(S)-1-[5-(tert-butyldimethylsilanyloxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one | 853356-50-0

• 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: (S)-1-[5-(tert-butyldimethylsilanyloxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-4-methylpent-2-en-1-one
• 英文别名: (E)-1-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-(4-methylphenyl)sulfonyl-2,3-dihydropyrrol-5-yl]-4-methylpent-2-en-1-one
• CAS: 853356-50-0
• 化学式: C₂₄H₃₇NO₄SSi
• 分子量: 463.714
• InChiKey: SYNFAMLUMPGGFM-ZYEUVFMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.45
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-[5-(tert-butyldimethylsilanyloxymethyl)-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， 生成 (2S,4S)-2-hydroxymethyl-4-isopropyl-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-one 、 (2S,4S)-2-hydroxymethyl-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-(tert-butyldimethylsilanyloxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester 在 正丁基锂 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 28.0h， 生成 (S)-1-[5-(tert-butyldimethylsilanyloxymethyl)-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.