((1R,4S)-4-((4-methyl-N-tosylphenyl)sulfonamido)cyclopent-2-en-1-yl)methyl acetate | 204912-99-2

• 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: ((1R,4S)-4-((4-methyl-N-tosylphenyl)sulfonamido)cyclopent-2-en-1-yl)methyl acetate
• CAS: 204912-99-2
• 化学式: C₂₂H₂₅NO₆S₂
• 分子量: 463.576
• InChiKey: SMWANOBVIAXIPS-VQTJNVASSA-N

物化性质

• 沸点：
  596.927±60.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.380±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.82
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((1R,4S)-4-((4-methyl-N-tosylphenyl)sulfonamido)cyclopent-2-en-1-yl)methyl acetate 在 sodium hydroxide 、 {(i-C3H7O)3P}4Pd 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (+/-)-carbovir
  参考文献：
  名称：

  .pi.-Allylpalladium Formation from Allylic Amines via N,N-Ditosylimides and N-Tosylamides: Efficient Synthesis of the Antiviral Agent Carbovir

  摘要：

  Allylic amines can be easily converted into their N,N-ditosylimides or N-tosylamides which are sufficiently good leaving groups to afford pi-allylpalladium complexes and, hence, with nucleophiles, new allylic systems with retention of configuration. The synthetic utility of this process has been demonstrated by an efficient synthesis of the antiviral agent (+/-)-carbovir,(1) from cyclopentadiene in only seven steps and 13% overall yield.

  DOI：

  10.1021/jo00096a006
• 作为产物：
  描述：

  2-(p-tolylsulfonyl)-2-azabicyclo<2.2.1>hept-5-en-3-one 在 吡啶 、 sodium tetrahydroborate 、 sodium hydride 作用下， 生成 ((1R,4S)-4-((4-methyl-N-tosylphenyl)sulfonamido)cyclopent-2-en-1-yl)methyl acetate
  参考文献：
  名称：

  .pi.-Allylpalladium Formation from Allylic Amines via N,N-Ditosylimides and N-Tosylamides: Efficient Synthesis of the Antiviral Agent Carbovir

  摘要：

  Allylic amines can be easily converted into their N,N-ditosylimides or N-tosylamides which are sufficiently good leaving groups to afford pi-allylpalladium complexes and, hence, with nucleophiles, new allylic systems with retention of configuration. The synthetic utility of this process has been demonstrated by an efficient synthesis of the antiviral agent (+/-)-carbovir,(1) from cyclopentadiene in only seven steps and 13% overall yield.

  DOI：

  10.1021/jo00096a006

文献信息

• ASYMMETRIC SYNTHESIS OF CARBOCYCLIC PYRIMIDINE NUCLEOSIDES VIA π-ALLYLPALLADIUM COMPLEX
  作者：Junxing Shi、Raymond F. Schinazi

  DOI：10.1081/ncn-100002557

  日期：2001.3.31

  Racemic and enantiomerically pure carbocyclic pyrimidine nucleosides were synthesized efficiently by a convergent approach using Trost nucleophilic addition of π-allylpalladium complexes.

  外消旋和对映体纯的碳环嘧啶核苷通过使用Trost亲核加成π-烯丙基铝配合物的收敛方法有效合成。