(1,1-difluorononyl)benzene

• 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: (1,1-difluorononyl)benzene
• 英文别名: 1,1-difluorononylbenzene
• 化学式: C₁₅H₂₂F₂
• 分子量: 240.336
• InChiKey: DNZBULQUQSJTQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三氟甲苯 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 、 二氢吡啶 、 三溴化硼 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (1,1-difluorononyl)benzene
  参考文献：
  名称：

  Photoredox-Catalyzed Hydrodifluoroalkylation of Alkenes Using Difluorohaloalkyl Compounds and a Hantzsch Ester

  摘要：

  Photoredox-catalyzed hydrodifluoroalkylation of alkenes proceeded smoothly in the presence of a Hantzsch ester as a hydrogen source under visible light irradiation. The reaction was also applicable to the hydrodifluoroalkylation of alkynes, and a continuous photo flow reaction was also successful.

  DOI：

  10.1021/acs.joc.7b00609

文献信息

• Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes
  作者：Yu-Lan Xiao、Qiao-Qiao Min、Chang Xu、Ruo-Wen Wang、Xingang Zhang

  DOI：10.1002/anie.201601351

  日期：2016.5.4

  A nickel‐catalyzed cross‐coupling between (hetero)arylborons and unactivated 1‐bromo‐1,1‐difluoroalkanes has been developed. The use of two ligands (a bidentate bipyridine‐based ligand, 4,4′‐ditBu‐bpy, and a monodentate pyridine‐based ligand, DMAP) offers a highly efficient nickel‐based catalytic system to prepare difluoroalkylated arenes which have important applications in medicinal chemistry.

  已经开发出了（杂）芳基硼与未活化的1-溴-1,1-二氟烷烃之间镍催化的交叉偶联反应。使用两种配体（基于双联吡啶的配体4,4'-ditBu-bpy和基于单齿吡啶的配体DMAP）提供了高效的镍基催化体系，用于制备在二氟烷基化芳烃中具有重要应用药物化学。
• Bulky Diamine Ligand Promotes Cross-Coupling of Difluoroalkyl Bromides by Iron Catalysis
  作者：Lun An、Yu-Lan Xiao、Shu Zhang、Xingang Zhang

  DOI：10.1002/anie.201802713

  日期：2018.6.4

  iron‐catalyzed cross‐coupling of Grignard reagents with alkyl halides has been well established, the adoption of the reaction for fluoroalkylations has not been reported because traditional catalytic systems often lead to defluorination reactions. Described herein is the investigation of an iron‐catalyzed cross‐coupling between arylmagnesium bromides and difluoroalkyl bromides with modified N,N,N′,N′

  尽管格利雅试剂与烷基卤的铁催化交叉偶联已得到很好的确立，但由于传统的催化体系通常会导致脱氟反应，因此尚未报道采用氟烷基化反应。本文描述了芳基溴化镁与二氟烷基溴化物在N，N，N '，N修饰下的铁催化交叉偶联研究′-四甲基乙烷-1，2-二胺（TMEDA）作为配体。使用这种笨重的二胺（在TMEDA中的乙烯主链的一个碳原子上取代了一个丁烯），可以在温和的反应条件下，与多种二氟烷基溴化物（包括易碎的溴二氟甲烷）进行铁催化的二氟烷基化反应，从而提供了一种通用的方法。以及在药物化学中应用的经济高效的途径。
• METHOD FOR PRODUCING FLUORINATED COMPOUND
  申请人：DAIKIN INDUSTRIES, LTD.

  公开号：US20190071376A1

  公开（公告）日：2019-03-07

  This invention solves the problem of providing an efficient, new method for producing a fluoromethylene-containing compound. The problem can be solved by a method for producing a compound represented by formula (1) or a ring-closed or ring-opened derivative of the compound, wherein R 1 represents an organic group, R X represents hydrogen or fluorine, R 2a , R 2b , R 2c , and R 2d are the same or different, and each represents —Y—R 21 or —N(—R 22 ) 2 , or R 2b and R 2c may join together to form a bond, wherein Y represents a bond, oxygen, or sulfur, R 21 represents hydrogen or an organic group, and R 22 , in each occurrence, is the same or different and represents hydrogen or an organic group; the method comprising step A of reacting a compound represented by formula (2), wherein X represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3), wherein the symbols are as defined above, in the presence of a reducing agent under light irradiation.

  这项发明解决了提供一种用于生产含氟甲烯基化合物的高效新方法的问题。该问题可通过一种用于生产由化学式（1）表示的化合物或该化合物的环闭合或环开放衍生物的方法来解决，其中R1代表有机基团，RX代表氢或氟，R2a、R2b、R2c和R2d相同或不同，每个代表—Y—R21或—N(—R22)2，或者R2b和R2c可以结合形成键，其中Y代表键、氧或硫，R21代表氢或有机基团，每次出现的R22相同或不同，代表氢或有机基团；该方法包括以下步骤：A. 在光照射下，在存在还原剂的条件下，使化学式（2）表示的化合物与化学式（3）表示的化合物发生反应。
• Reductive Conversion of Chlorodifluoromethylbenzene with Samarium(II) Diiodide
  作者：Masato Yoshida、Daiki Suzuki、Masahiko Iyoda

  DOI：10.1246/cl.1994.2357

  日期：1994.12

  PhCF2Cl suffered readily one-electron reduction with SmI2 to give PhCF2 radical and chloride ion. The resulting PhCF2 radical was further reduced with SmI2 to PhCF2SmI2 which reacted with electrophile such as Me3SiCl. The initially formed PhCF2 radical could be trapped by olefin or acetylene before it was reduced to PhCF2SmI2.

  PhCF2Cl 很容易与 SmI2 进行单电子还原，得到 PhCF2 自由基和氯离子。得到的 PhCF2 自由基被 SmI2 进一步还原为 PhCF2SmI2，PhCF2SmI2 与诸如 Me3SiCl 的亲电子试剂反应。最初形成的 PhCF2 自由基可以在被还原为 PhCF2SmI2 之前被烯烃或乙炔捕获。
• Yoshida Masato, Suzuki Daiki, Iyoda Masahiko, Chem. Lett, (1994) N 12, S 2357-2360
  作者：Yoshida Masato, Suzuki Daiki, Iyoda Masahiko

  DOI：——

  日期：——