methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylate | 41280-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylate
• 英文别名: methyl 3-chloro-5-methoxybenzo[b]thiophene-2-carboxylate；methyl 3-chloro-5-methoxybenzothiophene-2-carboxylate；3-chloro-5-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester；methyl 3-chloro-5-methoxy-benzo[b]thiophene-2-carboxylate
• CAS: 41280-81-3
• 化学式: C₁₁H₉ClO₃S
• 分子量: 256.71
• InChiKey: WWDSBGDUDDPVRU-UHFFFAOYSA-N

物化性质

• 熔点：
  116-117 °C(Solv: ethanol (64-17-5))
• 沸点：
  376.9±37.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-chloro-5-methoxy-1-benzothiophene-2-carboxylate 在 potassium nitrososulfonate 、 5%-palladium/activated carbon 、 氢气 、 硝酸 、 sodium acetate 、 溶剂黄146 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 丙酮 为溶剂， 反应 5.0h， 生成 methyl 4,7-dihydro-4,7-dioxo-5-methoxybenzothiophene-2-carboxylate
  参考文献：
  名称：

  Benzofuran-, benzothiophene-, indazole- and benzisoxazole-quinones: Excellent substrates for NAD(P)H:quinone oxidoreductase 1

  摘要：

  A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.071
• 作为产物：
  描述：

  3-(3-methoxyphenyl)propiolic acid 、 氯化亚砜 以18%的产率得到
  参考文献：
  名称：

  BONNIN C. M.; CADBY P. A; FREEMAN C. G.; WARD A. D., AUSTRAL. J. CHEM., 1979, 32, NO 4, 833-847

  摘要：

  DOI：

文献信息

• Axially Chiral 3,3'-Bi(1-benzothiophene)-2,2'-dicarboxylic Acid and Its Derivatives
  作者：Marie Mézlová、Hana Petříčková、Petr Maloň、Václav Kozmík、Jiří Svoboda

  DOI：10.1135/cccc20031020

  日期：——

  Ullmann dimerization of substituted methyl 3-X-1-benzothiophene-2-carboxylates 1-7 (X = Cl, Br) gave rise to the corresponding dimeric 3,3'-bi(1-benzothiophene) esters 8-13. Resolution of the title acid 20 by fractional crystallization of its mono- and bisquininium salt afforded pure (R)- and (S)-enantiomers, the optical purity and absolute configuration of which was confirmed by CD spectrometry and by X-ray crystallography. Ullmann dimerization of chiral oxazolines 23 and 24 derived from 2 proceeded without any diastereodifferentiation. Reduction of (R)- and (S)-20 afforded the corresponding (R)- and (S)-diols 29, which served as chiral ligands in a model enantioselective reduction of acetophenone. (R)- and (S)-1-phenylethan-1-ol were formed in 28 and 29% e.e., respectively.

  用替代基取代的甲基3-X-1-苯并噻吩-2-羧酸甲酯（X = Cl，Br）进行Ullmann二聚化反应，得到相应的二聯苯并噻吩酯（8-13）。通过对标题酸20进行单酰铵盐和双酰铵盐的分馏结晶，得到纯度较高的（R）-和（S）-对映体，其光学纯度和绝对构型通过CD光谱和X射线晶体学得到确认。从2衍生的手性噁唑啉23和24的Ullmann二聚化反应在没有差向异构化的情况下进行。对（R）-和（S）-20的还原得到相应的（R）-和（S）-二醇29，它们在模型对苯甲酮的对映选择性还原中作为手性配体。分别形成28%和29%的（R）-和（S）-1-苯基乙醇。
• Method for treating inflammatory disease in humans
  申请人：Warner-Lambert Company

  公开号：US05489586A1

  公开（公告）日：1996-02-06

  Benzothiophene, benzofuran and indole-thiazepinones, oxazepinones and diazepinones as well as methods of preparation thereof are described as agents which inhibit leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases.

  苯并噻吩、苯并呋喃和吲哚-噻吩酮、噁唑酮和二唑酮以及它们的制备方法被描述为抑制白细胞粘附到血管内皮的药物，并因此被认为是治疗炎症性疾病的有效治疗剂。
• [EN] USE OF THIAZEPINE, OXAZEPINE AND DIAZEPINE COUMPOUNDS FOR INHIBITING HIV, HERPESVIRUS AND SUPPRESSING THE IMMUNE SYSTEM<br/>[FR] EMPLOI DE COMPOSES DE THIAZEPINE, OXAZEPINE ET DIAZEPINE POUR INHIBER LE VIH, L'HERPESVIRUS ET DEPRIMER LE SYSTEME IMMUNITAIRE
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1996029077A1

  公开（公告）日：1996-09-26

  (EN) Benzothiophene, benzofuran and indole-thiazepinones, oxazepinones, and diazepinones are effective therapeutic agents for treating viral diseases, including those caused by herpesvirus and HIV.(FR) Le benzothiophène, le benzofurane et les indolethiazepinones, les oxazépinones et les diazépinones sont des agents thérapeutiques efficaces pour le traitement des maladies virales, y compris celles causées par les virus du herpèsvirus et le VIH.

  (中) 苯并噻吩、苯并呋喃和吲哚噻吩酮、噁唑酮和二氮杂环酮是有效的治疗剂，可用于治疗病毒性疾病，包括由疱疹病毒和HIV引起的疾病。
• [EN] BENZOTHIOPHENE, BENZOFURAN AND INDOLETHIAZEPINONES, OXAZEPINONES AND DIAZEPINONES AS INHIBITORS OF CELL ADHESION AND AS INHIBITORS OF HIV<br/>[FR] THIAZEPINONES DE BENZOTHIOPHENE, DE BENZOFURANE ET D'INDOLE, OXAZEPINONES ET DIAZEPINONES UTILISEES COMME INHIBITEURS D'ADHERENCE CELLULAIRE ET DU VIH
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1995024408A1

  公开（公告）日：1995-09-14

  (EN) Benzothiophene, benzofuran and indolethiazepinones, oxazepinones and diazepinones of formula (I) as well as methods of preparation thereof are described as agents which inhibit leukocyte adherence to vascular endothelium and, as such, are effective therapeutic agents for treating inflammatory diseases; these compounds also inhibit the activation of human immunodeficiency virus (HIV).(FR) L'invention concerne des thiazépinones de benzothiophène, de benzofurane et d'indole, des oxazépinones et des diazépinones de la formule (I) ainsi que leurs procédés de production. Ces composés sont utilisés comme inhibiteurs d'adhérence des leucocytes à l'endothélium vasculaire et, constituent, en tant que tels, des principes thérapeutiques efficaces pour traiter les maladies inflammatoires. Ces composés inhibent également l'activation du virus de l'immunodéficience humaine (VIH).

  描述了式(I)的苯并噻吩、苯并呋喃和吲哚噻吩酮、噁唑酮和二氮杂环酮，以及其制备方法，作为抑制白细胞黏附于血管内皮的药物，并且作为治疗炎症性疾病的有效治疗剂；这些化合物还抑制人类免疫缺陷病毒（HIV）的激活。
• Method for inhibiting and controlling viral growth
  申请人：Warner-Lambert Company

  公开号：US05703069A1

  公开（公告）日：1997-12-30

  Benzothiophene, benzofuran and indole-thiazepinones, oxazepinones, and diazepinones are effective therapeutic agents for treating viral diseases, including those caused by herpesvirus and HIV.

  苯并噻吩、苯并呋喃和吲哚-噻唑烷酮、噁唑烷酮和二氮杂噻唑烷酮是治疗病毒性疾病的有效药物，包括由疱疹病毒和HIV引起的疾病。