3-methyl-3-cyanocyclopropene | 85523-25-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-methyl-3-cyanocyclopropene
• 英文别名: Cyclopropene-3-carbonitrile, 1-methyl-；1-methylcycloprop-2-ene-1-carbonitrile
• CAS: 85523-25-7
• 化学式: C₅H₅N
• 分子量: 79.1014
• InChiKey: XYSZFWTYCDPXEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  47 °C(Press: 30 Torr)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-3-cyanocyclopropene 在 萘烷 作用下， 反应 5.0h， 以70%的产率得到3-methyl-2,3-bis(2-methyl-2-cyanocyclopropyl)-1-(2-methyl-2,3-dicyanocyclopropyl)cyclopropene
  参考文献：
  名称：

  Tetramerization of 3-Methyl-cyclopropene-3-carbonitrile: A Novel CN-Alder-ene Reaction

  摘要：

  At elevated temperatures 3-methyl-cyclopropene-3-carbonitrile I was found to tetramerize giving compound 2 (3-methyl-2,3-bis(2-t-methyl-2-c-eyanocyclopropyl)- 1-(2-t-methyl-2-c,3-c-dicyanocyclopropyl)-cyclopropene) in good yields. This is the first example of Alder-ene type oligomerization of a 3,3-disubstituted cyclopropene. On the basis of the product geometry and stereoselective character of the reaction, a mechanism of formation of 2 involving CN-Alder-ene reaction was proposed. DFT modeling of the mechanism has shown that the CN-Alder-ene reaction is possible as a stepwise process involving a biradical intermediate.

  DOI：

  10.1021/jo8005254
• 作为产物：
  描述：

  8-methyl-tetrazolo[1,5-b]pyridazine 以 二氯甲烷 为溶剂， 生成 3-methyl-3-cyanocyclopropene
  参考文献：
  名称：

  Photochemistry. X. Photolysis of Tetrazolo [1, 5-b] pyridazines

  摘要：

  研究了 3-叠氮哒嗪，即四唑并 [1, 5-b] 哒嗪（I）的光解作用。未取代和甲基取代的化合物（Ia-d）生成了 3-氰基环丙烯（III）。另一方面，6-甲氧基化合物（Ie）产生了三烯（IV）和乙烯（V 和 VI）。这些化合物被认为是通过重氮中间体 (VIII) 和碳烯 (X) 形成的。

  DOI：

  10.1248/cpb.21.2517

文献信息

• Diels-Alder modification of monoterpenes and Alder-ene synthesis involving 3-methyl-3-cyanocyclopropene
  作者：R. V. Ashirov、S. A. Appolonova、V. V. Plemenkov

  DOI：10.1007/s10600-006-0174-7

  日期：2006.7

  Monoterpene derivatives with a cyclopropane moiety in the molecule were prepared by reactions of 3-methyl-3-cyanocyclopropene with several monoterpenes and terpenoids (β-myrcene, neoalloocimene, alloocimene, β-pinene, carvone). They were formed using the Diels-Alder reaction, Alder-ene synthesis, conjugated Alder-ene addition, and Diels-Alder cyclization.

  分子中带有环丙烷部分的单萜衍生物是通过 3-甲基-3-氰基环丙烯与几种单萜和萜类化合物（β-月桂烯、新别罗勒烯、别罗勒烯、β-蒎烯、香芹酮）反应制备的。它们是通过狄尔斯-阿尔德反应、阿尔德烯合成、共轭阿尔德烯加成和狄尔斯-阿尔德环化形成的。
• Bolesov, I. G.; Ignatchenko, A. V.; Bovin, N. V., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 1.2, p. 87 - 100
  作者：Bolesov, I. G.、Ignatchenko, A. V.、Bovin, N. V.、Prudchenko, I. A.、Surmina, L. S.、et al.

  DOI：——

  日期：——
• Latypova, M. M.; Plemenkov, V. V.; Kalinina, V. N., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 489 - 495
  作者：Latypova, M. M.、Plemenkov, V. V.、Kalinina, V. N.、Bolesov, I. G.

  DOI：——

  日期：——
• Rul'; Plemenkov; Gubaidullin, Russian Journal of Organic Chemistry, 1999, vol. 35, # 8, p. 1121 - 1126
  作者：Rul'、Plemenkov、Gubaidullin、Litvinov、Kataeva、Apollonova

  DOI：——

  日期：——
• Gritsenko, E. I.; Khaliullin, R. R.; Plemenkov, V. V., Journal of general chemistry of the USSR, 1988, vol. 58, # 12, p. 2433 - 2436
  作者：Gritsenko, E. I.、Khaliullin, R. R.、Plemenkov, V. V.、Faizullin, E. M.

  DOI：——

  日期：——