N,N'-dicyclopentylidenehydrazine | 20615-04-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-dicyclopentylidenehydrazine
• 英文别名: Cyclopentanonazin；1,2-dicyclopentylidenehydrazine；Cyclopentanone, cyclopentylidenehydrazone；N-(cyclopentylideneamino)cyclopentanimine
• CAS: 20615-04-7
• 化学式: C₁₀H₁₆N₂
• mdl: MFCD00462206
• 分子量: 164.25
• InChiKey: KFQDLKRAVRTKMF-UHFFFAOYSA-N

物化性质

• 熔点：
  25 °C
• 沸点：
  130-132 °C(Press: 22 Torr)
• 密度：
  1.0122 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  N,N'-dicyclopentylidenehydrazine 在 盐酸 、 1,2,3,4-四氢萘 作用下， 生成 2,3,4,5,6,7,8,9-八氢-1H-三茚
  参考文献：
  名称：

  Perkin; Plant, Journal of the Chemical Society, 1925, vol. 127, p. 1141

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊醇 在 Ru-MACHO 、 potassium tert-butylate 、 一水合肼 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以74%的产率得到N,N'-dicyclopentylidenehydrazine
  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

• Criss-cross Cycloadditions on Ketazines Derived from Alicyclic Ketones
  作者：Jiri Verner、Milan Potacek

  DOI：10.3390/11010034

  日期：——

  The reactivity of alicyclic ketazines in criss-cross cycloadditions was investigated. They react with potassium cyanate and ammonium thiocyanate in the presence of acetic acid to form spirocyclic perhydro[1,2,4]triazolo[1,2-alpha][1,2,4]triazole-1,5-diones and perhydro[1,2,4]triazolo[1,2-alpha][1,2,4]triazole-1,5-dithiones, respectively, in relatively high yields.

  研究了脂环族酮嗪在交叉环加成反应中的反应性。它们在乙酸存在下与氰酸钾和硫氰酸铵反应生成螺环全氢[1,2,4]三唑并[1,2-α][1,2,4]三唑-1,5-二酮和全氢[ 1,2,4]三唑并[1,2-α][1,2,4]三唑-1,5-二硫酮，分别以相对较高的产率。
• Studies on Isocyanides and Related Compounds; A Facile Synthesis of 4-Phenyl-1-(2H)phthalazinone-2-alkanoic Acid Amides
  作者：Stefano Marcaccini、Roberto Pepino、Cecilia Polo、M. Cruz Pozo

  DOI：10.1055/s-2001-9745

  日期：——

  A convenient synthesis of the title compounds by means of the Ugi four-component condensation (Ugi 4-CC) is reported. The reaction between acetaldehyde azine (3a), 2-benzoylbenzoic acid (4),and cyclohexyl isocyanide (5) spontaneously afforded N-cyclohexyl 2-(1,2-dihydro-1-oxo-4-phenylphthalazin-2-yl)propionamide (1a) upon loss of acetaldehyde from the intermediate Ugi 4-CC adduct 6a. Starting from the less reactive azines 3c-f arising from ketones, the Ugi 4-CC adducts 6c-f did not spontaneously cyclize, whereas phenylacetaldehyde azine (3b) afforded a mixture of the Ugi 4-CC adduct 6b and cyclized product 1b. In all of the cases, the adducts 6b-f were easily cyclized to 1b-f in acidic medium.

  报道了一种通过Ugi四组分缩合（Ugi 4-CC）方便合成标题化合物的方法。醛肟（3a）、苯乙酮（4）和环己基异氰酸酯（5）之间的反应在从中间Ugi 4-CC加合物6a中失去醛后，自发地生成了N-环己基2-(1,2-二氢-1-氧-4-苯基邻苯二甲酸酰胺（1a）。从由酮衍生的反应活性较低的肟（3c-f）出发，Ugi 4-CC加合物6c-f并未自发环化，而苯乙醛肟（3b）则生成了Ugi 4-CC加合物6b和环化产物1b的混合物。在所有情况下，加合物6b-f在酸性介质中都能容易地环化生成1b-f。
• Phthalocyanine-catalyzed hydrophosphorylation of hydrazones and azines
  作者：E. D. Matveeva、T. A. Podrugina、I. N. Kolesnikova、N. S. Zefirov

  DOI：10.1007/s11172-010-0114-3

  日期：2010.3

  Benzaldehyde, acetone, and N-Boc-piperidone phenylhydrazones, as well as azines derived from aromatic aldehydes and ketones, react with diethyl phosphite in the presence of [tetra(tert-butyl)phthalocyanine]aluminum chloride to give α-hydrazino phosphonates in high yields.

  苯甲醛、丙酮和 N-Boc-哌啶酮苯腙，以及衍生自芳香醛和酮的吖嗪，在 [四（叔丁基）酞菁] 氯化铝存在下与亚磷酸二乙酯反应，生成 α-肼基膦酸酯。产量。
• Process for producing azine compounds and oxime compounds
  申请人：——

  公开号：US20030204084A1

  公开（公告）日：2003-10-30

  A process comprising allowing a peroxide compound represented by following Formula (2): 1 wherein R a , R b , R c and R d are the same or different and are each a hydrogen atom or a hydrocarbon group, and wherein R a and R b , R c and R d may be combined to form a ring together with the adjacent carbon atom, respectively, to react with ammonia and water to yield an azine compound represented by following Formula (3): 2 wherein R a , R b , R c and R d have the same meanings as defined above, or oxime compounds represented by following Formulae (4 a ) and/or (4 b ): 3 wherein R a , R b , R c and R d have the same meanings as defined above, in the presence of a nitrogen-containing cyclic compound constitutively having a skeleton represented by following Formula (A) in its ring: 4 wherein X is one of an oxygen atom and an —OR group, and wherein R is one of a hydrogen atom and a hydroxyl-protecting group. This process can produce an oxime compound or an azine compound useful as a material for oxime compounds from low-cost materials by easy and simple procedures.

  一种过程包括允许由以下式（2）表示的过氧化物化合物：其中Ra、Rb、Rc和Rd相同或不同，每个都是氢原子或烃基，且Ra和Rb、Rc和Rd可以分别与相邻的碳原子结合形成环，以与氨和水反应生成由以下式（3）表示的偶氮化合物：其中Ra、Rb、Rc和Rd的含义与上述定义相同，或者在具有以下式（A）中的环中具有骨架的含氮环化合物的存在下生成由以下式（4a）和/或（4b）表示的肟化合物：其中Ra、Rb、Rc和Rd的含义与上述定义相同，在X为氧原子和-OR基团之一，R为氢原子和羟基保护基团之一的情况下。该过程可以通过简单易行的步骤从低成本材料中产生用作肟化合物材料的肟化合物或偶氮化合物。
• Reaction of singlet oxygen with azines: Implications for dioxirane intermediate
  作者：Wataru Ando、Rikiya Sato、Hideki Sonobe、Takeshi Akasaka

  DOI：10.1016/s0040-4039(01)80045-9

  日期：1984.1

  Photooxygenation of tricyclo[3.3.1.1]decanone azine (adamantanone azine) afforded, in addition to adamantanone, 4-oxahomoadamantan-5-one derived from a dioxirane intermediate via a non-radical pathway.

  除了金刚烷酮之外，三环[3.3.1.1]癸酮嗪（金刚烷酮嗪）的光氧化还提供了通过非自由基途径衍生自二环氧乙烷中间体的4-氧杂高锰金刚烷-5-酮。