E-5-(5-ethyl-4,4-dimethyl-pyrrolidin-2-ylidenemethyl)-3,4-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: E-5-(5-ethyl-4,4-dimethyl-pyrrolidin-2-ylidenemethyl)-3,4-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 5-[(E)-(5-ethyl-4,4-dimethyl-3H-pyrrol-2-ylidene)methyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate
• 化学式: C₂₀H₃₀N₂O₂
• 分子量: 330.47
• InChiKey: JSMMGWXEKUYYHS-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-[4,4-Dimethyl-5-methylsulfanyl-3,4-dihydro-pyrrol-(2E)-ylidenemethyl]-3,4-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester 、 ethane,iodozinc(1+) 在 bis-triphenylphosphine-palladium(II) chloride 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以63%的产率得到E-5-(5-ethyl-4,4-dimethyl-pyrrolidin-2-ylidenemethyl)-3,4-dimethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Lewis Acid-Promoted Oxidative Addition of Thioimidates to Pd(0)

  摘要：

  The isomeric S-methyldihydropyrrins 9-Z and 9-E exhibit markedly different behavior in Pd(O)catalyzed cross-coupling reactions. Thioimidates 9-Z are readily converted to imines 10-Z employing Pd(0)/AlkZnI. Under identical conditions 9-E are inert. Oxidative addition to Pd(O) requires activation by Zn or other Lewis acids, which is sterically unfavorable with 9-E. Analogous results were obtained with the related thioimidates 11-E,Z as well as with methylthiopyridines 19alpha-gamma. In the case of both 11 and 19 oxidative addition to Pd(O) was greatly facilitated in the presence of BF3.Et2O. The importance of Lewis acid activation to Pd(O) oxidative addition in such substrates appears to be a general phenomenon not previously recognized.

  DOI：

  10.1021/jo026510o

文献信息

• Lewis Acid-Promoted Oxidative Addition of Thioimidates to Pd(0)
  作者：Indranath Ghosh、Peter A. Jacobi

  DOI：10.1021/jo026510o

  日期：2002.12.1

  The isomeric S-methyldihydropyrrins 9-Z and 9-E exhibit markedly different behavior in Pd(O)catalyzed cross-coupling reactions. Thioimidates 9-Z are readily converted to imines 10-Z employing Pd(0)/AlkZnI. Under identical conditions 9-E are inert. Oxidative addition to Pd(O) requires activation by Zn or other Lewis acids, which is sterically unfavorable with 9-E. Analogous results were obtained with the related thioimidates 11-E,Z as well as with methylthiopyridines 19alpha-gamma. In the case of both 11 and 19 oxidative addition to Pd(O) was greatly facilitated in the presence of BF3.Et2O. The importance of Lewis acid activation to Pd(O) oxidative addition in such substrates appears to be a general phenomenon not previously recognized.