2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanophenone | 78960-66-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanophenone
• 英文别名: phenyl(F-hexyl)-cetone；(Perfluoroheptanoyl)benzene；n-perfluorohexyl phenyl ketone；2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-1-phenylheptan-1-one
• CAS: 78960-66-4
• 化学式: C₁₃H₅F₁₃O
• 分子量: 424.161
• InChiKey: WEZRUJCIUIEOFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoroheptanophenone 在 sulfur tetrafluoride 作用下， 生成 pentadecafluoroheptylbenzene
  参考文献：
  名称：

  Preparation and properties of perflouroalkylated benzene sulfonates

  摘要：

  DOI：

  10.1016/s0022-1139(00)83354-0
• 作为产物：
  描述：

  溴化锂 以7%的产率得到
  参考文献：
  名称：

  UNO, HIDEMITSU;SHIRAISHI, YASUKAZU;SHIMOKAWA, KAZUHIRO;SUZUKI, HITOMI, CHEM. LETT.,(1988) N 4, 729-732

  摘要：

  DOI：

文献信息

• Boron Trifluoride-Assisted Reaction of Perfluoroalkyllithiums with Imines. A Novel Route to Perfluoroalkylated Amines
  作者：Hidemitsu Uno、Yasukazu Shiraishi、Kazuhiro Shimokawa、Hitomi Suzuki

  DOI：10.1246/cl.1988.729

  日期：1988.4.5

  In the presence of BF3, perfluoroalkyllithiums were found to react with imines to give perfluoroalkylated amines in moderate to good yields.

  在 BF3 存在下，发现全氟烷基锂与亚胺反应以中等至良好的产率得到全氟烷基化胺。
• Sc(OTf)₃-Catalyzed C2-Selective Cyanation/Defluorination Cascade of Perfluoroalkylated 3-Indolylmethanols and Application to the Synthesis of 3-Fluoro(perfluoroalkyl)-β-carbolines
  作者：Jingjing Sang、Li Feng、Rui Hu、Jichao Chen、Dandan Shang、Qing Bao、Weidong Rao

  DOI：10.1021/acs.orglett.1c02932

  日期：2021.10.1

  perfluoroalkylated 3-indolylmethanols with TMSCN is described, which provides a novel and practical strategy for the synthesis of structurally diverse 3-(2-cyano)-indolyl substituted gem-difluoroalkenes and β-fluoro-β-perfluoroalkylalkenes. The reaction features excellent regio- and stereoselectivity and broad substrate scope. Notably, the obtained gem-difluoroalkenes and β-fluoro-β-perfluoroalkylalkenes

  描述了一种前所未有的 Sc(OTf) 3催化 C2 选择性氰化/脱氟级联的全氟烷基化 3-吲哚甲醇与 TMSCN，这为合成结构多样的 3-(2-氰基)-吲哚基取代的宝石提供了一种新颖实用的策略-二氟烯烃和β-氟-β-全氟烷基烯烃。该反应具有优异的区域和立体选择性和广泛的底物范围。值得注意的是，得到的钆-二氟烯烃和β-氟-β-全氟烷基烯烃可以很容易地转化为3-氟（全氟烷基）-β-咔啉，只需在温和的反应条件下用格氏试剂或DIBAL-H处理即可。
• The Reaction of Carboxylic Acid Esters with RfMgBr: A Convenient Synthesis of Perfluoroalkyl Ketones
  作者：Can Xue、Guangke He、Chunling Fu、Liqin Xue、Zhenyang Lin、Shengming Ma

  DOI：10.1002/ejoc.201000887

  日期：2010.12

  synthetically attractive perfluoroalkyl ketones through the reaction of readily available alkenoates, alkynoates, or regular carboxylic esters with perfluoroalkyl Grignard reagents at -70 to -60 °C in diethyl ether with moderate to good yields was developed. The reaction stopped at the ketone stage, with no further reaction to form the tertiary alcohols being observed. DFT calculations confirmed that

  开发了一种通过容易获得的烯酸酯、炔酸酯或常规羧酸酯与全氟烷基格氏试剂在 -70 至 -60 °C 下在二乙醚中反应以中等至良好产率制备具有合成吸引力的全氟烷基酮的有效方法。反应在酮阶段停止，没有观察到进一步反应形成叔醇。DFT 计算证实，与普通酮相比，全氟烷基取代的酮的亲电性较低。
• Asymmetric Construction of Fluoroalkyl Tertiary Alcohols through a Three-Component Reaction of (Bpin)₂, 1,3-Enynes, and Fluoroalkyl Ketones Catalyzed by a Copper(I) Complex
  作者：Xu-Cheng Gan、Qi Zhang、Xue-Shun Jia、Liang Yin

  DOI：10.1021/acs.orglett.7b04039

  日期：2018.2.16

  An asymmetric three-component reaction of Bis(pinacolato)diboron ((BPin)2), 1,3-enynes, and fluoroalkyl ketones was carried out by using a copper(I)-Ph-BPE complex as the catalyst, which afforded a series of chiral fluoroalkyl diols in good to high yield, good to high diastereoselectivity, and high enantioselectivity after an oxidative workup. The reaction exhibits advantages that include a broad substrate

  以铜（I）-Ph-BPE络合物为催化剂，进行了双（频哪醇）二硼（（BPin）2），1,3-烯炔和氟代烷基酮的不对称三组分反应。系列的手性氟烷基二醇具有良好的高收率，良好的高非对映选择性以及氧化后的高对映选择性。该反应展现出的优点包括广泛的底物范围，高官能团相容性，高立体选择性和容易的反应方案。该反应的合成效用通过几次转化得以展示。
• Re-investigation of the Coupling Reaction of 2-Aryl-1,1-dibromo-3,3,3-trifluoropropenes. Preparation of Perfluoroalkylated [3]Cumulenes
  作者：Hidemitsu Uno、Nobumasa Nibu、Noboru Misobe

  DOI：10.1246/bcsj.72.1365

  日期：1999.6

  The coupling reaction of perfluoroalkylated 2-aryl-1,1-dibromoalkenes using zinc and copper(I) bromide gave stereoisomeric mixtures of [3]cumulenes and [4]radialenes. The ratio of [3]cumulenes and [4]radialenes mainly depended upon the reaction temperature and the electronic character of the aryl group. When the coupling reaction was carried out at −40 °C, (E)- and (Z)-[3]cumulenes were obtained in good selectivity and only trace amounts of [4]radialenes were detected by a 19F NMR analysis. On the other hand, a similar reaction at −60 °C afforded a considerable amount of [4]radialene isomers. When the cis-[3]cumulenes were heated at an appropriate temperature, selective isomerization to trans-[3]cumulenes occurred.

  使用锌和溴化铜(I)进行全氟烷基化的2-芳基-1,1-二溴烯偶联反应生成了[3]累烯和[4]放射烯的立体异构混合物。[3]累烯和[4]放射烯的比例主要依赖于反应温度和芳基的电子特性。当在-40 °C进行偶联反应时，获得了良好选择性的(E)-和(Z)-[3]累烯，仅在氟-19核磁共振分析中检测到微量的[4]放射烯。另一方面，在-60 °C进行类似反应时，产生了相当数量的[4]放射烯异构体。当顺式-[3]累烯在适当温度下加热时，会发生选择性异构化转化为反式-[3]累烯。