1-benzyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dione | 5973-20-6

• 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: 1-benzyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dione
• 英文别名: 1-benzyl-3H-1(H),4(H)-benzodiazepin-2,5-dione；1-benzyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione；1-benzyl-3H-1,4-benzodiazepine-2,5(1H,4H)-dione；1-Benzyl-3H-1.4-benzodiazepin-2.5(1H,4H)-dion；1-Benzyl-3,4-dihydro-1,4-benzodiazepine-2,5-dione
• CAS: 5973-20-6
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: BZJHEQQAJDSYGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 1-benzyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 邻二甲苯 为溶剂， 反应 0.33h， 以79%的产率得到5-benzyl-2-propyl-4H,5H-[1,3]oxazolo[4,5-c]quinolin-4-one
  参考文献：
  名称：

  Scaffold Hopping via a Transannular Rearrangement–Encompassing Cascade

  摘要：

  A novel reaction cascade for converting benzodiazepinediones into oxazoloquinolinones using carboxylic acid anhydrides in the presence of base has been developed using flow methods. Products are obtained in yields up to 98%.

  DOI：

  10.1021/ol4000444
• 作为产物：
  描述：

  靛红酸酐 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 121.0h， 生成 1-benzyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dione
  参考文献：
  名称：

  Scaffold Hopping via a Transannular Rearrangement–Encompassing Cascade

  摘要：

  A novel reaction cascade for converting benzodiazepinediones into oxazoloquinolinones using carboxylic acid anhydrides in the presence of base has been developed using flow methods. Products are obtained in yields up to 98%.

  DOI：

  10.1021/ol4000444

文献信息

• A Novel Solid-Phase Synthetic Method for 1,4-Benzodiazepine-2,5-dione Derivatives
  作者：Moon-Kook Jeon、Jeong-Jin Kwon、Myung-Su Kim、Young-Dae Gong

  DOI：10.1055/s-2008-1078484

  日期：——

  Utilizing polymer-bound anthranilic acid derivatives 1, we were able to obtain the 1,4-benzodiazepine-2,5-dione derivatives 3 (R3 = H, R4 = H, MeO, Cl) through an unprecedented reaction sequence, reductive alkylation-N-protected amino acid coupling-deprotective cyclization, in 28-71% five-step overall isolated yields and 95-99% purities from Wang resin 4. Applying the novel protocol to the resin 2, the 7-benzamido-1,4-benzodiazepine-2,5-dione derivatives 3 (R1 = Bn, R4 = 7-BzNH) could be obtained in 19-42% seven- or eight-step overall isolated yields and 92-98% purities from AMEBA resin 7.

  利用与聚合物结合的蒽酸衍生物 1，我们通过前所未有的反应序列，即还原烷基化-N-保护性氨基酸偶联-保护性环化反应，得到了 1,4-苯并二氮杂卓-2,5-二酮衍生物 3（R3 = H，R4 = H，MeO，Cl），五步法的总分离产率为 28-71%，纯度为 95-99%。对树脂 2 采用新方案，可获得 7-苯甲酰胺基-1,4-苯并二氮杂卓-2,5-二酮衍生物 3（R1 = Bn，R4 = 7-BzNH），其在 AMEBA 树脂 7 中的七步或八步分离收率为 19-42%，纯度为 92-98%。
• Mohiuddin, G.; Reddy, P. S. N.; Ahmed, Khalil, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 905 - 907
  作者：Mohiuddin, G.、Reddy, P. S. N.、Ahmed, Khalil、Ratnam, C. V.

  DOI：——

  日期：——
• MOHIUDDIN G.; REDDY P. S. N.; AHMED K. HALIL; RATNAM C. V., INDIAN J. CHEM., 24,(1985) N 9, 905-907
  作者：MOHIUDDIN G.、 REDDY P. S. N.、 AHMED K. HALIL、 RATNAM C. V.

  DOI：——

  日期：——
• Scaffold Hopping <i>via</i> a Transannular Rearrangement–Encompassing Cascade
  作者：Johannes L. Vrijdag、An M. Van den Bogaert、Wim M. De Borggraeve

  DOI：10.1021/ol4000444

  日期：2013.3.1

  A novel reaction cascade for converting benzodiazepinediones into oxazoloquinolinones using carboxylic acid anhydrides in the presence of base has been developed using flow methods. Products are obtained in yields up to 98%.