(S)-1-[5-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-but-2-en-1-one | 790661-81-3

• 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: (S)-1-[5-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-but-2-en-1-one
• 英文别名: (E)-1-[(2S)-2-(hydroxymethyl)-1-(4-methylphenyl)sulfonyl-2,3-dihydropyrrol-5-yl]but-2-en-1-one
• CAS: 790661-81-3
• 化学式: C₁₆H₁₉NO₄S
• 分子量: 321.397
• InChiKey: KVHWCOCELVKHOB-OOPCZODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-[5-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-but-2-en-1-one 在 三氟乙酸 作用下， 反应 16.0h， 以54 mg的产率得到(2S,4R)-2-hydroxymethyl-4-methyl-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-one
  参考文献：
  名称：

  New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction. 2. Further Studies on the Torquoselectivity

  摘要：

  Conjugated alkoxytrienes in which one of the double bonds is embedded in a heterocyclic moiety are obtained by the Pd-catalyzed coupling reaction of lactam- and lactone-derived vinyl triflates with alpha-alkoxydienylboronates. These compounds undergo a 4pi electrocyclization process (Nazarov reaction) under acidic conditions and afford cyclopenta-fused heterocycles in good yields. As a continuation of a previous study, the torquoselectivity of this Nazarov reaction has been investigated using 2-alkyl-substituted pyrrolidinone and 2- and 4-substituted delta-valerolactone derivatives. High or complete stereoselectivity has only been observed with the 2-alkyl-substituted heterocycles. Both steric and stereoelectronic effects could contribute to determining the stereoselection of the ring closure.

  DOI：

  10.1021/jo0489263
• 作为产物：
  描述：

  (S)-trifluoromethanesulfonic acid 5-(tert-butyl-dimethylsilanyloxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 生成 (S)-1-[5-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-but-2-en-1-one
  参考文献：
  名称：

  New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction. 2. Further Studies on the Torquoselectivity

  摘要：

  Conjugated alkoxytrienes in which one of the double bonds is embedded in a heterocyclic moiety are obtained by the Pd-catalyzed coupling reaction of lactam- and lactone-derived vinyl triflates with alpha-alkoxydienylboronates. These compounds undergo a 4pi electrocyclization process (Nazarov reaction) under acidic conditions and afford cyclopenta-fused heterocycles in good yields. As a continuation of a previous study, the torquoselectivity of this Nazarov reaction has been investigated using 2-alkyl-substituted pyrrolidinone and 2- and 4-substituted delta-valerolactone derivatives. High or complete stereoselectivity has only been observed with the 2-alkyl-substituted heterocycles. Both steric and stereoelectronic effects could contribute to determining the stereoselection of the ring closure.

  DOI：

  10.1021/jo0489263

文献信息

• New Synthetic Approach to Cyclopenta-Fused Heterocycles Based upon a Mild Nazarov Reaction. 2. Further Studies on the Torquoselectivity
  作者：Cristina Prandi、Alessandro Ferrali、Antonio Guarna、Paolo Venturello、Ernesto G. Occhiato

  DOI：10.1021/jo0489263

  日期：2004.10.1

  Conjugated alkoxytrienes in which one of the double bonds is embedded in a heterocyclic moiety are obtained by the Pd-catalyzed coupling reaction of lactam- and lactone-derived vinyl triflates with alpha-alkoxydienylboronates. These compounds undergo a 4pi electrocyclization process (Nazarov reaction) under acidic conditions and afford cyclopenta-fused heterocycles in good yields. As a continuation of a previous study, the torquoselectivity of this Nazarov reaction has been investigated using 2-alkyl-substituted pyrrolidinone and 2- and 4-substituted delta-valerolactone derivatives. High or complete stereoselectivity has only been observed with the 2-alkyl-substituted heterocycles. Both steric and stereoelectronic effects could contribute to determining the stereoselection of the ring closure.