6-phenyl-1,5-diazabicyclo[3.1.0]hexane | 245415-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-phenyl-1,5-diazabicyclo[3.1.0]hexane
• CAS: 245415-92-3
• 化学式: C₁₀H₁₂N₂
• mdl: MFCD02197702
• 分子量: 160.219
• InChiKey: RDVKGBAGAJEUAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-phenyl-1,5-diazabicyclo[3.1.0]hexane 在 zinc trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 以87 %的产率得到1-benzyl-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  氧化还原中性锌催化级联 [1,4]-H 移位/二氮丙啶与供体-受体氮丙啶环化

  摘要：

  使用锌催化实现二氮丙啶与供体-受体氮丙啶 (DAA) 的偶联，通过[1,4]-氢化物转移提供咪唑并吡唑-4,4-二羧酸酯。锌催化、[1,4]-氢化物变换、天然产物修饰和后期分子对接研究的使用是重要的实用特征。

  DOI：

  10.1039/d4cc00226a
• 作为产物：
  描述：

  苯甲醛 、 N-chlorotrimethylenediamine 以 甲醇 为溶剂， 反应 24.0h， 生成 6-phenyl-1,5-diazabicyclo[3.1.0]hexane
  参考文献：
  名称：

  摘要：

  A new method was developed for the synthesis of 6-substituted 1,5-diazabicyclo[3.1.0]hexanes and 7-substituted 1,6-diazabicyclo[4.1.0]heptanes by condensation of N-monohalotrimethylene- and N-monohalotetramethylenediamines with carbonyl compounds in the presence of bases. X-ray diffraction studies and quantum-chemical B3LYP/6-31G* calculations demonstrated that the conformations of the resulting bicyclic systems are stabilized by stereoelectronic interactions. As a result, a boat conformation prevails in 1,5-diazabicyclo[3. 1.0]hexanes, whereas the energies of chair, half-chair, and boat conformations of 1,6-diazabicyclo[4.1.0]heptanes are equalized.

  DOI：

  10.1023/a:1023962907733

文献信息

• Chiral Sc^III–<i>N</i>,<i>N</i>′-Dioxide-Catalyzed 1,3-Dipolar Cycloaddition of Diaziridines with Chalcones
  作者：Haipeng Hu、Jinxiu Xu、Fang Wang、Shunxi Dong、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/acs.orglett.9b04007

  日期：2020.1.3

  enantioselective 1,3-dipolar cycloaddition of meso-diaziridines with chalcones was realized by utilizing the ScIII-N,N'-dioxide complex as the catalyst. In this transformation, the 1,3-dipole intermediates generated from the C-N bond cleavage of diaziridine were trapped by chiral N,N'-dioxide/scandium(III) complex activated chalcones to undergo enantioselective 1,3-dipolar cycloaddition. A range of chiral

  通过使用ScIII-N，N'-二氧化物络合物作为催化剂，实现了介孔二氮丙啶与查耳酮的高度对映选择性1,3-偶极环加成反应。在该转化中，由手性N，N′-二氧化物/ scan（III）络合物活化的查耳酮捕获由重氮丙啶的CN键裂解产生的1，3-偶极中间体，进行对映选择性的1，3-偶极环加成。可以容易地以高收率合成具有高非对映选择性和对映选择性的一系列手性1,5-二氮杂双[3.3.0]辛烷衍生物。
• (3+3)-Annulation of Donor-Acceptor Cyclopropanes with Diaziridines
  作者：Alexey O. Chagarovskiy、Vladimir S. Vasin、Vladimir V. Kuznetsov、Olga A. Ivanova、Victor B. Rybakov、Alexey N. Shumsky、Nina N. Makhova、Igor V. Trushkov

  DOI：10.1002/anie.201805258

  日期：2018.8.6

  The first example of (3+3)‐annulation of two different three‐membered rings is reported herein. Donor‐acceptor cyclopropanes in reaction with diaziridines were found to afford perhydropyridazine derivatives in high yields and diastereoselectivity under mild Lewis acid catalysis. The disclosed reaction is applicable for the broad substrate scope and exhibits an excellent functional group tolerance.

  本文报道了两个不同的三元环的（3 + 3）环的第一个示例。发现供体-受体环丙烷与二氮丙啶反应可在温和的路易斯酸催化下以高收率和非对映选择性提供全氢哒嗪衍生物。所公开的反应适用于广泛的底物范围并且表现出优异的官能团耐受性。
• Expedient iron-catalyzed stereospecific synthesis of triazines <i>via</i> cycloaddition of aziridines with diaziridines
  作者：Tanumay Sarkar、Kangkan Talukdar、Subhasish Roy、Tharmalingam Punniyamurthy

  DOI：10.1039/c9cc10089j

  日期：——

  Iron-catalyzed stereospecific [3+3]-annulation of aziridines with diaziridines is described to furnish [1,2,4]-triazines in high yield at room temperature. The use of an inexpensive iron salt catalyst, substrate scope and enantiomeric purity are the important practical features.

  描述了铁催化的氮丙啶与二氮丙啶的立体特异性[3 + 3]-环化反应可在室温下高产率地提供[1,2,4]-三嗪。廉价的铁盐催化剂的使用，底物范围和对映体纯度是重要的实用特征。
• Double Addition of Diphenylcyclopropenone to Azomethine Imines Generated from 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes
  作者：Alexander P. Molchanov、Denis I. Sipkin、Yuri B. Koptelov、Rafael R. Kostikov

  DOI：10.1002/1099-0690(20022)2002:3<453::aid-ejoc453>3.0.co;2-r

  日期：2002.2

  thermolysis conditions presumably occurs via the initially formed unstable dipolar bicyclic intermediates 4. Isomerization of these intermediates and subsequent addition of the second molecule of diphenylcyclopropenone with the extrusion of one molecule of carbon monoxide results in the formation of tricyclic 4a,7b-diazacyclopenta[cd]inden-7-ones 8 in good yields.

  在热解条件下，由6-芳基-1,5-二氮杂双环[3.1.0]己烷1生成的偶氮甲亚胺与二甲环亚胺形成的二倍过量的二苯基环丙烯酮的正式[2 + 3]环加成反应可能是通过最初形成的不稳定的偶极双环中间体4发生的。这些中间体的异构化以及随后的第二分子二苯基环丙烯酮的加入以及一分子一氧化碳的挤出导致以良好的产率形成三环的4a，7b-二氮杂环戊[ cd ]茚满7-酮8。
• Thermally Induced Tandem Cycloaddition of 2-Alkyl-3-phenylcyclopropenones to 6-Aryl-1,5-diazabicyclo[3.1.0]hexanes
  作者：A. P. Molchanov、D. I. Sipkin、Yu. B. Koptelov、R. R. Kostikov

  DOI：10.1007/s11178-005-0205-z

  日期：2005.4

  Thermolysis of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes in the presence of 2-alkyl-3-phenylcyclopropenones gives fused polycyclic systems of the 4a,7b-diazacyclopenta[cd]inden-7-one series as a result of addition of two cyclopropenone molecules and extrusion of CO molecule. The first step of the process is characterized by 100% regioselectivity, leading to the adduct with vicinal arrangement of the aryl groups, while the regioselectivity of the second step is likely to be determined by spatial interactions between substituents in the cyclopropenone molecule and trimethylene bridge of the diazabicyclohexane. Steric hindrances in the second step could eliminate formation of stable products.

  6- 芳基-1,5-二氮杂双环[3.1.0]己烷在 2-烷基-3-苯基环丙烯酮存在下发生热解，产生 4a,7b-二氮杂环戊并[cd]茚-7-酮系列的融合多环体系，这是两个环丙烯酮分子相加和 CO 分子挤出的结果。该过程第一步的特点是具有 100% 的区域选择性，可产生芳基邻接排列的加合物，而第二步的区域选择性可能取决于环丙烯酮分子中的取代基和二氮杂双环己烷的三亚甲基桥之间的空间相互作用。第二步中的立体阻碍可能会导致无法形成稳定的产物。