2-chloro-5-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)thiazole | 889672-72-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-chloro-5-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)thiazole
• 英文别名: 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiazole；2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)thiazole；2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)thiazole；2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole
• CAS: 889672-72-4
• 化学式: C₉H₁₃BClNO₂S
• 分子量: 245.538
• InChiKey: UAXMSLFTXSRLPV-UHFFFAOYSA-N

物化性质

• 沸点：
  100 °C(Press: 0.11 Torr)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-5-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)thiazole 、 4-碘氰基苯 在 四(三苯基膦)钯 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.33h， 以27%的产率得到4-(2-氯-5-噻唑)-苯甲腈
  参考文献：
  名称：

  Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions

  摘要：

  Halogenated bithiazoles allow facile further functionalization and are, therefore, suitable intermediates for the synthesis of compounds with interesting biological activity or material science properties. The applicability of three coupling methods (Negishi, Suzuki, and Stille) for the synthesis of the title compounds was compared. The Negishi method proved to be troublesome, and side reactions were predominant. The synthesis of the first thiazoleboronic acid ester offered a new method for the formation of bithiazoles, not generally applicable so far. The lower toxicity compared to that of tin organyls make this method an approach with interesting perspectives. The Stille coupling proved to be superior to the other methods and enabled the synthesis of the title compounds with diverse connectivity.

  DOI：

  10.1021/jo0601009
• 作为产物：
  描述：

  2-氯噻唑 、 频哪醇 在 硼酸三异丙酯 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以86%的产率得到2-chloro-5-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)thiazole
  参考文献：
  名称：

  Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions

  摘要：

  Halogenated bithiazoles allow facile further functionalization and are, therefore, suitable intermediates for the synthesis of compounds with interesting biological activity or material science properties. The applicability of three coupling methods (Negishi, Suzuki, and Stille) for the synthesis of the title compounds was compared. The Negishi method proved to be troublesome, and side reactions were predominant. The synthesis of the first thiazoleboronic acid ester offered a new method for the formation of bithiazoles, not generally applicable so far. The lower toxicity compared to that of tin organyls make this method an approach with interesting perspectives. The Stille coupling proved to be superior to the other methods and enabled the synthesis of the title compounds with diverse connectivity.

  DOI：

  10.1021/jo0601009

文献信息

• Pyrrolopyrazine Kinase Inhibitors
  申请人：Hendricks Robert Than

  公开号：US20110230462A1

  公开（公告）日：2011-09-22

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables n, p, q, Q, X, X′ and Y are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及使用新型吡咯吡嗪衍生物的公式I，其中变量n、p、q、Q、X、X'和Y如本文所述定义，这些衍生物抑制JAK和SYK，并且适用于治疗自身免疫和炎症性疾病。
• Pyrrolopyrazine kinase inhibitors
  申请人：Hendricks Robert Than

  公开号：US08518945B2

  公开（公告）日：2013-08-27

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables n, p, q, Q, X, X′ and Y are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及使用新型吡咯吡嗪衍生物（公式I），其中变量n、p、q、Q、X、X'和Y的定义如本文所述，这些衍生物抑制JAK和SYK，并且对于治疗自身免疫和炎症性疾病有用。
• Halogenated 2‘-Chlorobithiazoles via Pd-Catalyzed Cross-Coupling Reactions
  作者：Peter Stanetty、Michael Schnürch、Marko D. Mihovilovic

  DOI：10.1021/jo0601009

  日期：2006.5.1

  Halogenated bithiazoles allow facile further functionalization and are, therefore, suitable intermediates for the synthesis of compounds with interesting biological activity or material science properties. The applicability of three coupling methods (Negishi, Suzuki, and Stille) for the synthesis of the title compounds was compared. The Negishi method proved to be troublesome, and side reactions were predominant. The synthesis of the first thiazoleboronic acid ester offered a new method for the formation of bithiazoles, not generally applicable so far. The lower toxicity compared to that of tin organyls make this method an approach with interesting perspectives. The Stille coupling proved to be superior to the other methods and enabled the synthesis of the title compounds with diverse connectivity.