1,2,3,7b-tetrahydro-1,1a-diazacyclopropa[a]naphthalene | 92658-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1,2,3,7b-tetrahydro-1,1a-diazacyclopropa[a]naphthalene
• 英文别名: 1,2,3,7b-tetrahydro-1,1a-diazacyclopropa[α]naphthalene；1,2-Diaziridino-Py-tetrahydro-isochinolin；1,3,4,8b-tetrahydro[1,2]diazireno[3,1-a]isoquinoline；1,3,4,8b-tetrahydro-diazirino[3,1-a]isoquinoline；1,3,4,8b-Tetrahydrodiazirino[3,1-a]isoquinoline；1,3,4,8b-tetrahydrodiazirino[3,1-a]isoquinoline
• CAS: 92658-37-2
• 化学式: C₉H₁₀N₂
• 分子量: 146.192
• InChiKey: BJMXPXPSUYUTIM-UHFFFAOYSA-N

物化性质

• 熔点：
  93-95 °C(Solv: ethanol (64-17-5))
• 沸点：
  244.1±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,7b-tetrahydro-1,1a-diazacyclopropa[a]naphthalene 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.5h， 生成 3-methyl-4,5-dihydro-3H-benzo[d][1,2]diazepine
  参考文献：
  名称：

  Synthesis and characterization of a diaziridinium ion. Conversion of 3,4-dihydroisoquinolines to 4,5-dihydro-3H-benzo[2,3]diazepines via a formal N-insertion process

  摘要：

  DOI：

  10.1016/j.tet.2014.03.015
• 作为产物：
  描述：

  四氢异喹啉 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 hydroxylamine-O-sulfonic acid 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1,2,3,7b-tetrahydro-1,1a-diazacyclopropa[a]naphthalene
  参考文献：
  名称：

  C，N-环偶氮亚胺亚胺与烯丙基烷基酮的1,3-偶极环加成反应不对称合成四氢异喹啉衍生物

  摘要：

  [3 + 2]已实现C，N-环甲亚胺亚胺与烯丙基烷基酮的1,3-偶极环加成反应。反应在温和的条件下进行，并能耐受各种官能团。通常以良好的非对映选择性和对映选择性（高达> 25：1 dr，> 95％ee）构造一系列四氢异喹啉衍生物。此外，事先通过使用量子电子圆二色性计算和ECD光谱法确定了产物的绝对构型。

  DOI：

  10.3390/molecules26102969

文献信息

• Facile Regioselective Synthesis of Pyrazolo[5,1-<i>a</i>]isoquinolines via Ring-Opening Cyclization/Oxidation Reactions of Stable Aroyldiaziridines of 3,4-Tetrahydroisoquinoline with Alkynes
  作者：Howard Alper、Heriberto Ortega、Sara Ahmed

  DOI：10.1055/s-2007-990888

  日期：2007.12

  4-tetrahydroisoquinolines undergo regioselective cycloaddition reactions with a number of both mono and disubstituted alkynes, affording five-membered ring products which, after oxidative aromatization of the pyrazoline ring, lead to the efficient preparation of pyrazolo[5,1-a]isoquinolines. The overall transformation is base-catalyzed and occurs more rapidly in the presence of oxygen, in halogenated

  :: 新制备的稳定的 3,4-四氢异喹啉的芳酰基二氮丙啶与许多单取代和双取代炔烃发生区域选择性环加成反应，得到五元环产物，在吡唑啉环氧化芳构化后，可有效制备吡唑啉[5,1-a]异喹啉。整个转化是碱催化的，在有氧、卤化溶剂和二恶烷的情况下发生得更快。
• Stable azomethine imines having a 3,4-dihydroisoquinoline fragment and their cycloaddition to N-arylmaleimides
  作者：Yu. B. Koptelov、S. P. Saik、A. P. Molchanov

  DOI：10.1134/s1070428011040129

  日期：2011.4

  Aroylation of 5,6,8,8a,13,14,16,16a-octahydro[1,2,4,5]tetrazino[6,1-a:3,4-a']diisoquinoline or 1,3,4,8b-tetrahydro[1,2]diazireno[3,1-a]isoquinoline, as well as reactions of 2-(2-bromoethyl)benzaldehyde with aroylhydrazines followed by treatment with triethylamine, led to the formation of stable azomethine imines, aroyl(3,4-dihydroisoquinolinium-2-yl)azanides. 1,3-Dipolar cycloaddition of the latter to N-mesitylmaleimide was stereoselective: the ratio of the trans- and cis-adducts was similar to(3-7): 1, the former prevailing. The reactions with N-arylmaleimides having no ortho-substituents in the aryl group gave the corresponding cis-adducts as the major products [trans/cis ratio similar to 1: (2.5-10)].
• Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones
  作者：Guipeng Feng、Guoyang Ma、Wenyan Chen、Shaohong Xu、Kaikai Wang、Shaoyan Wang

  DOI：10.3390/molecules26102969

  日期：——

  [3 + 2] A 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of

  [3 + 2]已实现C，N-环甲亚胺亚胺与烯丙基烷基酮的1,3-偶极环加成反应。反应在温和的条件下进行，并能耐受各种官能团。通常以良好的非对映选择性和对映选择性（高达> 25：1 dr，> 95％ee）构造一系列四氢异喹啉衍生物。此外，事先通过使用量子电子圆二色性计算和ECD光谱法确定了产物的绝对构型。
• Synthesis and characterization of a diaziridinium ion. Conversion of 3,4-dihydroisoquinolines to 4,5-dihydro-3H-benzo[2,3]diazepines via a formal N-insertion process
  作者：Julia M. Allen、Tristan H. Lambert

  DOI：10.1016/j.tet.2014.03.015

  日期：2014.7