4-Hydroxy-5-methoxy-2-nitrobenzoyl chloride | 182277-06-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Hydroxy-5-methoxy-2-nitrobenzoyl chloride
• CAS: 182277-06-1
• 化学式: C₈H₆ClNO₅
• 分子量: 231.592
• InChiKey: ZQXMEYWYAVGBEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-5-methoxy-2-nitrobenzoyl chloride 在 sodium azide 、 二异丁基氢化铝 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 (2S)-1-(2-azido-4-hydroxy-5-methoxybenzoyl)pyrrolidine-2-carbaldehyde
  参考文献：
  名称：

  HMDST叠氮基还原环化法合成吡咯并[2,1- c ] [1,4]苯并二氮杂s

  摘要：

  吡咯并[2,1- c ] [1,4]苯并二氮杂（PBD）环系统的一种新的简便的合成已通过使用六甲基二硅噻吩（HMDST）对叠氮化物进行还原环化而实现。母体未取代的PBD和天然产物DC-81也已经以良好的总产率制备。

  DOI：

  10.1016/s0040-4039(96)01484-0
• 作为产物：
  描述：

  2-硝基-4-苄氧基-5-甲氧基苯甲酸 在 草酰氯 、 三氟化硼乙醚 、 乙硫醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 4-Hydroxy-5-methoxy-2-nitrobenzoyl chloride
  参考文献：
  名称：

  吡咯并[2,1-c] [1,4]苯并二氮杂s的新方法：DC-81的合成，DNA结合和细胞毒性

  摘要：

  描述了两种天然结合DNA的抗肿瘤抗生素DC-81的途径，其中一种涉及基于酸性树脂的新型环化过程。第二种途径涉及新化合物6-硝基香草酸的合成，6-硝基香草酸是许多天然存在的PBD的关键A环成分。这些途径提供了足够量的DC-81，可以在DNA结合和体外细胞毒性研究中进行完整的表征和评估。

  DOI：

  10.1016/s0040-4020(01)88134-5

文献信息

• A new facile procedure for the preparation of pyrrolo[2,1-c][1,4]benzodiazepines: Synthesis of the antibiotic DC-81 and its thio analogue
  作者：Ahmed Kamal、B.S.Praveen Reddy、B.S.Narayan Reddy

  DOI：10.1016/0040-4039(96)00243-2

  日期：1996.3

  An efficient synthesis of the imine form of the pyrrolo[2,1-c][1,4]benzodiazepine ring system based on a new reductive cyclization procedure is described. The naturally occuring antibiotic DC-81(5c) and its 5-thio analogue (7c) have also been synthesized to illustrate the usefulness of this methodology.

  描述了一种基于新的还原环化程序的吡咯并[2,1- c ] [1,4]苯并二氮杂ring环系统的亚胺形式的有效合成。还合成了天然存在的抗生素DC-81（5c）及其5-硫代类似物（7c），以说明该方法的有用性。
• Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics: Oxidation of cyclic secondary amine with TPAP
  作者：Ahmed Kamal、Philip W Howard、B.S Narayan Reddy、B.S Praveen Reddy、David E Thurston

  DOI：10.1016/s0040-4020(97)00033-1

  日期：1997.3

  A facile procedure for the preparation of the imine form of the pyrrolo[2,1-c][1,4]-benzodiazepine ring system by the oxidation of cyclic secondary amine with catalytic amounts of tetra-n-propylammonium perruthenate (TPAP) and N-methylmorpholine N-oxide (NMO) as a co-oxidant is described. This oxidative method is devoid of side-products and is thus a significant improvement over the Swern oxidation

  通过催化量的四正丙基过钌酸铵（TPAP）氧化环仲胺氧化吡咯并[2,1- c ] [1,4]-苯并二氮杂ring环系统的亚胺形式的简便方法描述了作为辅助氧化剂的N-甲基吗啉N-氧化物（NMO）。这种氧化方法没有副产物，因此比以前报道的Swern氧化有很大的改进。
• A new route for the synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via oxidation of cyclic secondary amine
  作者：Ahmed Kamal、N. Venugopal Rao

  DOI：10.1039/cc9960000385

  日期：——

  The synthesis of the imine-containing pyrrolo[2,1-c][1,4]benzodiazepine DNA–binding antitumour antibiotics was achieved by a new method of oxidation of cyclic secondary amines which does not endanger the stereochemical integrity of the C-11a position.

  合成含亚胺的吡咯并[2,1-c][1,4]苯并二氮杂烯DNA结合抗肿瘤抗生素采用了一种新的氧化环状二级胺的方法，这种方法不会危害C-11a位点的立体化学完整性。
• An efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via reductive cyclization
  作者：Ahmed Kamal、B.S.Nararyan Reddy、B.S.Praveen Reddy

  DOI：10.1016/s0960-894x(97)00314-4

  日期：1997.7

  A new and convenient one-pot synthesis of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) ring system has been achieved by a reductive cyclization employing N,N-dimethylhydrazine and FeCl3.6H(2)O in good yields. (C) 1997 Elsevier Science Ltd.
• Asymmetric syntheses of piperidino-benzodiazepines through ‘cation-pool’ host/guest supramolecular approach and their DNA-binding studies
  作者：Nagula Markandeya、Nagula Shankaraiah、Ch. Sanjeeva Reddy、Leonardo Silva Santos、Ahmed Kamal

  DOI：10.1016/j.tetasy.2010.10.030

  日期：2010.11

  The asymmetric synthetic approach to piperidino-benzodiazepine 4a (a homolog of DC-81) has been developed The absolute stereochemistry of 4 and 5 has been assigned to be (S) at C-12a position This procedure features the use of a canon-pool strategy and also a host/guest supramolecular co-catalysis approach In this study the chloroformate of 8-phenylmenthyl has been employed as a chiral auxiliary and includes one-pot conditions for anodic oxidation which are followed by nucleophilic addition to an N-acyliminium ion In addition intramolecular azido reductive-cyclization and nitro reductive dithioacetal deprotective tandem-cyclization approaches have also been utilized for the syntheses of these compounds 4a b and 5a b Some of the representative compounds exhibited an enhanced DNA-binding ability in comparison to the natural product DC-81 (C) 2010 Elsevier Ltd All rights reserved