQUAYJFHFJO-QBFSEMIESA-N

物化性质

• 沸点：
  177-180 °C(Press: 2 Torr)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.61
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl (4-t-butylcyclohexylidene)cyanoacetate 在 硫酸 作用下， 以 乙醚 为溶剂， 生成 Methyl trans-1-methyl-4-tert-butylcyclohexaneacetate
  参考文献：
  名称：

  Amsterdamsky,C. et al., Bulletin de la Societe Chimique de France, 1975, p. 635 - 643

  摘要：

  DOI：
• 作为产物：
  描述：

  4-叔丁基环己酮 、 氰乙酸乙酯 在 polystyrene-supported DABCO 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以93%的产率得到ethyl (4-t-butylcyclohexylidene)cyanoacetate
  参考文献：
  名称：

  聚苯乙烯固定的DABCO是Knoevenagel缩合反应的一种高效且可回收的有机催化剂†

  摘要：

  聚苯乙烯固定的DABCO首次用作碳-碳键形成反应的基本有机催化剂。负载型催化剂可在多种芳族/杂环/α，β-不饱和醛和酮与活性亚甲基化合物的Knoevenagel缩合反应中用作可重复使用的催化剂。反应条件温和并且该方法操作简单。反应在短时间内以100％的选择性进行。通过过滤可以容易地将催化剂与反应分离，并循环十次而没有活性损失。基于催化剂，还开发了一种连续流工艺。

  DOI：

  10.1039/c3ra43921f

文献信息

• Spiranes 6. Ring A homologues of N-benzyloxy-2-azaspiro[4.4]nonane-1,3-dione. Synthesis, X-ray analysis and anticonvulsant evaluation
  作者：MS Alexander、JP Stables、M Ciechanowicz-Rutkowska、MB Hursthouse、DE Hibbs、IO Edafiogho、VA Farrar、JA Moore、KR Scott

  DOI：10.1016/0223-5234(96)83972-9

  日期：——

  anticonvulsant activity. The study was designed to determine the effect of varying the carbocyclic (ring A) nucleus, while maintaining the heterocyclic ring constant, on anticonvulsant activity. Results indicate that maximum activity was obtained with the ring A comprised of a six-membered spiro ring system, 2a, one methylene group greater than that previously reported for N-(benzyloxy)-2-azaspiro[4

  合成了一系列螺琥珀酰亚胺，并评估了其抗惊厥活性。该研究旨在确定在维持杂环恒定的同时改变碳环（环A）核对抗惊厥活性的影响。结果表明，环A包含六元螺环系统2a，比先前报道的N-（苄氧基）-2-氮杂螺[4.4]壬烷-1,3-所报道的亚甲基大，获得的最大活性。 dione，1，原型类似物。化合物2a在MES测试中具有活性，并提供100 mg / kg的保护，螺十二烷类似物2g也是如此。X射线分析显示，活性2a和非活性螺辛烷类似物2f之间存在显着差异。但是，这些差异不能解释螺十二烷类似物2g表现出的意外活性。
• The stereoselective addition of organometallic reagents to electron-deficient alkylidenecyclohexanes; alternative linkages for cholaphane synthesis
  作者：Anthony P. Davis、Thomas J. Egan、Michael G. Orchard、Desmond Cunningham、Patrick McArdle

  DOI：10.1016/s0040-4020(01)89447-3

  日期：——

  Knoevenagel condensations between t-butylcyclohexanone and malononitrile, Meldrum's acid and ethyl cyanoacetate gave electron-deficient alkenes which underwent equatorial-selective attack by chemoselective aryl organometallic reagents. Further transformations of the products were shown to be possible in some cases. The methodology is relevant to the synthesis of macrocyclic “cholaphane” receptors with

  叔丁基环己酮和丙二腈，Meldrum的酸和氰基乙酸乙酯之间的Knoevenagel缩合产生了缺电子的烯烃，这些烯烃受到化学选择性芳基有机金属试剂的赤道选择性攻击。在某些情况下，可以对产品进行进一步的改造。该方法与具有外部定向的官能团的大环“胆烷”受体的合成有关。
• Nag, Ahindra; Sarkar, Ashis; Sarkar, Samir K., Synthetic Communications, 1987, vol. 17, # 8, p. 1007 - 1014
  作者：Nag, Ahindra、Sarkar, Ashis、Sarkar, Samir K.、Palit, Sunanda K.

  DOI：——

  日期：——
• Antiarthritic and supressor cell inducing activity of azaspiranes: structure-function relationships of a novel class of immunomodulatory agents
  作者：Alison M. Badger、David A. Schwartz、Donald H. Picker、James W. Dorman、Fontaine C. Bradley、Elaine N. Cheeseman、Michael J. DiMartino、Nabil Hanna、Christopher K. Mirabelli

  DOI：10.1021/jm00173a010

  日期：1990.11

  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.
• Stereochemical aspects of the Claisen rearrangement of allyl vinyl ethers
  作者：Herbert O. House、Jacek Lubinkowski、James J. Good

  DOI：10.1021/jo00889a019

  日期：1975.1