3-methyl-4,5-dihydro-1H-benzo[e][1,4]diazepin-2(3H)-one | 258850-07-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-methyl-4,5-dihydro-1H-benzo[e][1,4]diazepin-2(3H)-one
• 英文别名: 3-Methyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one
• CAS: 258850-07-6
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: SBBGNRXYCGCZGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-溴-3-甲基-2-丁烯 、 3-methyl-4,5-dihydro-1H-benzo[e][1,4]diazepin-2(3H)-one 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以41%的产率得到3-methyl-4-(3-methyl-2-butenyl)-3,4-dihydro-1H,5H-1,4-benzodiazepin-2-one
  参考文献：
  名称：

  Synthesis and anti-HIV activity of 1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one (TBO) derivatives. truncated 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (TIBO) analogues

  摘要：

  4,5,6,7-Tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (TIBO), 1, have been shown to significantly inhibit HIV-1 replication, as reported in detail in our prior publications. Since our earlier reports, we have modified the TIBO structures 1 by removing the 5-membered ring of 1, generating 1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-ones (TBO), 4, a bicyclic series of compounds. Although compounds 4 possess modest activity when compared to TIBO analogues 1, they clearly demonstrated significant anti-HIV-1 activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00198-4
• 作为产物：
  描述：

  (+/-)-ethyl N-[(2-aminophenyl)methyl]alanine 在 1-羟基苯并三唑 作用下， 以 甲苯 为溶剂， 以7%的产率得到3-methyl-4,5-dihydro-1H-benzo[e][1,4]diazepin-2(3H)-one
  参考文献：
  名称：

  Synthesis and anti-HIV activity of 1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one (TBO) derivatives. truncated 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (TIBO) analogues

  摘要：

  4,5,6,7-Tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (TIBO), 1, have been shown to significantly inhibit HIV-1 replication, as reported in detail in our prior publications. Since our earlier reports, we have modified the TIBO structures 1 by removing the 5-membered ring of 1, generating 1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-ones (TBO), 4, a bicyclic series of compounds. Although compounds 4 possess modest activity when compared to TIBO analogues 1, they clearly demonstrated significant anti-HIV-1 activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00198-4

文献信息

• Synthesis of Chiral 3-Substituted 1,3,4,5-Tetrahydro-1,4-benzo- diazepin-2-ones<i>via</i>a Domino Copper-Catalyzed S_N2/Coupling Reaction
  作者：Dongming Lu、Chang Ma、Shuai Yuan、Lihong Zhou、Qingle Zeng

  DOI：10.1002/adsc.201500477

  日期：2015.11.16

  A novel protocol for the facile synthesis of chiral 3-substituted 1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-ones via a domino reaction has been developed, which involves a cascade of SN2 nucleophilic substitution and copper-catalyzed CN coupling reactions of α-amino acid amides and ortho-halobenzyl halides. This protocol has some merits, such as one-pot process, easy operation, a wide scope of substrates

  已开发了一种通过多米诺反应容易地合成手性3-取代的1,3,4,5-四氢苯并[ e ] [1,4]二氮杂-2-酮的新方法，该方法涉及级联的S N 2 α-氨基酸酰胺与邻卤代苄基卤化物的亲核取代和铜催化的CN偶联反应 该协议具有一些优点，例如一锅法，易于操作，基板范围广。此外，在反应过程中没有发生严重的外消旋作用。
• Synthesis and anti-HIV activity of 1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-one (TBO) derivatives. truncated 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (TIBO) analogues
  作者：Henry J. Breslin、Michael J. Kukla、Teresa Kromis、Heather Cullis、Fons De Knaep、Rudi Pauwels、Koen Andries、Erik De Clercq、Marcel A.C. Janssen、Paul A.J. Janssen

  DOI：10.1016/s0968-0896(99)00198-4

  日期：1999.11

  4,5,6,7-Tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-ones (TIBO), 1, have been shown to significantly inhibit HIV-1 replication, as reported in detail in our prior publications. Since our earlier reports, we have modified the TIBO structures 1 by removing the 5-membered ring of 1, generating 1,3,4,5-tetrahydro-2H-1,4-benzodiazepin-2-ones (TBO), 4, a bicyclic series of compounds. Although compounds 4 possess modest activity when compared to TIBO analogues 1, they clearly demonstrated significant anti-HIV-1 activity. (C) 1999 Elsevier Science Ltd. All rights reserved.