3-(4,5-dimethyl-thiazol-2-yl)-propionitrile

• 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-(4,5-dimethyl-thiazol-2-yl)-propionitrile
• 英文别名: 3-(4,5-Dimethyl-1,3-thiazol-2-yl)propanenitrile；3-(4,5-dimethyl-1,3-thiazol-2-yl)propanenitrile
• 化学式: C₈H₁₀N₂S
• 分子量: 166.247
• InChiKey: IZFHTMQUXCHCMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4,5-二甲基噻唑 、 丙烯腈 在 [RhCl(coe)2]2 lutidinium chloride 、 三环己基膦 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以59%的产率得到3-(4,5-dimethyl-thiazol-2-yl)-propionitrile
  参考文献：
  名称：

  Intermolecular Coupling of Alkenes to Heterocycles via C−H Bond Activation

  摘要：

  The intermolecular coupling of unactivated alkenes to a range of heterocycles using a Rh(I) catalyst was investigated. A variety of functional groups were incorporated into the alkene, including esters, nitriles, acetals, and phthalimide. Furthermore, the heterocycle tolerated substitution with both electron-rich and electron-deficient groups. The intermolecular coupling became possible after it was discovered that weak acids dramatically increase the rate of both the inter- and intramolecular reactions. An extensive optimization of additives was performed, and HCI.PCY3 (Cy = cyclohexyl) and HCI-P-t-Bu2Et were in general found to be the best additives for the reaction.

  DOI：

  10.1021/jo048666p

文献信息

• Intermolecular Coupling of Isomerizable Alkenes to Heterocycles via Rhodium-Catalyzed C−H Bond Activation
  作者：Kian L. Tan、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja0281129

  日期：2002.11.1

  intermolecular coupling of unactivated alkenes, including isomerizable alkenes, to a range of heterocycles using a Rh(I) catalyst. A variety of functional groups were incorporated, including esters, nitriles, and acetals. The intermolecular coupling became possible after it was discovered that weak acids dramatically increase the rate of both the inter- and intramolecular reactions.

  该报告首次使用 Rh(I) 催化剂将未活化的烯烃（包括可异构化的烯烃）分子间偶联到一系列杂环上。引入了多种官能团，包括酯、腈和缩醛。在发现弱酸显着提高分子间和分子内反应的速率后，分子间偶联成为可能。
• Intermolecular Coupling of Alkenes to Heterocycles via C−H Bond Activation
  作者：Kian L. Tan、Steve Park、Jonathan A. Ellman、Robert G. Bergman

  DOI：10.1021/jo048666p

  日期：2004.10.1

  The intermolecular coupling of unactivated alkenes to a range of heterocycles using a Rh(I) catalyst was investigated. A variety of functional groups were incorporated into the alkene, including esters, nitriles, acetals, and phthalimide. Furthermore, the heterocycle tolerated substitution with both electron-rich and electron-deficient groups. The intermolecular coupling became possible after it was discovered that weak acids dramatically increase the rate of both the inter- and intramolecular reactions. An extensive optimization of additives was performed, and HCI.PCY3 (Cy = cyclohexyl) and HCI-P-t-Bu2Et were in general found to be the best additives for the reaction.