4-Heptanone azine | 92326-42-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-Heptanone azine
• 英文别名: tetrapropylazine；1,2-di(heptan-4-ylidene)hydrazine；Dipropylketazin；Di-n-propyl-ketazin；bis-(1-propyl-butylidene)-hydrazine；Bis-(1-propyl-butyliden)-hydrazin；heptan-4-one azine；heptan-4-on-azine；Heptan-4-on-azin；Butyronazin；N-(heptan-4-ylideneamino)heptan-4-imine
• CAS: 92326-42-6
• 化学式: C₁₄H₂₈N₂
• 分子量: 224.39
• InChiKey: PFSTVHYGWWMKLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  188 °C
• 密度：
  0.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Heptanone azine 在 氢气 、 镍 作用下， 生成 4-氨基庚烷
  参考文献：
  名称：

  Mailhe, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1920, vol. 170, p. 1265

  摘要：

  DOI：
• 作为产物：
  描述：

  4-庚醇 在 Ru-MACHO 、 potassium tert-butylate 、 一水合肼 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以84%的产率得到4-Heptanone azine
  参考文献：
  名称：

  钌（ii）催化的仲醇直接合成酮嗪†

  摘要：

  据报道，由钌夹钳络合物催化仲醇直接从仲醇和水合肼中直接合成氯胺酮，该过程是通过仲醇通过胺-酰胺金属-配体在催化剂中的协同作用进行O-H键活化而进行的。值得注意的是，释放出的分子氢和水是唯一的副产物。

  DOI：

  10.1039/c9cc01383k

文献信息

• Photolysis of dipropyldiazirine and trapping of dipropylcarbene with piperidine
  作者：Eunju Lee Tae、Matthew S Platz

  DOI：10.1016/s0040-4039(99)00356-1

  日期：1999.4

  pathway involves dipropylcarbene formed directly from the diazirine, the other pathways are attributed to ionic and photochemical reactions of 4-diazoheptane and to the excited state of the diazirine precursor. Dipropylcarbene can be easily intercepted with a simple trap. The yield of this process is limited by the efficiency with which the precursor forms the carbene.

  二丙基二嗪在二氯甲烷中于4°C进行的光解（350 nm）产生E和Z 3-庚烯的混合物，产率为81％，比率为1.8。形成的四丙嗪的产率低于5％。在哌啶存在下二丙基二嗪碱的光解导致形成卡宾-胺加合物。在0.06 M哌啶的存在下，加合物的收率为48％，E和Z 3-庚烯的收率为47％，而3-庚烯的比例为1.1。结果表明，庚烯是由三个途径形成的。一个途径涉及直接由二嗪生成的二丙基卡宾，其他途径归因于4-重氮庚烷的离子和光化学反应以及归二嗪前体的激发态。用一个简单的捕集阱可以很容易地截获二丙基卡宾。该方法的产率受到前体形成卡宾的效率的限制。
• Miyatake, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1953, vol. 73, p. 460,462
  作者：Miyatake

  DOI：——

  日期：——
• Mailhe, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1920, vol. 170, p. 1265
  作者：Mailhe

  DOI：——

  日期：——
• Kauffmann,T.; Berger,D., Chemische Berichte, 1968, vol. 101, p. 3022 - 3030
  作者：Kauffmann,T.、Berger,D.

  DOI：——

  日期：——
• Chemistry and Kinetics of Dipropylcarbene in Solution
  作者：Eunju Lee Tae、Zhendong Zhu、Matthew S. Platz、John Paul Pezacki、John Warkentin

  DOI：10.1021/jp990198d

  日期：1999.7.1

  The photochemistry of 2-methoxy-2-methyl-5,5-dipropyl-Delta(3)-1,3,4-oxadiazoline (1a) and 2,2-dimethoxy-5,5-dipropyl-Delta(3)-1,3,4-oxadiazoline (1b) was investigated. Photolysis (300 nm) of these compounds in solution leads to fragmentation to 4-diazoheptane (major), which slowly forms the corresponding azine. Fragmentation to form 4-heptanone is also observed. Yields of 4-diazoheptane in CH2Cl2 are much larger than those in pentane. 4-Diazoheptane can be trapped with 1-pentene to form a pyrazoline or with methanol to form 4-methoxyheptane. The pyrazoline can be decomposed photochemically to form 1,1,2-tripropylcyclopropane. In solution, 4-diazoheptane is inefficiently photolyzed to dipropylcarbene (DPC), which can be trapped with piperidine or with pyridine in laser flash photolysis experiments. Analysis of the piperidine and pyridine data indicates that the lifetime of DPC in cyclohexane, methylene chloride, or Freon-113 (CF2ClCFCl2) solution at ambient temperature is controlled by 1,2 hydrogen migration to form Z- and E-3-heptene. The lifetime deduced under these conditions is approximate to 300 ps, which is about 20-fold shorter than that of dimethylcarbene in perfluorohexane at ambient temperature. Upon photolysis (254 nm) of oxadiazoline 1a in argon, 4-diazoheptane and 1-methoxydiazoethane are formed. These diazo compounds undergo subsequent photolysis that revealed the formation of methoxy(methyl)carbene and E- and Z-3-heptene. It was not possible to detect DPC in argon at 14 K.