(2E,4E)-5-phenyl-1-pyrrol-1-yl-penta-2,4-dien-1-one | 1021867-76-4

• 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: (2E,4E)-5-phenyl-1-pyrrol-1-yl-penta-2,4-dien-1-one
• 英文别名: (2E,4E)-5-phenyl-1-(1H-pyrrol-1-yl)penta-2,4-dien-1-one；(2E,4E)-5-phenyl-1-pyrrol-1-ylpenta-2,4-dien-1-one
• CAS: 1021867-76-4
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: MGIBOJZRXXCXEA-ZVSIBQGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-phenyl-1-pyrrol-1-yl-penta-2,4-dien-1-one 、 硝基甲烷 在 N-(2-dimethylaminocyclohexyl)-N'-phenyl-thiourea 作用下， 生成 3-nitromethyl-5-phenyl-1-pyrrol-1-yl-pent-4-en-1-one
  参考文献：
  名称：

  基于Epi- Cinchona的硫脲有机催化剂家族作为高效的不对称Michael加成促进剂：硝基链烷烃与查尔酮和α，β-不饱和N-酰基吡咯的对映选择性共轭加成

  摘要：

  A small set of easily available epi-cinchona based thiourea organocatalysts have been synthesized and tested in enantioselective Michael addition of nitroalkanes to chalcones. These bifunctional catalyst systems promoted the conjugate additions with high enantioselectivities and chemical yields. The extension of this methodology was further explored to encompass alpha,beta-unsaturated N-acylpyrroles, as a chalcone mimic. Functionally, the N-acylpyrrole moiety in the adduct acts as an ester surrogate; therefore, it can easily be transformed to various valuable and biologically relevant compounds. This approach allowed the concise stereoselective synthesis of (R)-rolipram.

  DOI：

  10.1021/jo702692a
• 作为产物：
  描述：

  肉桂醛 、 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone 以 甲苯 为溶剂， 反应 24.0h， 以52%的产率得到(2E,4E)-5-phenyl-1-pyrrol-1-yl-penta-2,4-dien-1-one
  参考文献：
  名称：

  基于Epi- Cinchona的硫脲有机催化剂家族作为高效的不对称Michael加成促进剂：硝基链烷烃与查尔酮和α，β-不饱和N-酰基吡咯的对映选择性共轭加成

  摘要：

  A small set of easily available epi-cinchona based thiourea organocatalysts have been synthesized and tested in enantioselective Michael addition of nitroalkanes to chalcones. These bifunctional catalyst systems promoted the conjugate additions with high enantioselectivities and chemical yields. The extension of this methodology was further explored to encompass alpha,beta-unsaturated N-acylpyrroles, as a chalcone mimic. Functionally, the N-acylpyrrole moiety in the adduct acts as an ester surrogate; therefore, it can easily be transformed to various valuable and biologically relevant compounds. This approach allowed the concise stereoselective synthesis of (R)-rolipram.

  DOI：

  10.1021/jo702692a

文献信息

• An Approach for Rapid Increase in Molecular Complexity: Atom Economic Routes to Fused Polycyclic Ring Systems
  作者：Barry M. Trost、Veronika Ehmke

  DOI：10.1021/ol5009872

  日期：2014.5.16

  developed. This process generates alkynyl-substituted cyclopentanes in high yields and diastereo- and enantioselectivities. These chiral precursors are employed for the atom economic assembly of fused polycyclic hydrocarbons with hydroindene, hydroazulene, and hydrocyclopentanaphthalene scaffolds by consecutive cycloaddition reactions.

  已经开发了使用手性双二氨基亚磷酸酯配体的炔基取代的TMM供体和不饱和N-酰基吡咯的不对称三亚甲基甲烷（TMM）[3 + 2]环加成反应的方案。该方法以高收率和非对映和对映选择性产生炔基取代的环戊烷。这些手性前体用于通过连续的环加成反应将稠合的多环烃与氢茚，氢腈和氢环戊萘支架进行原子经济组装。
• <i>Epi</i>-Cinchona Based Thiourea Organocatalyst Family as an Efficient Asymmetric Michael Addition Promoter: Enantioselective Conjugate Addition of Nitroalkanes to Chalcones and α,β-Unsaturated <i>N</i>-Acylpyrroles
  作者：Benedek Vakulya、Szilárd Varga、Tibor Soós

  DOI：10.1021/jo702692a

  日期：2008.5.1

  A small set of easily available epi-cinchona based thiourea organocatalysts have been synthesized and tested in enantioselective Michael addition of nitroalkanes to chalcones. These bifunctional catalyst systems promoted the conjugate additions with high enantioselectivities and chemical yields. The extension of this methodology was further explored to encompass alpha,beta-unsaturated N-acylpyrroles, as a chalcone mimic. Functionally, the N-acylpyrrole moiety in the adduct acts as an ester surrogate; therefore, it can easily be transformed to various valuable and biologically relevant compounds. This approach allowed the concise stereoselective synthesis of (R)-rolipram.