(Z)-3,3,3-trifluoro-2-(4-methoxyphenyl)-1-fluoro-1-tributylstannylprop-1-ene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-3,3,3-trifluoro-2-(4-methoxyphenyl)-1-fluoro-1-tributylstannylprop-1-ene
• 化学式: C₂₂H₃₄F₄OSn
• 分子量: 509.215
• InChiKey: DASYKKDGECUAEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.33
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-3,3,3-trifluoro-2-(4-methoxyphenyl)-1-fluoro-1-tributylstannylprop-1-ene 在 正丁基锂 、 二乙胺基三氟化硫 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 1,1,1,3,6-pentafluoro-2-(4-methoxyphenyl)-hepta-2E,4E-diene
  参考文献：
  名称：

  A Novel Route to Polyfluorinated Alka-2E,4E-dienes

  摘要：

  用正丁基锂处理(Z)-δ-氟-δ-三氟甲基乙烯基锡 3，得到四氟丙烯阴离子 4，该阴离子与δ、δ-不饱和醛反应，得到 6。在分离或不分离 6 的情况下，加入 DAST 并与 6 反应，只得到多氟化 alka-2E、4E 异构体。值得注意的是，双键的迁移只发生在不含氟的双键上。

  DOI：

  10.1055/s-2004-822326

文献信息

• Stereospecific Synthesis of Trifluoromethylated Vinyl Sulfides
  作者：Yanchang Shen、Guoping Wang

  DOI：10.1055/s-2005-869998

  日期：——

  The synthetic utility of fluorinated vinylstannanes has been explored. This methodology provides a convenient and simple synthesis of trifluoromethylated vinyl sulfides in 60-97% yields with the formation of the E-isomer exclusively. The reaction is stereospecific and of wide scope including various types of thiols (aryl, benzyl, alkyl thiols, and thiols with an ethoxycarbonyl moiety) used as substrates. A possible mechanism is proposed.

  已探讨氟化乙烯基锡化合物的合成实用性。这一方法提供了一种便捷简单的合成三氟甲基乙烯基硫化物的方法，产率为60%-97%，且仅形成E-异构体。该反应具有立体选择性，适用范围广泛，包括多种类型的硫醇（芳香族、苄基、烷基硫醇，以及含乙氧基羧基的硫醇）作为底物。提出了一种可能的机制。
• Synthesis of α-fluoro-β-trifluoromethyl alka-2,4-dienes
  作者：Yanchang Shen、Guoping Wang

  DOI：10.1002/hc.20284

  日期：2007.4

  The palladium/copper(I) iodide cocatalyzed coupling reaction of (Z)-α-fluoro-β-trifluoromethylstannanes (1) with vinyl iodides (2) has been explored giving substituted α-fluoro-β-trifluoromethyl dienes (3) in 33–95% yields. In studies we have conducted so far, a larger number of the configurations of the products remained unchanged (cases 3a, 3e–h), though in several cases (cases 3b–d) two configurations

  (Z)-α-氟-β-三氟甲基锡烷 (1) 与乙烯基碘 (2) 的钯/碘化铜 (I) 共催化偶联反应已被探索在 33 中产生取代的 α-氟-β-三氟甲基二烯 (3) –95% 的产量。在我们迄今为止进行的研究中，大量产品的配置保持不变（案例 3a、3e-h），尽管在一些案例中（案例 3b-d）获得了产品的两种配置。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:208–211, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20284
• A Tandem Nucleophilic Addition, Defluorination and Destannylation. Stereospecific Synthesis of Trifluoromethylated Alkyl and Aryl Vinyl Ethers
  作者：Yanchang Shen、Guoping Wang

  DOI：10.1055/s-2004-831231

  日期：——

  A novel tandem reaction, including nucleophilic addition, defluorination and destannylation reactions, has been found and its application to the stereospecific synthesis of trifluoromethylated alkyl- and aryl vinyl etherswith exclusive formation of E-isomers in 73-96% yields is reported. An Ad N -E mechanism for the tandem reaction leading to alkyl- and aryl vinyl ethers is proposed.

  已经发现了一种新的串联反应，包括亲核加成、脱氟和去烷基化反应，并将其应用于立体有择合成三氟甲基化烷基和芳基乙烯基醚，并以 73-96% 的产率独家形成 E 异构体。提出了一种用于生成烷基和芳基乙烯基醚的串联反应的 Ad N -E 机理。
• Stille cross-coupling reaction of polyfluorovinylstannanes
  作者：Yanchang Shen、Guoping Wang

  DOI：10.1016/j.jfluchem.2003.10.013

  日期：2004.1

  The palladium/copper (I) iodide cocatalyzed coupling reaction of (Z)-alpha-fluoro-beta-trifluoromethylvinylstannanes 1 with aryl iodides 2 and acid chloride 4 has been explored affording substituted (E)-alpha-fluoro-beta-trifluoromethylalkenes 3 and (E)-alpha-fluoro-beta-trifluoromethyl-alpha,beta-unsaturated ketones 5, respectively. The effect of cocatalyst, solvent as well as reaction temperature has been investigated in more detail. The geometric isomers were easily ascertained on the basis of their coupling constant ((4)J(FF)) across the double bond and the retention of the configuration of the products for this conversion was found. (C) 2003 Elsevier B.V. All rights reserved.
• Shen, Yanchang; Wang, Guoping, Synthesis, <hi>2003</hi>, # 2, p. 209 - 212
  作者：Shen, Yanchang、Wang, Guoping

  DOI：——

  日期：——