3-甲基-3,4-二氢-1H-苯并[e][1,4]二氮杂烷-2,5-二酮 | 24919-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: 3-甲基-3,4-二氢-1H-苯并[e][1,4]二氮杂烷-2,5-二酮
• 英文名称: 3-methyl-3H-1(H),4(H)-benzodiazepin-2,5-dione
• 英文别名: 3H-3-methyl-1,4-benzodiazepin-(1H,4H)-2,5-dione；3-methyl-1,4-benzodiazepin-2,5-dione；3-Methyl-1.2.3.4-tetrahydro-5H-1,4-benzodiazepin；3-Methyl-2.5-dioxo-1.2.4.5-tetrahydro-3H-1.4-benzdiazepin；3-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione；3-Methyl-3H-1,4-benzodiazepin-2,5(1H,4H)-dion；3-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione
• CAS: 24919-37-7
• 化学式: C₁₀H₁₀N₂O₂
• mdl: MFCD02942360
• 分子量: 190.202
• InChiKey: LJONQULKOKMKBR-UHFFFAOYSA-N

物化性质

• 熔点：
  320.5-321 °C
• 沸点：
  510.2±39.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.21
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.2
• 氢给体数：
  2.0
• 氢受体数：
  2.0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-甲基-3,4-二氢-1H-苯并[e][1,4]二氮杂烷-2,5-二酮 在 四丁基溴化铵 、 potassium carbonate 、 三氟乙酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 3-methyl-1-[(2S,3R,4R)-2,3,4,5-tetrahydroxypentyl]-3,4-dihydro-1,4-benzodiazepine-2,5-dione
  参考文献：
  名称：

  Synthesis and amphiphilic properties of glycosyl-1,4-benzodiazepin-2,5-diones

  摘要：

  Glycosyl-l,4-benzodiazepin-2,5-diones were prepared by coupling polyhydroxylated groups at N-1 of the corresponding benzodiazepine. The groups include 1-deoxy-D,L-xylit-1-yl, 6-deoxy-D-glucopyranos-6-yl, and 6-deoxy-3-O-R-D-glucopyranos-6-yl (R = n-CnH2n+1 n = 8, 12, and 16). The structural variations of the sugar group allowed comparison of such amphiphilic data as water solubility (Sw), critical micelle concentration (CMC), and corresponding surface tension (gamma) values. At 25 degrees C, unsubstituted benzodiazepines have Sw values from 0.9 to 4.2 10(-3) mol L-1, whereas xylit-1-yl and 6-deoxy-D-glucopyranos-6-yl derivatives are, respectively, 7.4-25 and 58-204 times more soluble. Also, compounds with R = n-C8H17 are more soluble than corresponding benzodiazepines (1.4-5.8 times) and give micelles with CMC from 2.7 to 5.6 10-3 mol L-1 and corresponding gamma from 29 to 37 mN m(-1). In contrast, compounds with R = n-C12H25 and n-C16H33 are not soluble enough to reach the critical micelle concentration. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00163-4
• 作为产物：
  描述：

  在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-甲基-3,4-二氢-1H-苯并[e][1,4]二氮杂烷-2,5-二酮
  参考文献：
  名称：

  用 HCL 气体催化剂合成 1,4 苯二氮卓-2,5-二酮的新方法

  摘要：

  摘要 新合成了1,4-苯二氮卓酮4 ，特别是1,4-dihydro1H-1,4-benzodiazepine-2,5-dione, 4c关键中间体环戊二烯9 、环戊醇10 、环肽11和脱氢环肽12 。通过DMF中的干燥HCl气体对由邻氨基苯甲酸衍生物1和氨基酯2制备的化合物3的作用。

  DOI：

  10.1080/00397919308013783

文献信息

• Simple synthesis, structure and ab initio study of 1,4-benzodiazepine-2,5-diones
  作者：Khosrow Jadidi、Reza Aryan、Morteza Mehrdad、Thomas Lügger、F Ekkehardt Hahn、Seik Weng Ng

  DOI：10.1016/j.molstruc.2003.12.024

  日期：2004.4

  procedure for the synthesis of pyrido[2,1-c][1,4] benzodiazepine-6,12-dione ( 1 ) and 1,4-benzodiazepine-2,5-diones ( 2a – 2d ), using microwave irradiation and/or conventional heating is reported. The configuration of 1 was determined by single-crystal X-ray diffraction. A detailed ab initio B3LYP/6-31G* calculation of structural parameters and substituent effects on ring inversion barriers (Δ G # ) and

  摘要 合成吡啶并[2,1-c][1,4] benzodiazepine-6,12-dione ( 1 ) 和1,4-benzodiazepine-2,5-diones ( 2a – 2d ) 的简单程序，使用报告了微波辐射和/或常规加热。1的构型是通过单晶X射线衍射确定的。报告了详细的从头计算 B3LYP/6-31G* 的结构参数和取代基对环反转势垒 (Δ G # ) 的影响以及苯二氮卓类的自由能差异 (Δ G 0 )。
• Solid phase synthesis of 1,4-benzodiazepine-2,5-diones
  作者：John P. Mayer、Jingwen Zhang、Kirsten Bjergarde、Doug M. Lenz、John J. Gaudino

  DOI：10.1016/0040-4039(96)01845-x

  日期：1996.11

  1,4-benzodiazepine-2,5-diones were synthesized by a simple procedure utilizing polymer supported amino acids and o-nitrobenzoic acids or protected anthranilic acids. Cyclization of the common aminoamide intermediate with concomitant release from the support furnished the desired 1,4-benzodiazepine-2,5-diones. The products were recovered in high yields and exhibited excellent purities.

  通过简单的方法，利用聚合物负载的氨基酸和邻硝基苯甲酸或受保护的邻氨基苯甲酸合成1，4-苯并二氮杂-2，5-二酮。普通氨基酰胺中间体的环化，同时伴随着从载体上的释放，提供了所需的1，4-苯并二氮杂-2，5-二酮。以高收率回收产物，并显示出优异的纯度。
• A NOVEL ONE STEP APPROACH TO THE SYNTHESIS OF 3H-1,4-BENZODIAZEPIN-(1H,4H)-2,5-DIONES FROM 1,2,3-BENZOTRIAZIN-4-(3H)-ONE.
  作者：Renu Gupta、Reenu Sirohi、Sudha Shastri、D. Kishore

  DOI：10.1515/hc.2003.9.4.363

  日期：2003.1

  hydrolytic cleavage of N2-N3 bond to give rise to the transient formation of a diazonium compound which in appropriately substituted 3 is amenable further to products through the intra or intermolecular condensations. RESULTS AND DISCUSSION 1,2,3Benzotriazin-4-(3H)-ones (3) are most intensively studied class of 1,2,3-benzotriazine derivatives and effective method for their synthesis are known. The most

  l,2,3-苯并三嗪-4-(3H)-one(3)及其6-氯衍生物(4)与α-氨基酸热缩合产生3H-1,4-苯并二氮杂-(1H,4H)- 2,5-二酮(7-12) 的产率适中。环缩合被认为是通过形成亚胺烯酮中间体 (5) 进行的。引言 1,4-苯二氮卓类及其氧代衍生物代表了一类具有广泛精神药理学特性的活性化合物。我们寻求为 1,4 苯二氮卓合成开发新的一步策略，这使我们研究了具有经证实的合成潜力的材料在其合成中的应用。对文献的搜索表明，l,2,3-benzotriazin-4-(3H)-one (3) 具有非凡的能力，可以用酸、碱和在没有这些的情况下裂解其含氮环，在热条件下得到中间体苯并氮杂 5，该中间体已广泛用于合成。这促使我们研究其在 1,4-苯二氮卓合成中的应用。除了 Nesmeyanov 及其同事在 1973 年使用 30% 磷酸将 1 转化为 2（方案 1）的一次尝试之外，之前似乎没有其他尝试探索
• New routes to 1,4- benzodiazepin-2,5-diones
  作者：M. Akssira、M. Boumzebra、H. Kasmi、A. Dahdouh、M.-L. Roumestant、Ph. Viallefont

  DOI：10.1016/s0040-4020(01)85371-0

  日期：1994.1

  1,4-benzodiazepin-2,5-diones have been synthesized in good overall yields by two routes, the first one by cyclisation of dipeptides prepared from Boc anthranilic acid and alpha-amino acid methyl esters, the second one by reaction of N-carboxy alpha-amino acid anhydrides with Boc anthranilic acid.
• 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：——