sodium quinoline-2-sulfinate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: sodium quinoline-2-sulfinate
• 英文别名: sodium;quinoline-2-sulfinate
• 化学式: C₉H₆NO₂S*Na
• 分子量: 215.208
• InChiKey: IJBHAESZFRECEA-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.52
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium quinoline-2-sulfinate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 31.17h， 生成 5-[3(4-Chloro-phenyl)-prop-2-ynyl]-5-(quinoline-2-sulfonyl)thiazolidine-2,4-dione
  参考文献：
  名称：

  Novel 5-(3-Aryl-2-propynyl)-5-(arylsulfonyl)thiazolidine-2,4-diones as Antihyperglycemic Agents

  摘要：

  Novel 5-(3-aryl-2-propynyl)-5-(arylsulfonyl)th and 5-(3-aryl-2-propynyl)5-(arylsulfonyl)thiazolidine-2,4-diones were prepared and evaluated as oral antihyperglycemic agents in the obese, insulin resistant db/db mouse model at 100 mg/kg and, if the analogue had sufficient potency, 20 mg/kg. The sulfonylthiazolidinediones, 2, were more potent than the corresponding sulfanylthiazolidinedione congeners, 1. With regard to substituent effects on the 3-propynyl phenyl ring (Ar') of 2,4-halogen, substitution generally resulted in the more potent analogues. Substituent effects on the phenylsulfonyl moiety (Ar) of 2 were less clear, although para-halogen substitution on Ar generally was preferable. 2-Pyridinesulfonyl derivatives (Ar = 2-pyridine in 2) also had good potency. Several compounds from series 2 were effective at lowering glucose and insulin in the obese, insulin resistant ob/ob mouse at the 50 mg/kg oral dose. Compound 20 significantly improved the glucose tolerance of obese, insulin resistant Zucker rats at the 20 mg/kg dose level and had no effect on plasma glucose or on glucose tolerance in normal rats fasted for 18 h at the 100 mg/kg level.

  DOI：

  10.1021/jm9706168
• 作为产物：
  描述：

  2-喹啉硫醇 在 双氧水 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以87%的产率得到sodium quinoline-2-sulfinate
  参考文献：
  名称：

  杂芳基亚磺酸盐与格氏试剂的无过渡金属脱硫交叉偶联

  摘要：

  在无过渡金属的条件下，杂芳基亚磺酸盐与格氏试剂的温和交叉偶联反应已得到发展。这项研究提供了一个SO 2 2 –作为芳族体系中的离去基团的例子，以及构建C–C键的有效方法。

  DOI：

  10.1021/acs.orglett.8b03918

文献信息

• Catalyst Selection Facilitates the Use of Heterocyclic Sulfinates as General Nucleophilic Coupling Partners in Palladium-Catalyzed Coupling Reactions
  作者：Tim Markovic、Benjamin N. Rocke、David C. Blakemore、Vincent Mascitti、Michael C. Willis

  DOI：10.1021/acs.orglett.7b02944

  日期：2017.11.17

  heterocycle-derived sulfinates are shown to be effective nucleophilic coupling partners with aryl chlorides and bromides using Pd(0) catalysis. The use of optimal reaction conditions, specifically incorporating a P(t-Bu)2Me-derived Pd catalyst, allowed reactions to be performed at moderate temperatures and enabled the inclusion of a variety of sensitive functional groups. Challenging heterocyclic sulfinates, including

  一系列5元和6元杂环衍生的亚磺酸盐显示是使用Pd（0）催化与芳基氯化物和溴化物的有效亲核偶联伙伴。使用最佳反应条件，特别是掺入P（t - Bu）2 Me衍生的Pd催化剂，可以在中等温度下进行反应，并可以包含各种敏感的官能团。具有挑战性的杂环亚磺酸盐，包括吡嗪，哒嗪，嘧啶，吡唑和咪唑，均表现出良好的性能。
• Novel 2-substituted alkyl-3-carboxy carbapenems as antibiotics and a method of producing them
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0478874A2

  公开（公告）日：1992-04-08

  The invention relates to new 2-substituted alkyl-3-carboxy carbapenems having the formula: with R1, R2, R3, X and Y defined in the specification as antibiotics and beta lactamase inhibitors produced by a novel Michael addition-elimination reaction of a substituted allyl azetidinone in the reaction shown: with Q defined in the specification.

  本发明涉及新的 2-取代烷基-3-羧基碳青霉烯类，其式如下： R1、R2、R3、X和Y在说明书中定义为抗生素和β-内酰胺酶抑制剂，由取代的烯丙基氮杂环丁酮在如图所示的反应中通过新的迈克尔加成-消除反应生成： Q 的定义见说明书。
• US5068232A
  申请人：——

  公开号：US5068232A

  公开（公告）日：1991-11-26
• US5369102A
  申请人：——

  公开号：US5369102A

  公开（公告）日：1994-11-29
• US5480987A
  申请人：——

  公开号：US5480987A

  公开（公告）日：1996-01-02