3-hydroxy-5-phenylisothiazole-4-carbonitrile | 36778-07-1

• 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: 3-hydroxy-5-phenylisothiazole-4-carbonitrile
• 英文别名: 3-oxo-5-phenyl-2,3-dihydro-isothiazole-4-carbonitrile；3-hydroxy-4-cyano-5-phenyl-isothiazole；3-oxo-5-phenyl-1,2-thiazole-4-carbonitrile
• CAS: 36778-07-1
• 化学式: C₁₀H₆N₂OS
• 分子量: 202.236
• InChiKey: VQCCQZJXURHGBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：
  78.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 3-hydroxy-5-phenylisothiazole-4-carbonitrile 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以86%的产率得到3-trifluoromethanesulfonyloxy-5-phenylisothiazole-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
• 作为产物：
  描述：

  3-氯-5-苯基异噻唑-4-甲腈 在 sodium nitrite 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-hydroxy-5-phenylisothiazole-4-carbonitrile
  参考文献：
  名称：

  异噻唑类。第十五部分。5-硝基异噻唑

  摘要：

  3-甲基-5-硝基异噻唑是由重氮化的5-氨基-3-甲基异噻唑和亚硝酸钠制得的。氧化得到3-羧酸，将其转化为酰胺，腈，醛和衍生物。用亚硝酸钠处理3，5-二氯异噻唑-4-腈，得到3-氯-5-羟基异噻唑-4-腈。

  DOI：

  10.1039/p19720001247

文献信息

• 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。
• Certain isothiazolol esters of phosphorus acids
  申请人：Roussel-UCLAF

  公开号：US03983129A1

  公开（公告）日：1976-09-28

  Novel 3-phosphoryloxy-isothiazoles of the formula ##SPC1## Wherein R is selected from the group consisting of alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms and ##EQU1## R' and R" being individually SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND ALKYL OF 1 TO 3 CARBON ATOMS, R.sub.1 is alkyl of 1 to 3 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, aryl of 6 to 10 carbon atoms, aralkyl of 7 to 12 carbon atoms, cyano, carbalkoxy of 2 to 4 carbon atoms and NHR'", and R'" is selected from the group consisting of hydrogen and aryl of 6 to 10 carbon atoms, R.sub.3 is selected from the group consisting of cyano, alkylthio of 1 to 4 carbon atoms, alkylsulfinyl of 1 to 4 carbon atoms, alkylsulfonyl of 1 to 4 carbon atoms, carbamoyl, carbalkoxy of 2 to 4 carbon atoms and ##EQU2## A and B are individually selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms and X is selected from the group consisting of oxygen and sulfur which have excellent insecticidal properties.

  3-磷酸酯基异噻唑类化合物的结构式如下：##SPC1## 其中R从以下组中选择：1至3个碳原子的烷基，1至3个碳原子的烷氧基和##EQU1## R'和R"分别从以下组中选择：氢和1至3个碳原子的烷基，R.sub.1为1至3个碳原子的烷基，R.sub.2从以下组中选择：氢，1至5个碳原子的烷基，6至10个碳原子的芳基，7至12个碳原子的芳基烷基，氰基，2至4个碳原子的羰基烷氧基和NHR'"，R'"从以下组中选择：氢和6至10个碳原子的芳基，R.sub.3从以下组中选择：氰基，1至4个碳原子的烷硫基，1至4个碳原子的烷基亚硫基，1至4个碳原子的烷基砜基，氨基甲酰基，2至4个碳原子的羰基烷氧基和##EQU2## A和B分别从以下组中选择：氢和1至3个碳原子的烷基，X从以下组中选择：具有优异杀虫性能的氧和硫。
• The conversion of isothiazoles into pyrazoles using hydrazine
  作者：Heraklidia A. Ioannidou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.06.041

  日期：2009.8

  The conversion of isothiazoles into pyrazoles on treatment with hydrazine is investigated. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation are examined. When the isothiazole C-3 substituent is a good nucleofuge, 3-aminopyrazoles are obtained. However, when the 3-substituent is not a leaving group it is retained in the pyrazole product. Treatment of 4-bromo-3-chloro-5-phenylisothiazoie 56 or 3-chloro-4,5-diphenylisothiazole 57 with anhydrous hydrazine at ca. 200 degrees C for a few minutes gives the corresponding 3-hydrazinoisothiazoles 61 and 64 respectively in high yields; the stability of these new hydrazines is investigated. 5,5'-Diphenyl-3,3'-biisothiazole-4,4'-dicarbonitrile 78 reacts with hydrazine to give 5,5'-diphenyl-3,3'-bi(1H-pyi-azole)-4,4'-dicarbonitrile 79. Methylhydrazine reacts with 3-chloro-5-phenytisothiazole-4-carbonitrile 1 to give 3-(1-methylhydrazino)-5-phenylisothiazole-4-carbontrile 83 and 3-amino-lmethyl-5-phenylpyrazole-4-carbonitrile 84. All products are fully characterised and rational mechanisms for the isothiazole into pyrazole transformation are proposed. (C) 2009 Elsevier Ltd. All rights reserved.
• US3983129A
  申请人：——

  公开号：US3983129A

  公开（公告）日：1976-09-28
• Isothiazoles. Part XV. 5-Nitroisothiazoles
  作者：R. J. A. Walsh、K. R. H. Wooldridge

  DOI：10.1039/p19720001247

  日期：——

  3-Methyl-5-nitroisothiazole has been prepared from diazotised 5-amino-3-methylisothiazole and sodium nitrite. Oxidation gave the 3-carboxylic acid, which was converted into the amide, nitrile, aldehyde, and derivatives. Treatment of 3,5-dichloroisothiazole-4-carbonitrile with sodium nitrite gave 3-chloro-5-hydroxyisothiazole-4-carbonitrile.

  3-甲基-5-硝基异噻唑是由重氮化的5-氨基-3-甲基异噻唑和亚硝酸钠制得的。氧化得到3-羧酸，将其转化为酰胺，腈，醛和衍生物。用亚硝酸钠处理3，5-二氯异噻唑-4-腈，得到3-氯-5-羟基异噻唑-4-腈。