(2E)-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-pyrrol-1-yl-2-propen-1-one | 1021867-77-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (2E)-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-pyrrol-1-yl-2-propen-1-one
• 英文别名: (E)-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-pyrrol-1-ylprop-2-en-1-one
• CAS: 1021867-77-5
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: JXKSPLKDASLSKN-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E)-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-pyrrol-1-yl-2-propen-1-one 、 硝基甲烷 在 N-(2-dimethylaminocyclohexyl)-N'-phenyl-thiourea 作用下， 生成 3-(3-cyclopentyloxy-4-methoxyphenyl)-4-nitro-1-pyrrol-1-yl-butan-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：

  3-环戊氧-4-甲氧基苯甲醛 、 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone 以 甲苯 为溶剂， 反应 24.0h， 以74%的产率得到(2E)-3-(3-cyclopentyloxy-4-methoxyphenyl)-1-pyrrol-1-yl-2-propen-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

• <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.