2,3-dihydro-2,4-diphenyl-1H-benzo[b][1,5]diazepine | 40358-30-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 2,3-dihydro-2,4-diphenyl-1H-benzo[b][1,5]diazepine
• 英文别名: 2,4-diphenyl-2,3-dihydrodibenzo<1,4>diazepine；2,4-diphenyl-2,3-dihydro-1H-benzo[b][1,4]diazepine；2,3-dihydro-2,4-diphenyl-1H-1,5-benzodiazepine；2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepine；2,4-diphenyl-1H,2H,3H-benzo[b]1,4-diazepine；2,4-diphenyl-2,3-dihydrobenzodiazepine
• CAS: 40358-30-3
• 化学式: C₂₁H₁₈N₂
• 分子量: 298.387
• InChiKey: KLUUDQZFQBRKNI-UHFFFAOYSA-N

物化性质

• 熔点：
  129-130 °C
• 沸点：
  471.9±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-2,4-diphenyl-1H-benzo[b][1,5]diazepine 在 乙酸酐 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以71%的产率得到苯亚甲基苯乙酮
  参考文献：
  名称：

  Chemical transformations of 2,4-diaryl-2,3-dihydro-1H,1,5-benzodiazepines

  摘要：

  DOI：

  10.1007/bf00506159
• 作为产物：
  描述：

  2-硝基苯胺 、 苯亚甲基苯乙酮 在 三氢化钐 、 四氯化钛 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到2,3-dihydro-2,4-diphenyl-1H-benzo[b][1,5]diazepine
  参考文献：
  名称：

  DERIVATIVES OF 2,3-DIHYDRO-1H-1,5-BENZODIAZEPINE FROMo-NITROANILINES AND CHALCONES INDUCED BY LOW-VALENT TITANIUM

  摘要：

  2,3-Dihydro-1H-1,5-benzodiazepines have been prepared in good yield by reaction of o-nitroanilines with chalcones induced by the TiCl4-Sm-THF system under mild reaction conditions.

  DOI：

  10.1081/scc-120001997

文献信息

• Construction of the 1,5-Benzodiazepine Skeleton from <i>o</i>-Phenylendiamine and Propargylic Alcohols via a Domino Gold-Catalyzed Hydroamination/Cyclization Process
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Antonia Iazzetti

  DOI：10.1021/acs.orglett.6b01720

  日期：2016.8.5

  The gold-catalyzed reaction of o-phenylendiamine with propargylic alcohols affords 1,5-benzodiazepines bearing different substituents on the 2 and 4 positions. The method allows even for the selective preparation of 4-substituted 1,5-benzodiazepine derivatives.

  邻苯二胺与炔丙醇的金催化反应，得到在2和4位带有不同取代基的1,5-苯并二氮杂pine。该方法甚至允许选择性地制备4-取代的1，5-苯并二氮杂卓衍生物。
• Dynamic Kinetic Resolution Approach for the Asymmetric Synthesis of Tetrahydrobenzodiazepines Using Transfer Hydrogenation by Chiral Phosphoric Acid
  作者：Kosaku Horiguchi、Eri Yamamoto、Kodai Saito、Masahiro Yamanaka、Takahiko Akiyama

  DOI：10.1002/chem.201601611

  日期：2016.6.6

  Asymmetric synthesis of tetrahydrobenzodiazepines was achieved by transfer hydrogenation of dihydrobenzodiazepines with benzothiazoline having a hydrogen‐bonding donor substituent by means of a newly synthesized chiral phosphoric acid. This method was applicable to various racemic dihydrobenzodiazepines to give the corresponding products in good yields with excellent diastereoselectivities and enantioselectivities

  四氢苯并二氮杂卓的不对称合成是通过新合成的手性磷酸与具有氢键供体取代基的苯并噻唑啉转移氢化而实现的。该方法适用于各种外消旋二氢苯并二氮杂卓，利用动态动力学拆分，以良好的非对映选择性和对映选择性，以良好的收率得到相应的产物。此外，理论研究充分阐明了在3,3'-位的大取代基对催化剂和苯并噻唑啉上的氢键供体取代基的影响。
• Graphite oxide: a metal free highly efficient carbocatalyst for the synthesis of 1,5-benzodiazepines under room temperature and solvent free heating conditions
  作者：Ramen Jamatia、Ajay Gupta、Binoyargha Dam、Mithu Saha、Amarta Kumar Pal

  DOI：10.1039/c6gc03110b

  日期：——

  We report a sustainable and metal free carbocatalyst, graphite oxide, for the synthesis of 1,5-benzodiazepines under room temperature and solvent free heating conditions.

  我们报告了一种在室温和无溶剂加热条件下合成1,5-苯并二氮杂pine的可持续且无金属的碳催化剂，氧化石墨。
• [BPy]HSO₄Acidic Ionic Liquid as a Novel, Efficient, and Environmentally Benign Catalyst for Synthesis of 1,5‐Benzodiazepines under Mild Conditions
  作者：Yuying Du、Fuli Tian、Wenzhi Zhao

  DOI：10.1080/00397910600616602

  日期：2006.7

  Abstract A novel and simple ionic liquid methodology for the synthesis of 1,5‐benzodiazepines is described. 1‐Butylpyridinium hydrogen sulphate ([BPy]HSO4), an acidic room‐temperature ionic liquid, as a novel and efficient catalyst, was synthesized and used in the preparation of a series of 1,5‐benzodiazepine derivatives by the reaction of o‐phenylenediamine with chalcones under mild conditions. This

  摘要描述了一种用于合成 1,5-苯二氮卓类药物的新颖且简单的离子液体方法。1-丁基吡啶鎓硫酸氢盐 ([BPy]HSO4) 是一种酸性室温离子液体，作为一种新型高效催化剂，被合成并用于通过 o- 反应制备一系列 1,5-苯二氮卓衍生物。苯二胺与查耳酮在温和条件下。该方法简单、高效、环保、经济、不含有毒催化剂，并且对1,5-苯二氮卓类的形成具有良好的收率
• Solvent‐Free Synthesis of 1,5‐Benzothiazepines and Benzodiazepines on Inorganic Supports
  作者：Mitsuo Kodomari、Tomohiro Noguchi、Tadashi Aoyama

  DOI：10.1081/scc-120034159

  日期：2004.12.31

  Abstract 1,5‐Benzothiazepines and 1,5‐benzodiazepines have been synthesized in solvent‐free conditions from chalcones and o‐aminothiophenol or o‐phenylenediamine in the presence of inorganic support. Silica gel was found to be an effective support for the synthesis of 1,5‐benzothiazepines, whereas alumina was effective for the synthesis of 1,5‐benzodiazepines.

  摘要 1,5-苯并二氮杂和 1,5-苯二氮卓类化合物在无溶剂条件下由查耳酮和邻氨基苯硫酚或邻苯二胺在无机载体存在下合成。发现硅胶是合成 1,5-苯并噻嗪类药物的有效载体，而氧化铝对合成 1,5-苯二氮卓类药物有效。