2,2,2-trifluoro-1-(4'-bromo-[1,1'-biphenyl]-4-yl)ethanone | 206758-26-1

• 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: 2,2,2-trifluoro-1-(4'-bromo-[1,1'-biphenyl]-4-yl)ethanone
• 英文别名: 1-(4'-bromo-biphenyl-4-yl)-2,2,2-trifluoroethanone；4-bromo-4'-trifluoroacetylbiphenyl；4-(Trifluoroacetyl)-4'-bromobiphenyl；1-[4-(4-bromophenyl)phenyl]-2,2,2-trifluoroethanone
• CAS: 206758-26-1
• 化学式: C₁₄H₈BrF₃O
• 分子量: 329.116
• InChiKey: JEYJVNRENCIQJH-UHFFFAOYSA-N

物化性质

• 熔点：
  72.5-74.8 °C
• 沸点：
  355.8±37.0 °C(Predicted)
• 密度：
  1.503±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(4'-bromo-[1,1'-biphenyl]-4-yl)ethanone 在 三苯基膦 作用下， 以 二乙二醇二甲醚 为溶剂， 生成 2-<4'-Carbhydroxy-(4-biphenylyl)>-F-propen
  参考文献：
  名称：

  Reaction of crystalline fluoro olefins with bromine vapor

  摘要：

  DOI：

  10.1021/jo00430a023
• 作为产物：
  描述：

  4,4'-二溴联苯 、 三氟乙酸酐 在 tri-n-butyllithium magnesate complex 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以61%的产率得到2,2,2-trifluoro-1-(4'-bromo-[1,1'-biphenyl]-4-yl)ethanone
  参考文献：
  名称：

  Selective metal-halogen exchange of 4,4′-dibromobiphenyl mediated by lithium tributylmagnesiate

  摘要：

  A selective metal-halogen exchange/electrophilic quench protocol on 4.4'-dibromobiphenyl 4 that proceeds under non-cryogenic 0 conditions is reported. This method provides an economic alternative to traditional transition-metal catalyzed cross-coupling chemistry to prepare various biaryls 7a-g. This novel route to functionalized biaryls was used as the basis for the kg-scale preparation of a biphenyl ketone 1, a key intermediate in the synthesis of a potent cathepsin K inhibitor. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.039

文献信息

• Synthesis of Diaziridines and Diazirines via Resin-Bound Sulfonyl Oximes
  作者：Irina Protasova、Bekir Bulat、Nicole Jung、Stefan Bräse

  DOI：10.1021/acs.orglett.6b03252

  日期：2017.1.6

  Diazirines are one of the most prominent functionalities in labeling experiments in vivo and in vitro because they allow photochemical generation of carbenes. The strategy presented herein describes the formation of diaziridines, being essential precursors in diazirine syntheses, using solid-supported procedures with immobilized sulfonyl oximes. The solid-supported building blocks have been shown to

  重氮是体内和体外标记实验中最突出的功能之一，因为它们允许光化学生成碳烯。本文提出的策略描述了使用固相支持的方法与固定的磺酰肟，形成重氮丙啶的方法，该重氮是重氮嗪合成中必不可少的前体。固体支撑的结构单元已被证明是CuAAC和酰胺化反应的有价值的中间体，为构建具有多种功能的复杂化合物提供了可能。
• Asymmetric reductions of (trifluoroacetyl)biphenyl derivatives with bakers' yeast and with Geotrichum candidum acetone powder
  作者：Tamotsu Fujisawa、Yoshio Onogawa、Akira Sato、Takeshi Mitsuya、Makoto Shimizu

  DOI：10.1016/s0040-4020(98)00144-6

  日期：1998.4

  The bakers' yeast reduction of (trifluoroacetyl)biphenyl derivatives produces (R)-trifluoromethyl biphenylyl carbinols in high enantioselectivity, whereas the reduction of the same derivatives with Geotrichum candidum acetone powder gives the corresponding (S)-carbinols in excellent yields and enantioselectivity.

  面包师的酵母还原（三氟乙酰基）联苯衍生物可产生高对映选择性的（R）-三氟甲基联苯基甲醇，而相同的衍生物用Geodrichum candidum丙酮粉末还原可得到相应的（S）羰基化合物，并具有出色的收率和对映选择性。
• Enantiocontrol in the bakers' yeast reduction of trifluoroacetylbiphenyl derivatives
  作者：Tamotsu Fujisawa、Seiji Tanaka、Yoshio Onogawa、Makoto Shimizu

  DOI：10.1016/s0040-4039(99)00052-0

  日期：1999.3

  The bakers' yeast reduction of trifluoroacetyl derivatives was examined in the presence of various esters of methanethiosulfonate. The yeast reduction of 4-bromo-4′-trifluoroacetylbiphenyl using the cyclohexylmethyl methanethiosulfonate resulted in the R product with the highest enantiomeric excess of 96% ee, which is compared with the reduction without the additive to give the corresponding alcohol

  在甲烷硫代磺酸酯的各种酯存在下，检查面包师的酵母还原三氟乙酰基衍生物。使用环己基甲基甲硫代磺酸盐将4-溴-4'-三氟乙酰基联苯进行酵母还原，得到的R产物的对映体过量最高，为96％ee，这与不添加添加剂的还原得到的相应醇的ee含量为84％ee相比。在另一方面，在4- hyrdoxy -4'- trifluoroacetylbiphenyl的情况下，观察到最高的对映选择性也使用环己基甲基methanethiosulfonate，得到[R与90％ee的-product，与减速对比度，而不必添加剂以达到同样的ee为77％的产品。
• Structural effects of the oxazaborolidine derived from L-threonine in the reduction of (trifluoroacetyl)biphenyl derivatives with catecholborane
  作者：Tamotsu Fujisawa、Yoshio Onogawa、Makoto Shimizu

  DOI：10.1016/s0040-4039(98)01237-4

  日期：1998.8

  The reduction of (trifluoroacetyl)biphenyl derivatives with catecholborane as a stoichiometric reductant in the presence of the oxazaborolidine catalyst derived from L-threonine in dichloromethane-toluene at -90 degrees C proceeds to give the corresponding alcohols in high yields with high enantioselectivity: The distinctive feature of this oxazaborolidine exists in the five-membered ring covered with the t-butyldimethylsiloxy group. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Selective metal-halogen exchange of 4,4′-dibromobiphenyl mediated by lithium tributylmagnesiate
  作者：Sarah J. Dolman、Francis Gosselin、Paul D. O'Shea、Ian W. Davies

  DOI：10.1016/j.tet.2006.03.039

  日期：2006.5

  A selective metal-halogen exchange/electrophilic quench protocol on 4.4'-dibromobiphenyl 4 that proceeds under non-cryogenic 0 conditions is reported. This method provides an economic alternative to traditional transition-metal catalyzed cross-coupling chemistry to prepare various biaryls 7a-g. This novel route to functionalized biaryls was used as the basis for the kg-scale preparation of a biphenyl ketone 1, a key intermediate in the synthesis of a potent cathepsin K inhibitor. (c) 2006 Elsevier Ltd. All rights reserved.