2,3-dihydro-2-(3',4'-methylenedioxyphenyl)-4-phenyl-1H-1,5-benzodiazepine

• 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-(3',4'-methylenedioxyphenyl)-4-phenyl-1H-1,5-benzodiazepine
• 英文别名: 2-(1,3-benzodioxol-5-yl)-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepine
• 化学式: C₂₂H₁₈N₂O₂
• 分子量: 342.397
• InChiKey: OHHPGAKPSTXBOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙酮 在 Bi(NO₃)3 on neutral alumina 作用下， 反应 5.38h， 生成 2,3-dihydro-2-(3',4'-methylenedioxyphenyl)-4-phenyl-1H-1,5-benzodiazepine
  参考文献：
  名称：

  A new and efficient one-pot solid-supported synthesis of 1,2,4,6-tetraaryl-1,4-dihydropyridines

  摘要：

  在 Bi(III)nitrate-Al2O3 表面通过查耳酮和取代苯胺的一锅反应获得了 1,2,4,6-四芳基-1,4-二氢吡啶。该反应似乎是通过 Bi(III) 烯化查耳酮的β-氧合反应进行的，然后是迈克尔加成和杂环反应，并同时进行逆醛醇歧化反应。苯胺的正对位和对位存在活环基团似乎对反应至关重要：1,2,4,6-四卤代-1,4-二氢吡啶，查耳酮，取代苯胺，硝酸铋（III）-氧化铝催化剂。

  DOI：

  10.1139/v06-128

文献信息

• DERIVATIVES OF 2,3-DIHYDRO-1H-1,5-BENZODIAZEPINE FROM<i>o</i>-NITROANILINES AND CHALCONES INDUCED BY LOW-VALENT TITANIUM
  作者：Yongmin Ma、Yongmin Zhang

  DOI：10.1081/scc-120001997

  日期：2002.1

  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.
• Solvent-Free Synthesis of Some 1,5-Benzothiazepines and Benzodiazepines and Their Antibacterial Activity
  作者：R. K. Saini、Y. C. Joshi、P. Joshi

  DOI：10.1080/10426500701852661

  日期：2008.8.4

  An efficient and convenient synthesis of 1, 5-benzothiazepines (3a-3f) and 1, 5-benzodiazepines (4a-4f) from chalcones (2a-2f) by the action of o-amino thiophenol and o-phenylenediamine in the presence of inorganic support is reported. These compounds are characterized by elemental analysis and spectral studies viz: IR, (1)H NMR, and (13)C NMR. Newly synthesized compounds were screened for their antibacterial activity against -subtilis, E-coli, and S. typhis.
• A new and efficient one-pot solid-supported synthesis of 1,2,4,6-tetraaryl-1,4-dihydropyridines
  作者：Anil K Verma、Summon Koul、Tej K Razdan、Kamal K Kapoor

  DOI：10.1139/v06-128

  日期：2006.8.1

  1,2,4,6-Tetraaryl-1,4-dihydropyridines were obtained by the one-pot reaction of chalcones and substituted anilines on the surface of Bi(III)nitrate-Al₂O₃. The reaction seems to proceed via β-oxygenation of Bi(III) enolised chalcones followed by Michael addition and heteroannulation with simultaneous retro aldol disproportionation. The presence of the ring-activating groups at ortho and para positions in the aniline seems to be essential for the reaction.Key words: 1,2,4,6-tetraryl-1,4-dihydropyridines, chalcones, substituted anilines, Bi(III) nitrate-alumina catalyst.

  在 Bi(III)nitrate-Al2O3 表面通过查耳酮和取代苯胺的一锅反应获得了 1,2,4,6-四芳基-1,4-二氢吡啶。该反应似乎是通过 Bi(III) 烯化查耳酮的β-氧合反应进行的，然后是迈克尔加成和杂环反应，并同时进行逆醛醇歧化反应。苯胺的正对位和对位存在活环基团似乎对反应至关重要：1,2,4,6-四卤代-1,4-二氢吡啶，查耳酮，取代苯胺，硝酸铋（III）-氧化铝催化剂。