[(1S,4R)-2-(benzenesulfonyl)-4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-yl] methanesulfonate | 123294-26-8

• 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: [(1S,4R)-2-(benzenesulfonyl)-4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-yl] methanesulfonate
• CAS: 123294-26-8
• 化学式: C₂₈H₃₂O₆S₂Si
• 分子量: 556.776
• InChiKey: HGSYXGKCMGSSCV-GJZUVCINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1S,4R)-2-(benzenesulfonyl)-4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-yl] methanesulfonate 在 氟硼酸钠 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 cis-4-(t-butyldiphenylsilyloxy)-2-phenylsulfonyl-2-cyclopentenyl-1-dimethylsulfonium tetrafluoroborate
  参考文献：
  名称：

  SN2'在砜和酯极化的环戊烯基体系中加成铜酸盐1

  摘要：

  SN2'向砜和酯极化的环戊烯基体系中加入铜酸盐的立体化学显示取决于离去基团的性质。烯丙基铵盐通常会经历立体特异性的界面加成反应。

  DOI：

  10.1016/0040-4020(89)80074-2

文献信息

• Syntheses Via Vinyl Sulfones. 58. A Triply Convergent Total Synthesis of a Symchiral Pyrrolidine-Fused Prostacyclin Analog
  作者：D. C. Smith、P. L. Fuchs

  DOI：10.1021/jo00114a016

  日期：1995.5

  The synthesis of symchiral 1-azatricyclo[6.3.0.0(2,6)]undeca-5-enyl prostaglandin I-2 analog 34 is reported. Construction of the tricyclic skeleton of 34 was accomplished in two steps by employing a triply convergent approach which utilized vinyl sulfone technology. Introduction of the heterocyclic subunit of 34 was achieved by an S(N)2'-thio-Claisen rearrangement which efficiently coupled a thiolactam moiety to a suitable allylic vinyl sulfone. Annulation of bicyclic vinyl sulfones 20, 23, and 29 was accomplished via a conjugate addition of Lithium acetylide 11 to the vinyl sulfone moieties, followed by an intramolecular S(N)2 displacement of a suitable nucleofuge. Competition between intramolecular carbon alkylation and beta-elimination of stabilized nitrogen anions from intermediate a-sulfonyl anions 20-i, 23-i, 29-i was discussed. Refunctionalization of the resulting tricyclic skeleton was accomplished by employing standard literature protocols. Compound 34 was found to be essentially inactive as an inhibitor of collagen-induced platelet aggregation, having an IC50 of > 10 mu M.
• SN2' Additions of cuprates to sulfone and ester-polarized cyclopentenylic systems
  作者：Y. Pan、D.K. Hutchinson、H.H. Nantz、P.L. Fuchs

  DOI：10.1016/0040-4020(89)80074-2

  日期：1989.1

  The stereochemistry of SN2' addition of cuprates to sulfone and ester-polarized cyclopentenyl systems is shown to depend upon the nature of the leaving group. Allyl ammonium salts usually undergo stercospecific synfacial addition reactions.

  SN2'向砜和酯极化的环戊烯基体系中加入铜酸盐的立体化学显示取决于离去基团的性质。烯丙基铵盐通常会经历立体特异性的界面加成反应。