o-xylylenebis(malononitrile) | 199184-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: o-xylylenebis(malononitrile)
• 英文别名: 2-[[2-(2,2-Dicyanoethyl)phenyl]methyl]propanedinitrile；2-[[2-(2,2-dicyanoethyl)phenyl]methyl]propanedinitrile
• CAS: 199184-11-7
• 化学式: C₁₄H₁₀N₄
• 分子量: 234.26
• InChiKey: MBZZUYKIGLGIIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  己-4-炔-3-酮 、 o-xylylenebis(malononitrile) 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到(1RS,11SR)-14-ethyl-1-methyl-13-oxatricyclo[9.4.0.0^4,9]pentadeca-4,6,8,14-tetraen-12-one-2,2,11-tricarbonitrile
  参考文献：
  名称：

  Double Annulation Route to Fused Bicyclic Compounds with Three Contiguous Quaternary Centers

  摘要：

  Fused bicyclic and tricyclic compounds featuring two or three new C-C a bonds, two new rings, two or three new stereocenters, and three new contiguous quaternary centers can be prepared stereoselectively, atom economically, and in one synthetic operation via a cascade reaction of two nonstereogenic, readily available starting materials: a tethered bis(malononitrile) and an internal alkynone. The course of the "double annulation" changes drastically with the structure of the starting materials, alternately affording trans-decalins or cis-fused unsaturated lactones.

  DOI：

  10.1021/ol990935o
• 作为产物：
  描述：

  在 乙醇 、 氢气 作用下， 以3.30 g的产率得到o-xylylenebis(malononitrile)
  参考文献：
  名称：

  Double Annulation Route to Fused Bicyclic Compounds with Three Contiguous Quaternary Centers

  摘要：

  Fused bicyclic and tricyclic compounds featuring two or three new C-C a bonds, two new rings, two or three new stereocenters, and three new contiguous quaternary centers can be prepared stereoselectively, atom economically, and in one synthetic operation via a cascade reaction of two nonstereogenic, readily available starting materials: a tethered bis(malononitrile) and an internal alkynone. The course of the "double annulation" changes drastically with the structure of the starting materials, alternately affording trans-decalins or cis-fused unsaturated lactones.

  DOI：

  10.1021/ol990935o

文献信息

• Mono- vs. dialkylation of carbanions. Effects of absolute and relative acidity of the conjugate carbon acids in selectivity control
  作者：Luděk Ridvan、Jiří Závada

  DOI：10.1016/s0040-4020(97)00989-7

  日期：1997.10

  in the reaction of the dibromide 1 with carbanions 2a – 2g covering a range greater than 15 pK units in DMSO. It was found that the bis(monoalkylated) product 3 arises exclusively or predominantly from the carbanions 2d – 2g derived from the less acidic carbon acids 7d – 7g whereas the cyclic product of dialkylation 4 prevails in the reaction of the carbanions 2a – 2c derived from the more acidic carbon

  在二溴化物1与碳数2a-2g的反应中研究了标题问题，碳数2a-2g在DMSO中的作用范围大于15 pK单位。已发现，双（单烷基化）产物3完全或主要来自于较弱酸性碳酸7d – 7g产生的碳负离子2d – 2g，而二烷基化4的环状产物主要存在于衍生自其的碳负离子2a – 2c的反应中。酸性更高的碳酸7a – 7c。因此，烷基化选择性主要取决于参与反应的碳酸的绝对酸度。该小说的原理，以及在较早的研究基础上，根据等式提供了意外的发现。（1）–（4）。
• Double Annulation Route to Fused Bicyclic Compounds with Three Contiguous Quaternary Centers
  作者：Robert B. Grossman、Aaron J. Skaggs、Arlene E. Kray、Brian O. Patrick

  DOI：10.1021/ol990935o

  日期：1999.11.1

  Fused bicyclic and tricyclic compounds featuring two or three new C-C a bonds, two new rings, two or three new stereocenters, and three new contiguous quaternary centers can be prepared stereoselectively, atom economically, and in one synthetic operation via a cascade reaction of two nonstereogenic, readily available starting materials: a tethered bis(malononitrile) and an internal alkynone. The course of the "double annulation" changes drastically with the structure of the starting materials, alternately affording trans-decalins or cis-fused unsaturated lactones.