(R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one | 853356-37-3

• 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: (R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one
• 英文别名: (E)-1-[(2R)-2-but-3-enyl-1-(4-methylphenyl)sulfonyl-2,3-dihydropyrrol-5-yl]-4-methylpent-2-en-1-one
• CAS: 853356-37-3
• 化学式: C₂₁H₂₇NO₃S
• 分子量: 373.516
• InChiKey: GMPONEFEMXOUBL-PSSQXEACSA-N

物化性质

• 沸点：
  508.6±60.0 °C(predicted)
• 密度：
  1.126±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one 在 三氟乙酸 作用下， 反应 20.0h， 以43%的产率得到(2R,4S)-(+)-2-but-3-enyl-4-isopropyl-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-one
  参考文献：
  名称：

  Remote Stereocontrol in the Nazarov Reaction:  A New Approach to the Core of Roseophilin

  摘要：

  Three different procedures are compared to obtain properly substituted divinyl ketones in which one of the double bonds is embedded in a five-membered heterocyclic structure and therefore suitable to produce cyclopenta-fused pyrrole derivatives by the acid-catalyzed Nazarov reaction. These, on treatment with TFA, afforded 2,4-cis-disubstituted 2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-ones with high stereocontrol. One of these Nazarov products was oxidized to the corresponding 4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one derivative, thus obtaining an enantiopure key intermediate in the total synthesis of roseophilin.

  DOI：

  10.1021/jo0504058
• 作为产物：
  描述：

  (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 在 palladium diacetate 正丁基锂 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 40.5h， 生成 (R)-(-)-[5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one
  参考文献：
  名称：

  Remote Stereocontrol in the Nazarov Reaction:  A New Approach to the Core of Roseophilin

  摘要：

  Three different procedures are compared to obtain properly substituted divinyl ketones in which one of the double bonds is embedded in a five-membered heterocyclic structure and therefore suitable to produce cyclopenta-fused pyrrole derivatives by the acid-catalyzed Nazarov reaction. These, on treatment with TFA, afforded 2,4-cis-disubstituted 2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-ones with high stereocontrol. One of these Nazarov products was oxidized to the corresponding 4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one derivative, thus obtaining an enantiopure key intermediate in the total synthesis of roseophilin.

  DOI：

  10.1021/jo0504058

文献信息

• Remote Stereocontrol in the Nazarov Reaction:  A New Approach to the Core of Roseophilin
  作者：Ernesto G. Occhiato、Cristina Prandi、Alessandro Ferrali、Antonio Guarna

  DOI：10.1021/jo0504058

  日期：2005.5.1

  Three different procedures are compared to obtain properly substituted divinyl ketones in which one of the double bonds is embedded in a five-membered heterocyclic structure and therefore suitable to produce cyclopenta-fused pyrrole derivatives by the acid-catalyzed Nazarov reaction. These, on treatment with TFA, afforded 2,4-cis-disubstituted 2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-ones with high stereocontrol. One of these Nazarov products was oxidized to the corresponding 4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one derivative, thus obtaining an enantiopure key intermediate in the total synthesis of roseophilin.