4-(1,2,2-trifluorovinyl)benzaldehyde | 1398508-34-3

• 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: 4-(1,2,2-trifluorovinyl)benzaldehyde
• 英文别名: 4-(Trifluorovinyl)benzaldehyde；4-(1,2,2-trifluoroethenyl)benzaldehyde
• CAS: 1398508-34-3
• 化学式: C₉H₅F₃O
• 分子量: 186.133
• InChiKey: MQBDAFPPFVSLQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-溴苯腈 在 甲醇 、 sodium tetrahydroborate 、 copper(l) iodide 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正庚烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 106.17h， 生成 4-(1,2,2-trifluorovinyl)benzaldehyde
  参考文献：
  名称：

  通过构象诱导远程取代对三氟甲基取代基进行选择性脱氟

  摘要：

  三氟甲基取代的苯甲醛及其杂环同系物的酰胺衍生物可以在温和条件下通过远程取代反应选择性环脱氟，水解后得到二氟甲基取代的醛。使用该方法可以进行选择性单脱氟和双脱氟，这提供了生产二氟甲基芳烃的通用途径。

  DOI：

  10.1002/anie.202403477

文献信息

• Palladium-Catalyzed Base-Free Suzuki-Miyaura Coupling Reactions of Fluorinated Alkenes and Arenes via a Palladium Fluoride Key Intermediate
  作者：Masato Ohashi、Hiroki Saijo、Mitsutoshi Shibata、Sensuke Ogoshi

  DOI：10.1002/ejoc.201201405

  日期：2013.1

  activation of fluorinated alkenes and arenes was developed. In this Pd-catalyzed Suzuki–Miyaura-type cross-coupling reaction, neither a base for enhancing the reactivity of the organoboron reagents nor a Lewis acid for promoting C–F bond activation was required. A fluoropalladium intermediate played an essential role in this reaction. In addition, a Ni(NHC) catalyst was efficient for C–C coupling through

  开发了一种通过氟化烯烃和芳烃的 C-F 活化与有机硼酸酯形成 C-C 键的新策略。在这种 Pd 催化的 Suzuki-Miyaura 型交叉偶联反应中，既不需要用于增强有机硼试剂反应性的碱，也不需要用于促进 C-F 键活化的路易斯酸。氟钯中间体在该反应中发挥了重要作用。此外，Ni(NHC)催化剂通过氟芳烃的C-F键活化对C-C偶联是有效的。
• PREPARATION METHOD FOR FLUORINE-CONTAINING OLEFINS HAVING ORGANIC-GROUP SUBSTITUENTS
  申请人：Nagai Takabumi

  公开号：US20130324757A1

  公开（公告）日：2013-12-05

  An object of the present invention is to provide a method that enables the easy and efficient (high yield, high selectivity, low cost) preparation of a fluorine-containing olefin substituted with an organic group or groups from a fluorine-containing olefin. [Solution] The method for preparing a fluorine-containing olefin substituted with an organic group or groups, the method comprising a step of reacting a fluorine-containing olefin with an organic boron compound in the presence of an organic transition metal catalyst containing at least one transition metal selected from the group consisting of nickel, palladium, platinum, rhodium, ruthenium, and cobalt.

  本发明的目的是提供一种方法，能够从含氟烯烃中制备出含有一个或多个有机基团的含氟烯烃，该方法易于且高效（高产率、高选择性、低成本）。 解决方案：制备含有一个或多个有机基团的含氟烯烃的方法，包括在有机过渡金属催化剂的存在下，通过将含氟烯烃与有机硼化合物反应来实现。所述有机过渡金属催化剂包含至少一种过渡金属，所述过渡金属选自镍、钯、铂、铑、钌和钴组成的群体中的一种。
• Copper-mediated One-pot Synthesis of Trifluorostyrene Derivatives from Tetrafluoroethylene and Arylboronate
  作者：Kotaro Kikushima、Hironobu Sakaguchi、Hiroki Saijo、Masato Ohashi、Sensuke Ogoshi

  DOI：10.1246/cl.150322

  日期：2015.7.5

  We developed the copper-mediated synthesis of trifluorostyrene derivatives. β-Fluorine elimination of a 2-aryl-1,1,2,2-tetrafluoroethylcopper complex, generated in situ from arylboronate, copper tert-butoxide, and 1,10-phenanthroline with tetrafluoroethylene (TFE) via carbocupration, was promoted by the addition of a Lewis acid. The present reaction system was applied to the one-pot synthesis of various trifluorostyrene derivatives, through the transmetalation–carbocupration–β-fluorine elimination sequence.

  我们开发了铜介导的三氟苯乙烯衍生物合成方法。由芳基硼酸酯、叔丁醇铜和 1,10-菲罗啉与四氟乙烯（TFE）通过羰基化作用原位生成的 2-芳基-1,1,2,2-四氟乙基铜络合物，在加入路易斯酸的作用下促进了β-氟消除。本反应体系被应用于各种三氟苯乙烯衍生物的一锅合成，反应顺序为反金属化-羰基化-β-氟消除。
• Cross-Linkable Bi-Sulphonyl Derivatives And Their Uses For Preparing Ion-Exchanging Membranes
  申请人：Michot Christophe

  公开号：US20090076178A1

  公开（公告）日：2009-03-19

  The present invention is concerned with novel ion-exchange membranes, their method of preparation and their uses. The membranes are made of a polymer obtained from a monomer or a mixture of bifunctional monomers of general formula [T-SO 2 —Y—SO 2 -T′] − M + . The polymers are useful in an alkali-chloride electrolysis process, as a separator in an electrochemical preparation of inorganic and organic compounds, as a separator between an aqueous and an organic phase, or as a catalyst for Diels-Alder additions, Friedel-Craft reactions, aldol condensations, cationic polymerizations, esterifications, and acetal formations.
• Selective defluorination of trifluoromethyl substituents by conformationally induced remote substitution
  作者：Mehul H. Jesani、Maria Schwarz、Shiwhu Kim、Finlay L. Evans、Alexander White、Alex Browning、Roman Abrams、Jonathan Clayden

  DOI：10.1002/anie.202403477

  日期：——

  Amide derivatives of trifluoromethyl-substituted benzaldehydes, and their heterocyclic congeners, may be selectively cyclodefluorinated by a remote substitution reaction under mild conditions, giving difluoromethyl-substituted aldehydes after hydrolysis. Selective single and double defluorinations are possible using this method, which provides a versatile route to difluoromethyl arenes.

  三氟甲基取代的苯甲醛及其杂环同系物的酰胺衍生物可以在温和条件下通过远程取代反应选择性环脱氟，水解后得到二氟甲基取代的醛。使用该方法可以进行选择性单脱氟和双脱氟，这提供了生产二氟甲基芳烃的通用途径。