trans-N-Benzyl-4-(bromomethyl)-3-(tosylmethyl)-2-pyrrolidone | 139591-80-3

• 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: trans-N-Benzyl-4-(bromomethyl)-3-(tosylmethyl)-2-pyrrolidone
• 英文别名: (3R,4R)-1-benzyl-4-(bromomethyl)-3-[(4-methylphenyl)sulfonylmethyl]pyrrolidin-2-one
• CAS: 139591-80-3；139591-81-4
• 化学式: C₂₀H₂₂BrNO₃S
• 分子量: 436.37
• InChiKey: DPMWITGVWOZZBD-PKOBYXMFSA-N

物化性质

• 沸点：
  638.1±55.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-N-Benzyl-4-(bromomethyl)-3-(tosylmethyl)-2-pyrrolidone 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 生成 、 trans-N-Benzyl-4-methyl-3-(tosylmethyl)-2-pyrrolidone
  参考文献：
  名称：

  Chemoselective ring construction from unsymmetrical 1,6-dienes via radical addition of sulfonyl halides

  摘要：

  The sulfonyl radical-promoted cyclizations of 1,6-unsymmetrical dienes can be totally chemoselective. The addition of tosyl halides to various 1,6-dienes bearing both a nucleophilic and an electrophilic double bond clearly indicates that this attractive property is not related to the generally accepted electrophilic nature of tosyl radical. The chemoselectivity is likely to originate from the reversibility of the first step, i.e. tosyl radical addition to the double bond, which favors the formation of the adducts resulting from the one intermediate radical that cyclizes faster.

  DOI：

  10.1021/jo00049a014
• 作为产物：
  描述：

  N-烯丙基苄胺 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 42.0h， 生成 trans-N-Benzyl-4-(bromomethyl)-3-(tosylmethyl)-2-pyrrolidone
  参考文献：
  名称：

  Chemoselective ring construction from unsymmetrical 1,6-dienes via radical addition of sulfonyl halides

  摘要：

  The sulfonyl radical-promoted cyclizations of 1,6-unsymmetrical dienes can be totally chemoselective. The addition of tosyl halides to various 1,6-dienes bearing both a nucleophilic and an electrophilic double bond clearly indicates that this attractive property is not related to the generally accepted electrophilic nature of tosyl radical. The chemoselectivity is likely to originate from the reversibility of the first step, i.e. tosyl radical addition to the double bond, which favors the formation of the adducts resulting from the one intermediate radical that cyclizes faster.

  DOI：

  10.1021/jo00049a014

文献信息

• Chemoselective ring construction from unsymmetrical 1,6-dienes via radical addition of sulfonyl halides
  作者：I. De Riggi、S. Gastaldi、J. M. Surzur、M. P. Bertrand、Albert Virgili

  DOI：10.1021/jo00049a014

  日期：1992.11

  The sulfonyl radical-promoted cyclizations of 1,6-unsymmetrical dienes can be totally chemoselective. The addition of tosyl halides to various 1,6-dienes bearing both a nucleophilic and an electrophilic double bond clearly indicates that this attractive property is not related to the generally accepted electrophilic nature of tosyl radical. The chemoselectivity is likely to originate from the reversibility of the first step, i.e. tosyl radical addition to the double bond, which favors the formation of the adducts resulting from the one intermediate radical that cyclizes faster.