ethyl 2-(2-ethoxy-2-oxoethyl)-7-methyl-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate | 1224441-71-7

• 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: ethyl 2-(2-ethoxy-2-oxoethyl)-7-methyl-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
• 英文别名: ethyl 2-(2-ethoxy-2-oxoethyl)-7-methyl-2,5-dihydro-1H-1,5-benzodiazepine-3-carboxylate
• CAS: 1224441-71-7
• 化学式: C₁₇H₂₂N₂O₄
• 分子量: 318.373
• InChiKey: OOVZHJIDHMERPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-二氨基甲苯 、 丙炔酸乙酯 在 tert-butylammonium hexafluorophosphate(V) 、 calcium(II) trifluoromethanesulfonate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 生成 (E)-ethyl-2-(2-ethoxy-2-oxoethyl)-8-methyl-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate 、 ethyl 2-(2-ethoxy-2-oxoethyl)-7-methyl-2,5-dihydro-1H-benzo[b][1,4]diazepine-3-carboxylate
  参考文献：
  名称：

  β-烯胺酸酯的区域选择性分子内环化：含氮特权分子的多样性导向合成。

  摘要：

  在无溶剂的钙催化下描述了多样性导向的区域选择性β-烯氨基酯的分子内环化反应。对2-氨基芳基酮和丙酸烷基酯进行[4 + 2]环化，生成取代的喹啉；与过量的丙酸烷基酯一起，通过[4 + 2 + 1]环化形成苯并二氮杂。我们还描述了通过[4 + 2 + 2]环化法一锅，三组分合成喹啉衍生物。有趣的是，2-氨基芳基酮会发生自缩合[4 + 4]，生成二苯并重氮电影。

  DOI：

  10.1016/j.tetlet.2018.01.064

文献信息

• A Novel Strategy for the Construction of Functionalized 1,5- Benzodiazepines<i>via</i>a Tandem Conjugated Addition/Cyclization Process
  作者：Jian Li、Shaoyu Li、Chunju Li、Yuejin Liu、Xueshun Jia

  DOI：10.1002/adsc.200900736

  日期：2010.2.15

  A novel approach for the synthesis of functionalized 1,5-benzodiazepine is described. The protocol is triggered by a tandem conjugated addition/cyclization process from the readily available starting materials 1,2-phenylenediamine and ethyl propiolate. The products have secondary amino and ester groups, and a β-enamino ester, which can serve in further functionalizations to produce molecular diversity

  描述了一种合成官能化的1，5-苯并二氮杂novel的新方法。该协议是由容易获得的起始原料1,2-苯二胺和丙酸乙酯通过串联共轭加成/环化过程触发的。该产物具有仲氨基和酯基，以及β-烯胺酯，其可以用于进一步的官能化以产生分子多样性。
• In(OTf)3-Catalyzed Synthesis of Functionalized 1,5-Benzodiazepines from o-Phenylenediamine and Alkyl Propiolates under Solvent-Free Reaction Conditions
  作者：Haisheng Wu、Jin Yang、Lei Wang

  DOI：10.1002/cjoc.201180307

  日期：2011.8

  environmental‐friendly, and practical method for the synthesis of benzodiazepine derivatives through a reaction of substituted o‐phenylenediamines with alkyl propiolates has been developed. The reactions generated the 1,5‐benzodiazepines in good to excellent yields in the presence of catalytic amount of In(OTf)3 under solvent‐free reaction conditions.

  通过取代的邻苯二胺与丙酸烷基酯的反应合成苯二氮卓衍生物的一种简单，环保，实用的方法已经开发出来。在无溶剂反应条件下，在催化量的In（OTf）3存在下，反应以良好的产率产生了1,5-苯并二氮杂卓。
• Synthesis and inhibition studies towards the discovery of benzodiazepines as potential antimalarial compounds
  作者：Drista Sharma、Abhishek Pareek、Hemant Arya、Rani Soni、Praveen Rai、Akhil Agrawal、Surendra Nimesh、Diwakar Kumar、Srinivasarao Yaragorla、Tarun Kumar Bhatt

  DOI：10.1016/j.exppara.2022.108411

  日期：2022.12

  apicoplast in the survival of the parasite. In this study, we present the rational design strategy employing sustainable catalysis for the synthesis of benzodiazepine (BDZ) conformers followed by their biological evaluation as prospective inhibitors against the potential target of the IPP pathway, 1-deoxy-D-xylulose-5-phosphatereductoisomerase (DXR). The study reported the inhibitory profile of 8c and 6d

  基于靶标的针对顶端质体（一种非常重要的细胞器）的治疗方法的发现是一个压倒一切的观点。MEP 通路是一种经认可的药物靶标，可深入了解顶端体在寄生虫生存中的重要性。在这项研究中，我们提出了采用可持续催化合成苯并二氮卓 (BDZ) 构象异构体的合理设计策略，然后将其作为针对 IPP 途径潜在靶标 1-脱氧-D-木酮糖-5-磷酸还原异构酶的前瞻性抑制剂进行生物学评估(DXR)。该研究报告了 8c 和 6d 对寄生虫发育红细胞阶段唯一药物靶标的典型步骤的抑制作用。
• Gallium(III) triflate-catalyzed [4+2+1] cycloadditions for the synthesis of novel 3,4-disubstituted-1,5-benzodiazepines
  作者：Yao-Jia Jiang、Jing-Jing Cai、Jian-Ping Zou、Wei Zhang

  DOI：10.1016/j.tetlet.2009.11.049

  日期：2010.1

  Gallium(III) triflate-catalyzed [4+2+1] cycloaddition of o-phenylenediamines and 2 equiv of alkynoate under solvent-free and ultrasonic irradiation conditions afforded novel 3,4-disubstituted-1,5-benzodiazepines in 82-90% yields. (C) 2009 Elsevier Ltd. All rights reserved.
• Regioselective intramolecular annulations of ambident β-enamino esters: A diversity-oriented synthesis of nitrogen-containing privileged molecules
  作者：Srinivasarao Yaragorla、Abhishek Pareek

  DOI：10.1016/j.tetlet.2018.01.064

  日期：2018.3

  intramolecular annulation of β-enamino esters is described under solvent-free, calcium-catalysis. 2-aminoaryl ketones and alkyl propiolates undergone a [4+2] annulation to yield substituted quinolines; with an excess of alkyl propiolates, benzodiazepines were formed via a [4+2+1] annulation. We also described a one-pot, 3-component synthesis of quinoline derivatives via a [4+2+2] annulation. Interestingly

  在无溶剂的钙催化下描述了多样性导向的区域选择性β-烯氨基酯的分子内环化反应。对2-氨基芳基酮和丙酸烷基酯进行[4 + 2]环化，生成取代的喹啉；与过量的丙酸烷基酯一起，通过[4 + 2 + 1]环化形成苯并二氮杂。我们还描述了通过[4 + 2 + 2]环化法一锅，三组分合成喹啉衍生物。有趣的是，2-氨基芳基酮会发生自缩合[4 + 4]，生成二苯并重氮电影。