3-chloro-5-(3-nitrophenyl)isothiazole-4-carbonitrile | 647016-63-5

• 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-chloro-5-(3-nitrophenyl)isothiazole-4-carbonitrile
• 英文别名: 4-Isothiazolecarbonitrile, 3-chloro-5-(3-nitrophenyl)-；3-chloro-5-(3-nitrophenyl)-1,2-thiazole-4-carbonitrile
• CAS: 647016-63-5
• 化学式: C₁₀H₄ClN₃O₂S
• 分子量: 265.68
• InChiKey: DTRGHTSNCGJJJM-UHFFFAOYSA-N

物化性质

• 沸点：
  375.4±42.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 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：
  111
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-chloro-5-(3-nitrophenyl)isothiazole-4-carbonitrile 在 一水合肼 作用下， 以 二甲基亚砜 为溶剂， 反应 0.67h， 以90%的产率得到5-amino-3-(3-nitrophenyl)-1H-pyrazole-4-carbonitrile
  参考文献：
  名称：

  The conversion of isothiazoles into pyrazoles using hydrazine

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.06.041
• 作为产物：
  描述：

  3-硝基苯硼酸 、 3,5-二氯-4-异噻唑甲腈 在 palladium diacetate potassium fluoride 、 18-冠醚-6 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以43%的产率得到3-chloro-5-(3-nitrophenyl)isothiazole-4-carbonitrile
  参考文献：
  名称：

  Regiospecific Suzuki coupling of 3,5-dichloroisothiazole-4-carbonitrile

  摘要：

  3,5-二氯异噻唑-4-甲腈 1 与芳基酸和甲基硼酸反应，可以高产 3-氯-5-（芳基和甲基）异噻唑-4-甲腈 2。该反应在碱、相转移剂和钯催化剂方面进行了优化。使用苯基三氟硼酸钾也在 C-5 处实现了高产率的铃木偶联。在 3,5-二溴异噻唑-4-甲腈 4 中，这两种偶联方法都保持了区域特异性，只得到 3-溴-5-苯基异噻唑-4-甲腈 5。在 3-氯-5-苯基异噻唑-4-甲腈 2a 的铃木交叉偶联条件下，得到了独立制备的 3-苯氧基-5-苯基异噻唑-4-甲腈 6，而不是 3-苯基衍生物。所有异噻唑产品均已完全表征。

  DOI：

  10.1039/b306005e

文献信息

• Regiospecific Suzuki coupling of 3,5-dichloroisothiazole-4-carbonitrile
  作者：Irene C. Christoforou、Panayiotis A. Koutentis、Charles W. Rees

  DOI：10.1039/b306005e

  日期：——

  3,5-Dichloroisothiazole-4-carbonitrile 1 reacts with aryl- and methylboronic acids to give in high yields the 3-chloro-5-(aryl and methyl)-isothiazole-4-carbonitrile 2 regiospecifically. The reaction was optimized with respect to base, phase transfer agent and palladium catalyst. Suzuki coupling at C-5 was also achieved in high yield using potassium phenyltrifluoroborate. The regiospecificity of either coupling method is maintained with 3,5-dibromoisothiazole-4-carbonitrile 4 to give exclusively 3-bromo-5-phenylisothiazole-4-carbonitrile 5. Suzuki cross-coupling conditions applied to 3-chloro-5-phenylisothiazole-4-carbonitrile 2a gave 3-phenoxy-5-phenylisothiazole-4-carbonitrile 6, which was prepared independently, and not the 3-phenyl derivative. All isothiazole products were fully characterized.

  3,5-二氯异噻唑-4-甲腈 1 与芳基酸和甲基硼酸反应，可以高产 3-氯-5-（芳基和甲基）异噻唑-4-甲腈 2。该反应在碱、相转移剂和钯催化剂方面进行了优化。使用苯基三氟硼酸钾也在 C-5 处实现了高产率的铃木偶联。在 3,5-二溴异噻唑-4-甲腈 4 中，这两种偶联方法都保持了区域特异性，只得到 3-溴-5-苯基异噻唑-4-甲腈 5。在 3-氯-5-苯基异噻唑-4-甲腈 2a 的铃木交叉偶联条件下，得到了独立制备的 3-苯氧基-5-苯基异噻唑-4-甲腈 6，而不是 3-苯基衍生物。所有异噻唑产品均已完全表征。
• 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.