3-chloro-4-cyanoisothiazole-5-carboxylic acid | 269400-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-chloro-4-cyanoisothiazole-5-carboxylic acid
• 英文别名: 3-chloro-4-cyano-1,2-thiazole-5-carboxylic acid
• CAS: 269400-52-4
• 化学式: C₅HClN₂O₂S
• 分子量: 188.594
• InChiKey: OTGSSAYMYNTUSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-chloro-4-cyanoisothiazole-5-carboxylic acid 反应 0.25h， 以76%的产率得到3-chloroisothiazole-4-carbonitrile
  参考文献：
  名称：

  New regiospecific isothiazole C–C coupling chemistry

  摘要：

  区域选择性钯催化的偶联反应以良好至高产率实现，从3,5-二氯或3,5-二溴异噻唑-4-腈1和2出发，通过Stille偶联反应得到3-卤代-5-(杂/芳基、烯基和炔基)异噻唑3、4、6–9，通过Sonogashira反应得到3-卤代-5-(杂/芳基炔基)异噻唑14–19，以及通过Ullmann型偶联反应得到5,5'-二(3-氯异噻唑-4-腈)13。3,5-二溴异噻唑-4-腈2比3,5-二氯异噻唑-4-腈1更具反应活性，足以有效进行Stille、Negishi和Sonogashira偶联反应。5,5-二(3-氯异噻唑-4-腈)13通过钯催化的Ullmann偶联反应由3-氯-5-碘异噻唑-4-腈11制备。多种3-取代异噻唑（3-取代基=Cl、Br、OMs、OTs和OTf）反应活性较低，未能成功在异噻唑C-3位置进行Suzuki偶联反应。通过Sandmeyer碘化法制备的3-碘-5-苯基异噻唑-4-腈28成功参与了Suzuki、Ullmann型、Stille、Negishi和Sonogashira偶联反应。所有产物均经过充分表征。

  DOI：

  10.1039/b607442a

文献信息

• ISOTHIAZOLECARBOXYLIC ACID DERIVATIVES
  申请人：NIHON BAYER AGROCHEM K.K.

  公开号：EP1129083A1

  公开（公告）日：2001-09-05
• [EN] ISOTHIAZOLECARBOXYLIC ACID DERIVATIVES<br/>[FR] DERIVES D'ACIDE ISOTHIAZOLECARBOXYLIQUE
  申请人：BAYER AGROCHEM KK

  公开号：WO2000029398A1

  公开（公告）日：2000-05-25

  Novel isothiazolecarboxylic acid derivatives of formula (I) in which X and Y have the meanings given in the specification, processes for the preparation of the new compounds and their use as biocides. New isothiazolecarboxylic acid chlorides of formula (II) in which X has the meanings given in the specification, and a process for the preparation of these compounds.
• New regiospecific isothiazole C–C coupling chemistry
  作者：Irene C. Christoforou、Panayiotis A. Koutentis

  DOI：10.1039/b607442a

  日期：——

  Regioselective palladium catalysed coupling reactions are achieved in good to high yields, starting from either 3,5-dichloro- or 3,5-dibromoisothiazole-4-carbonitriles 1 and 2, providing 3-halo-5-(hetero/aryl, alkenyl and alkynyl)isothiazoles 3, 4, 6–9 from Stille couplings, 3-halo-5-(hetero/arylethynyl)isothiazoles 14–19 from Sonogashira and 5,5′-bi(3-chloroisothiazole-4-carbonitrile) (13) from an Ullmann type coupling. 3,5-Dibromoisothiazole-4-carbonitrile 2 is more reactive than the dichloroisothiazole-4-carbonitrile 1 and effective enough for Stille, Negishi and Sonogashira couplings. 5,5-Bi(3-chloroisothiazole-4-carbonitrile) (13) is prepared by a palladium catalysed Ullmann coupling from 3-chloro-5-iodoisothiazole-4-carbonitrile (11). A variety of 3-substituted isothiazoles (3-substituents = Cl, Br, OMs, OTs and OTf) are less reactive and fail to give successful Suzuki couplings at the isothiazole C-3 position. The 3-iodo-5-phenyl-isothiazole-4-carbonitrile (28), prepared via Sandmeyer iodination, participates successfully in Suzuki, Ullmann type, Stille, Negishi and Sonogashira coupling reactions. All products are fully characterized.

  区域选择性钯催化的偶联反应以良好至高产率实现，从3,5-二氯或3,5-二溴异噻唑-4-腈1和2出发，通过Stille偶联反应得到3-卤代-5-(杂/芳基、烯基和炔基)异噻唑3、4、6–9，通过Sonogashira反应得到3-卤代-5-(杂/芳基炔基)异噻唑14–19，以及通过Ullmann型偶联反应得到5,5'-二(3-氯异噻唑-4-腈)13。3,5-二溴异噻唑-4-腈2比3,5-二氯异噻唑-4-腈1更具反应活性，足以有效进行Stille、Negishi和Sonogashira偶联反应。5,5-二(3-氯异噻唑-4-腈)13通过钯催化的Ullmann偶联反应由3-氯-5-碘异噻唑-4-腈11制备。多种3-取代异噻唑（3-取代基=Cl、Br、OMs、OTs和OTf）反应活性较低，未能成功在异噻唑C-3位置进行Suzuki偶联反应。通过Sandmeyer碘化法制备的3-碘-5-苯基异噻唑-4-腈28成功参与了Suzuki、Ullmann型、Stille、Negishi和Sonogashira偶联反应。所有产物均经过充分表征。