3-Methoxy-4-cyclohexen-1,1,2,2-tetracarbonitril | 74503-37-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-Methoxy-4-cyclohexen-1,1,2,2-tetracarbonitril
• 英文别名: 3-Methoxy-4.4.5.5-tetracyano-1-cyclohexen；3-methoxycyclohex-4-ene-1,1,2,2-tetracarbonitrile
• CAS: 74503-37-0
• 化学式: C₁₁H₈N₄O
• 分子量: 212.211
• InChiKey: LYBHUZXLDCJNBU-UHFFFAOYSA-N

物化性质

• 沸点：
  532.1±50.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  104.39
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-cis-Methoxy-1,3-trans-butadiene 、 四氰基乙烯 以 二氯甲烷 为溶剂， 以86%的产率得到3-Methoxy-4-cyclohexen-1,1,2,2-tetracarbonitril
  参考文献：
  名称：

  Ruecker, Christa; Lang, Dietrich; Sauer, Juergen, Chemische Berichte, 1980, vol. 113, # 5, p. 1663 - 1690

  摘要：

  DOI：

文献信息

• a(<i>E</i>)-1-Methoxy-1,3-butadiene and 1,1-Dimethoxy-1,3-butadiene in (4 + 2) Cycloadditions. A Mechanistic Comparison
  作者：Reiner Sustmann、Surajin Tappanchai、Heinz Bandmann

  DOI：10.1021/ja961390l

  日期：1996.1.1

  The reactions of (E)-1-methoxy-1,3-butadiene (1) and 1,1-dimethoxy-1,3-butadiene (2) with a series of dienophiles of increasing electrophilicity are described Stereochemical studies reveal that the cycloadditions of 1 are concerted processes, even for the most electron-deficient olefins dimethyl dicyanofumarate and dimethyl dicyanomaleate. 1,1-Dimethoxy-1,3-butadiene reacts under our conditions (dilute solutions and temperatures less than or equal to 60 degrees C) only with those dienophiles which can give zwitterions out of the antiperiplanar conformation of the diene. Zwitterionic intermediates can be trapped by methanol. In the case of tetracyanoethene the kinetics of decay of an intermediate, interpreted as the zwitterion, can be followed by stopped flow techniques: E(a) = 14.8 +/- 0.2 kcal mol(-1), log A = 11.9 +/- 0.1, Delta H double dagger = 10.8 +/- 0.1 kcal mol(-1), Delta S double dagger = -6.2 +/- 0.1 cal mol(-1) K-1, and Delta G double dagger = 11.40 +/- 0.03 kcal mol(-1).
• <b>Cyanocarbon Chemistry. XIX.^1,2 Tetracyanocyclobutanes from Tetracyanoethylene and Electron-rich Alkenes</b>
  作者：J. K. Williams、D. W. Wiley、B. C. McKusick

  DOI：10.1021/ja00870a037

  日期：1962.6
• HIRANUMA, HIDETOSHI;MILLER, S. I., J. ORG. CHEM., 1982, 47, N 26, 5083-5088
  作者：HIRANUMA, HIDETOSHI、MILLER, S. I.

  DOI：——

  日期：——