methyl 2-allyl-4-nitrobenzoate | 193806-52-9

• 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: methyl 2-allyl-4-nitrobenzoate
• 英文别名: Methyl 4-nitro-2-prop-2-enylbenzoate
• CAS: 193806-52-9
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: VTKOZIFWMVMCIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  348.4±37.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-allyl-4-nitrobenzoate 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 tetrafluoroboric acid 、 草酰氯 、 N,N-二甲基甲酰胺 、 sodium iodide 、 亚硝酸异戊酯 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 7.0h， 生成 1-羟基-6-硝基萘
  参考文献：
  名称：

  Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions

  摘要：

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.

  DOI：

  10.1021/jo970500j
• 作为产物：
  描述：

  2-溴-4-硝基苯甲酸甲酯 、 烯丙基三丁基锡 在 tris(dibenzylideneacetone)dipalladium (0) 三苯基膦 作用下， 以91%的产率得到methyl 2-allyl-4-nitrobenzoate
  参考文献：
  名称：

  Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions

  摘要：

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.

  DOI：

  10.1021/jo970500j

文献信息

• CONDENSED HETEROCYCLIC COMPOUND
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US20170349605A1

  公开（公告）日：2017-12-07

  The present invention relates to a condensed heterocyclic compound that has an enteropeptidase inhibitory effect and is useful in the treatment or prevention of obesity, diabetes mellitus, or the like, and a medicament containing the same. Specifically, the present invention relates to a compound represented by the following formula (I) or a salt thereof, and a medicament containing the same [in the formula, each symbol is as defined in the specification].

  本发明涉及一种具有肠肽酶抑制作用的缩合杂环化合物，可用于治疗或预防肥胖、糖尿病等疾病，以及含有该化合物的药物。具体而言，本发明涉及以下式（I）所代表的化合物或其盐，以及含有该化合物的药物[在式中，每个符号如规范中定义]。
• Discovery of a novel series of medium-sized cyclic enteropeptidase inhibitors
  作者：Fumiaki Kikuchi、Zenichi Ikeda、Keiko Kakegawa、Youichi Nishikawa、Shigekazu Sasaki、Koichiro Fukuda、Kazuaki Takami、Yoshihiro Banno、Hitoaki Nishikawa、Naohiro Taya、Takashi Nakahata、Sachiko Itono、Hiroaki Yashiro、Kazue Tsuchimori、Hideyuki Hiyoshi、Masako Sasaki、Kimio Tohyama、Kouta Matsumiya、Youko Ishihara、Tetsuji Kawamoto、Masahiro Kamaura、Masanori Watanabe、Tomoyuki Kitazaki、Tsuyoshi Maekawa、Minoru Sasaki

  DOI：10.1016/j.bmc.2023.117462

  日期：2023.10

  study was to discover novel enteropeptidase inhibitors showing more potent in vivo efficacy while retaining low systemic exposure. Inhibitory mechanism-based drug design led us to cyclize ester 2 to medium-sized lactones, showing potent enteropeptidase inhibitory activity and improving the ester stability, thus increasing fecal protein output in vivo. Optimization on the linker between two benzene rings

  肠肽酶位于十二指肠，参与肠道蛋白质消化。我们已经报道了全身暴露量较低的肠肽酶抑制剂。本研究的目的是发现新型肠肽酶抑制剂，其在体内表现出更有效的功效，同时保持较低的全身暴露量。基于抑制机制的药物设计使我们将酯2环化为中等大小的内酯，显示出有效的肠肽酶抑制活性并提高了酯的稳定性，从而增加了体内粪便蛋白的输出。对两个苯环之间的连接体进行优化，发现了醚内酯6b，其表现出进一步增强的肠肽酶抑制活性和较长的抑制状态持续时间。与铅2相比，小鼠口服6b显着提高了粪便蛋白产量。此外，6b显示出较低的全身暴露以及较低的肠道吸收。此外，我们还确定了用于放大合成6b的 10 元内酯化方法，该方法不需要高稀释条件。
• Synthesis and structure–activity studies of the V-ATPase inhibitor saliphenylhalamide (SaliPhe) and simplified analogs
  作者：Jose Garcia-Rodriguez、Saurabh Mendiratta、Michael A. White、Xiao-Song Xie、Jef K. De Brabander

  DOI：10.1016/j.bmcl.2015.09.021

  日期：2015.10

  An efficient total synthesis of the potent V-ATPase inhibitor saliphenylhalamide (SaliPhe), a synthetic variant of the natural product salicylihalamide A (SaliA), has been accomplished aimed at facilitating the development of SaliPhe as an anticancer and antiviral agent. This new approach enabled facile access to derivatives for structure-activity relationship studies, leading to simplified analogs that maintain SaliPhe's biological properties. These studies will provide a solid foundation for the continued evaluation of SaliPhe and analogs as potential anticancer and antiviral agents. (C) 2015 Elsevier Ltd. All rights reserved.
• US9975903B2
  申请人：——

  公开号：US9975903B2

  公开（公告）日：2018-05-22
• Generation and Cyclization of Acyl Radicals from Thiol Esters Under Nonreducing, Tin-Free Conditions
  作者：David Crich、Xiaolin Hao

  DOI：10.1021/jo970500j

  日期：1997.8.1

  The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-amino-phenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is removed and the amine reacted with isoamyl nitrite to give a series of diazonium salts. Exposure to iodide in acetone solution then generates the aryl radical, which undergoes intramolecular homolytic substitution at sulfur with liberation of the acylradical. Following acyl radical cyclization, quenching by iodine and then elimination of HI leads to the isolation of alpha-methylene cycloalkanones in good yield.