diethyl (1E,2E)-cyclohexane-1,2-diylidenediacetate | 64566-40-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl (1E,2E)-cyclohexane-1,2-diylidenediacetate
• 英文别名: (E,E)-1,2-Bis(ethoxycarbonylmethylene)cyclohexane；bis(ethoxycarbonylmethylene)cyclohexane；ethyl (2E)-2-[(2E)-2-(2-ethoxy-2-oxoethylidene)cyclohexylidene]acetate
• CAS: 64566-40-1
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: SREAMHWNAYIWJB-WGDLNXRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  diethyl deca-2,8-diyn-1,10-dioate 在 四(三苯基膦)镍 作用下， 以 四氢呋喃 为溶剂， 以8%的产率得到diethyl (1E,2E)-cyclohexane-1,2-diylidenediacetate
  参考文献：
  名称：

  Nickel(0)-promoted synthesis of tetralin lactones from the co-cyclisation of monoynes and octa-1,7-diynes terminally substituted with ester or amide groups

  摘要：

  The co-cyclisation of octa-1,7-diynes with a variety of monoynes mediated by nickel(0) requires ester or amide groups at the terminal positions of the diyne and is subject to steric hindrance about the diyne rather than the monoyne; fused tetralin lactones are the most common products obtained in moderate to good yields. Intramolecular cyclisation of two triynes to the same type of product gives superior yields.

  DOI：

  10.1039/p19920002163

文献信息

• Nickel(0)-Catalyzed Dimerization of Ethyl Cyclopropylideneacetates
  作者：Taishi Kawasaki、Shinichi Saito、Yoshinori Yamamoto

  DOI：10.1021/jo0255678

  日期：2002.7.1

  The dimerization of ethyl cyclopropylideneacetates proceeded in the presence of Ni(0) catalysts, and cyclic compounds or linear compounds were formed in selective manners. The structures of products were highly dependent on the structure of the substrate and the ligands bound to the catalyst. The mechanism of the reactions was discussed in detail.

  在Ni（0）催化剂存在下进行环亚丙基乙酸乙酯的二聚反应，并以选择性方式形成环状化合物或线性化合物。产品的结构高度依赖于底物的结构以及与催化剂结合的配体。详细讨论了反应机理。
• A Convenient Method for the Synthesis of 2,5-Difunctionalized Phospholes Bearing Ester Groups
  作者：Yoshihiro Matano、Tooru Miyajima、Takashi Nakabuchi、Yuichiro Matsutani、Hiroshi Imahori

  DOI：10.1021/jo0605748

  日期：2006.7.1

  Symmetrically and unsymmetrically 2,5-difunctionalized phospholes bearing ester groups were prepared in a one-pot procedure from the corresponding diynes and dichloro-(phenyl) phosphine via titanacyclopentadienes. The observed optical properties of the functionalized phospholes show that the pi-conjugative push-pull interaction between the 2- and 5-substituents plays an important role in controlling the light-emitting efficiency.
• [3 + 3] Cyclodimerization of Methylenecyclopropanes: Stoichiometric and Catalytic Reactions of Nickel(0) with Electron-Deficient Alkylidenecyclopropanes
  作者：Masato Ohashi、Tomoaki Taniguchi、Sensuke Ogoshi

  DOI：10.1021/om100317y

  日期：2010.6.14

  Stoichiometric treatment of Ni(cod)(2) with ethyl cyclopropylideneacetate (ECPA) in the presence of PCy3 resulted in an unpredicted formation of a Ni(0) complex bearing an (E,E)-1,2-bis(exo-alkylidene)cyclohexane ligand, which stemmed from the [3 + 3] cyclodimerization of ECPA. The reaction could be expanded to a Ni(0)-catalyzed [3 + 3] cyclodimerization reaction of ester-substituted methylenecyclopropanes, giving the corresponding cyclohexane derivatives in excellent yields.
• TAYLOR R. J. K., SYNTHESIS, 1977, NO 8, 564-565
  作者：TAYLOR R. J. K.

  DOI：——

  日期：——
• Nickel(0)-promoted synthesis of tetralin lactones from the co-cyclisation of monoynes and octa-1,7-diynes terminally substituted with ester or amide groups
  作者：Parveen Bhatarah、Edward H. Smith

  DOI：10.1039/p19920002163

  日期：——

  The co-cyclisation of octa-1,7-diynes with a variety of monoynes mediated by nickel(0) requires ester or amide groups at the terminal positions of the diyne and is subject to steric hindrance about the diyne rather than the monoyne; fused tetralin lactones are the most common products obtained in moderate to good yields. Intramolecular cyclisation of two triynes to the same type of product gives superior yields.