(Z)-<2-(2-trimethylsilyl-1-ethynyl)-2-cyclopentenylidene>-methyl trifluoromethanesulfonate | 134329-61-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (Z)-<2-(2-trimethylsilyl-1-ethynyl)-2-cyclopentenylidene>-methyl trifluoromethanesulfonate
• CAS: 134329-61-6
• 化学式: C₁₂H₁₅F₃O₃SSi
• 分子量: 324.396
• InChiKey: FFTWFSAKBFIVEE-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (Z)-2-(trifluoromethanesulfonyloxymethylene)cyclopentanone 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 正丁基锂 、 二异丙胺 、 六甲基二硅氮烷 作用下， 反应 4.58h， 生成 (Z)-<2-(2-trimethylsilyl-1-ethynyl)-2-cyclopentenylidene>-methyl trifluoromethanesulfonate
  参考文献：
  名称：

  Scheuplein, Stefan W.; Harms, Klaus; Brueckner, Reinhard, Chemische Berichte, 1992, vol. 125, # 1, p. 271 - 278

  摘要：

  DOI：

文献信息

• Synthetic studies on the compounds related to neocarzinostatin chromophore. 2. Synthesis of the open-chain (E)- and (Z)-dienediyne systems and its application to the synthesis of a strain-released cyclic analogue
  作者：Kazuhiko Nakatani、Katsuko Arai、Kaoru Yamada、Shiro Terashima

  DOI：10.1016/s0040-4020(01)92247-1

  日期：1992.4

  The “double coupling” reaction of the (E)- and (Z)-dienol ditriflates (5 and 6) with various propargyl alcohols was found to give the (E)- and (Z)-dienediyne diols, the open-chain analogues of neocarzinostatin chromophore, stereospecifically. Those (E)- and (Z)-dienediyne diols exhibited comparable cytotoxicity against P388 murine leukemia. The “single coupling” reaction of 6 took place preferentially

  “双耦合”（的反应ë） -和（Ž（）-dienol ditriflates 5和6）与各种炔丙醇被发现，得到（ë） -和（Ž）-dienediyne二醇，开链类似物碳素抑制素生色团的立体定位。这些（E）-和（Z）-二烯二炔二醇对P388鼠类白血病表现出可比的细胞毒性。的“单耦合”反应6发生优先在所述外-环位置得到单烯醇三氟甲磺酸酯，其可以通过与乙炔的第二次偶联反应进一步加工成二烯二炔化合物。该合成方案的应用可以提供新颖的，可释放应变的环状二烯二炔乙缩醛（33）。
• Rapid and stereoselective construction of dienediynes related to the neocarzinostatin chromophore
  作者：Reinhard Brückner、Stefan W. Scheuplein、Jean Suffert

  DOI：10.1016/0040-4039(91)80355-a

  日期：1991.3

  Formylcyclopentanone was transformed into Z configuration dienediynes 15 in three steps. As the key step served Pd catalyzed stereoselective couplings of the isomerically pure bis(enoltriflate) 13 with two equiv. of alkyne.
• Study of the regioselectivity of palladium-catalyzed monocouplings between conjugated bis(enoltriflates) and trimethylsilylacetylene
  作者：Marc Moniatte、Matthias Eckhardt、Kay Brickmann、Reinhard Brückner、Jean Suffert

  DOI：10.1016/s0040-4039(00)73023-1

  日期：1994.3

  The Z-configurated bis(enoltriflates) 2 and 7 were treated at room temperature with TMS acetylene (1.25 equiv.) in the presence of CuI (0. 17 equiv.) and various palladium catalysts (0.07 equiv.), solvents, and amines to afford monocoupling products. Surprisingly, opposite regioselectivities were observed starting from the five-membered (-->8, n = 0) vs. the six-membered bis(enoltriflates) (-->9, n = 1).