methyl 3-iodo-4-(methylsulfonamido)benzoate | 851211-49-9

• 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 3-iodo-4-(methylsulfonamido)benzoate
• 英文别名: 3-iodo-4-methanesulfonylamino-benzoic acid methyl ester；methyl 3-iodo-4-(methanesulfonamido)benzoate
• CAS: 851211-49-9
• 化学式: C₉H₁₀INO₄S
• 分子量: 355.153
• InChiKey: CJAGUSSMQPGXKA-UHFFFAOYSA-N

物化性质

• 沸点：
  429.1±55.0 °C(Predicted)
• 密度：
  1.870±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-iodo-4-(methylsulfonamido)benzoate 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-[2-(4-Chloro-phenylsulfanyl)-1-hydroxy-1-methyl-ethyl]-1H-indole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  A bioisosteric approach to the discovery of indole carbinol androgen receptor ligands

  摘要：

  Two potential bioisosteres of the nonsteroidal antiandrogen bicalutamide, an imidazolidinone and an indole, were synthesized and tested for their androgen receptor binding. Indole was discovered to be a suitable bioisostere for the acyl anilide moiety in the parent compound. Several analogs in the indole series were found to be 10-fold better than bicalutamide in binding to the recombinant androgen receptor binding domain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.036
• 作为产物：
  描述：

  4-氨基-3-碘苯甲酸甲酯 在 吡啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 methyl 3-iodo-4-(methylsulfonamido)benzoate
  参考文献：
  名称：

  A bioisosteric approach to the discovery of indole carbinol androgen receptor ligands

  摘要：

  Two potential bioisosteres of the nonsteroidal antiandrogen bicalutamide, an imidazolidinone and an indole, were synthesized and tested for their androgen receptor binding. Indole was discovered to be a suitable bioisostere for the acyl anilide moiety in the parent compound. Several analogs in the indole series were found to be 10-fold better than bicalutamide in binding to the recombinant androgen receptor binding domain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.036

文献信息

• Facile <i>N</i>-Arylation of Amines and Sulfonamides and <i>O</i>-Arylation of Phenols and Arenecarboxylic Acids
  作者：Zhijian Liu、Richard C. Larock

  DOI：10.1021/jo0602221

  日期：2006.4.1

  An efficient, transition-metal-free procedure for the N-arylation of amines, sulfonamides, and carbamates and O-arylation of phenols and carboxylic acids has been achieved by allowing these substrates to react with a variety of o-silylaryl triflates in the presence of CsF. Good to excellent yields of arylated products are obtained under very mild reaction conditions. This chemistry readily tolerates

  通过使这些底物在存在下与多种邻甲硅烷基芳基三氟甲磺酸酯反应，已实现了一种有效的，无过渡金属的胺，磺酰胺和氨基甲酸酯的N-芳基化以及酚和羧酸的O-芳基化方法。的CsF。在非常温和的反应条件下，芳基化产物的收率好至极好。这种化学反应易于耐受各种官能团。
• One-pot Sonogashira coupling, hydroamination of alkyne and intramolecular C H arylation reactions toward the synthesis of indole-fused benzosultams
  作者：Sudarshan Debnath、Shovan Mondal

  DOI：10.1016/j.tetlet.2018.04.081

  日期：2018.6

  A one-pot Sonogashira coupling, hydroamination of alkyne and CH arylation reactions for the synthesis of indole-fused benzosultams are described. This method allows access to a variety of indole-fused seven membered benzosultams in good to excellent yields. The free indolyl nitrogen containing indole-fused benzosultams are also prepared by this method. The structures of the synthesized compounds are

  描述了一锅Sonogashira偶联，炔烃的加氢胺化和C H芳基化反应，用于合成吲哚稠合的苯并舒马坦。该方法允许以良好至优异的产率获得各种吲哚稠合的七元苯并阿磺酰胺。还通过该方法制备了游离的含吲哚基氮的吲哚稠合的苯并硫磺酰胺。通过单晶XRD研究证实了合成化合物的结构。
• Regioselective synthesis of arylsulfonyl heterocycles from bromoallyl sulfones <i>via</i> intramolecular Heck coupling reaction
  作者：Deepak Yadav、Krishna、Sunil K. Sharma、Rajeev S. Menon

  DOI：10.1039/d0ob01623c

  日期：——

  endowed with arylsulfonyl groups were prepared in two steps from 2-bromoallyl sulfones. ortho-Halosulfonamides and ortho-iodophenol reacted with 2-bromoallyl sulfones in the presence of cesium carbonate to furnish products resulting from a formal vinylic substitution reaction. Palladium-catalyzed intramolecular Heck reaction of these adducts furnished sulfonylated indoles, benzosultams and benzofurans

  由 2-溴烯丙基砜分两步制备具有芳基磺酰基的吲哚、苯并呋喃和苯并磺胺。邻-卤代磺酰胺和邻-碘苯酚在碳酸铯存在下与2-溴烯丙基砜反应，得到由正式乙烯基取代反应产生的产物。这些加合物的钯催化分子内 Heck 反应提供磺酰化吲哚、苯并磺胺和苯并呋喃。在碱性条件下，参与 Heck 反应的双键异构化导致在两种情况下形成两种异构产物。开发了选择性进入每个区域异构吲哚的条件。
• Ligand-, copper-, and amine-free one-pot synthesis of 2-substituted indoles via Sonogashira coupling 5-endo-dig cyclization
  作者：Sanjay S. Palimkar、P. Harish Kumar、Rajgopal J. Lahoti、Kumar V. Srinivasan

  DOI：10.1016/j.tet.2006.03.035

  日期：2006.5

  Results of the optimized conditions for the one-pot synthesis of 2-substituted indoles via palladium acetate catalyzed tandem Sonogashira coupling 5-endo-dig cyclization at room temperature under ultrasonic irradiation and standard stirred conditions are described. Electron-donating and electron-withdrawing groups present in both coupling partners were well tolerated under these mild conditions. A

  的用于通过催化串联的Sonogashira乙酸钯耦合5-一锅合成2-取代的吲哚的优化条件下的结果内切-挖超声波照射和标准搅拌的条件下环化在室温下进行了描述。在这种温和条件下，两个偶联配偶体中存在的给电子基团和吸电子基团具有良好的耐受性。无铜，无配体和无胺条件是该方案的重要特征。对于使用超声辐射的反应，观察到反应速率的显着提高。
• NEW INDOLE OR BENZIMIDAZOLE DERIVATIVES AS CB1 INVERSE AGONISTS
  申请人：Bleicher Konrad

  公开号：US20080234290A1

  公开（公告）日：2008-09-25

  Provided are compounds of the formula I: and pharmaceutically acceptable salts thereof, processes for making said compounds and pharmaceutically acceptable salts thereof, pharmaceutical compositions comprising said compound and pharmaceutically acceptable salts thereof, and methods of using said compounds. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with the modulation of CB1 receptors.

  提供的是公式I的化合物及其药学上可接受的盐，制备这些化合物及其药学上可接受的盐的方法，包括这些化合物及其药学上可接受的盐的药物组合物，以及使用这些化合物的方法。这些化合物可用于治疗和/或预防与CB1受体调节相关的疾病。