2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propanol | 121591-67-1

• 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-dichloro-3,3,3-trifluoro-1-phenyl-1-propanol
• 英文别名: 2,2-dichloro-3,3,3-trifluoro-1-phenylpropan-1-ol
• CAS: 121591-67-1
• 化学式: C₉H₇Cl₂F₃O
• 分子量: 259.055
• InChiKey: DDAQJZAXZNVKBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propanol 在 甲烷磺酸 、 四乙基对甲苯磺酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(三氟甲基)苯乙酮
  参考文献：
  名称：

  Electroreductive coupling of halofluoro compounds with aldehydes

  摘要：

  Electroreductive intermolecular coupling of halofluoro compounds such as 1,1,1-trichloro-2,2,2-trifluoroethane, methyl chlorodifluoroacetate, and perfluoroalkyl halides with aldehydes took place effectively in the presence of chlorotrimethylsilane and one of the coupling products, 2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propanol, was selectively convertible to a variety of compounds with using the electroreduction as a key reaction.

  DOI：

  10.1016/0040-4039(91)80223-s
• 作为产物：
  描述：

  2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propyl acetate 在 cellulase (Trichoderma viride) enzyme 、 lipase P enzyme 作用下， 以 水 为溶剂， 反应 182.0h， 生成 2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propanol
  参考文献：
  名称：

  The synthesis of optically active building blocks carrying an α, α-dihalogeno-β, β, β-trifluoroethyl group

  摘要：

  DOI：

  10.1016/s0022-1139(00)83963-9

文献信息

• Fluorine-Containing Organozinc Reagents Part 1 A Simple Synthesis of 2,2-Dichloro-3,3,3-trifluoropropanol
  作者：Robert Werner Lang

  DOI：10.1002/hlca.19860690415

  日期：1986.6.18

  The title compound 1, which can be regarded as a synthetic equivalent of substituted 1,1,1-trifluoroacetone 2, is prepared by Zn-induced reductive addition of 1,1,1-trichloro-2,2,2-trifluoroethane (3) to formaldehyde (4). A brief survey of the scope of this CC-bond formation leading to a variety of new CF3-containing synthetic building blocks is also given.

  标题化合物1（可以视为取代的1,1,1-三氟丙酮2的合成等价物）是通过Zn诱导的1,1,1-三氯-2,2,2-三氟乙烷（3）的还原性加成反应制得的（3）转化为甲醛（4）。还简要概述了这种CC键形成的范围，从而导致了各种新型的含CF 3的合成构件。
• A Facile Stereoselective Synthesis of (<i>E</i>)-1-Aryl-1,2,3,3,3-pentafluoropropenes and (<i>E</i>)-1-Aryl-2-chloro-1,3,3,3-tetrafluoropropenes
  作者：Manabu Kuroboshi、Tamejiro Hiyama

  DOI：10.1246/cl.1990.1607

  日期：1990.9

  ArCH(OH)CX2CF3 whose hydroxyl group was substituted by fluorine. Dehydrohalogenation of the resultant ArCHFCX2CF3 (X = Cl or F) with DBU or NaNH2/t-BuOH (cat) gave with excellent selectivity the title (E)-propenes.

  芳烃甲醛 ArCHO 与类碳化试剂 CF3CX2Mtl（X = Cl，Mtl = ZnCl；X = F，Mtl = Li）反应，得到加合物 ArCH(OH)CX2CF3，其羟基被氟取代。用 DBU 或 NaNH2/t-BuOH (cat) 对所得 ArCHFCX2CF3 (X = Cl 或 F) 进行脱卤化氢反应，以极好的选择性得到标题 (E)-丙烯。
• Synthesis of 1-Aryl-3,3,3-trifluoro-1-propynes and 3,5-Diaryl-4- trifluoromethylisoxazoles
  作者：Giovanni Meazza、Luigi Capuzzi、Paolo Piccardi

  DOI：10.1055/s-1989-27247

  日期：——

  Diaryl-substituted trifluoromethylisoxazoles 5a-i,6a-c, and 6e-i are synthesized from aromatic nitrile oxides and various substituted 1-aryl-3,3,3-trifluoro-1-propynes.

  二芳基取代的三氟甲基异噁唑 5a-i、6a-c 和 6e-i 是由芳香族腈氧化物和各种取代的 1-芳基-3,3,3-三氟-1-丙炔合成的。
• Practical, Stereocontrolled Synthesis of Polyfluorinated Artificial Pyrethroids
  作者：Makoto Fujita、Kiyosi Kondo、Tamejiro Hiyama

  DOI：10.1246/bcsj.60.4385

  日期：1987.12

  Practical and stereocontrolled approaches to polyfluorinated synthetic pyrethroids based on aldehyde addition of CF3CCl2ZnCl are described. The zinc reagent was allowed to react with 3-formyl-2,2-dimethylcyclopropanecarboxylates (6) to give the corresponding adducts. These were acetylated and then reduced again with zinc to afford (1R*, 3S*)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates (12). The (1R*, 3R*)-isomer was derived from 2,2-dichloro-1,1,1-trifluoro-5-methyl-4-hexen-3-ol by diazoacetylation, Cu(II)-catalyzed intramolecular carbene addition, and finally by the zinc reduction. An alternative access to 12 and its halogen homologues of the (Z)-pyrethroids involves addition of 1-halo-2,2-difluoroethenyl group across the CHO group of 6 and subsequent regio- and stereoselective halogenation.

  本文介绍了基于 CF3CCl2ZnCl 的醛加成法制备多氟合成拟除虫菊酯的实用立体控制方法。锌试剂可与 3-甲酰基-2,2-二甲基环丙烷羧酸盐 (6) 反应，生成相应的加合物。这些加合物经乙酰化后再次用锌还原，得到 (1R*，3S*)-3-(2-氯-3,3,3-三氟-1-丙烯基)-2,2-二甲基环丙烷羧酸盐 (12)。(1R*, 3R*)异构体是由 2,2-二氯-1,1,1-三氟-5-甲基-4-己烯-3-醇通过重氮乙酰化、Cu(II)催化的分子内碳烯加成，最后通过锌还原得到的。获得 12 及其 (Z)- 吡咯烷卤素同系物的另一种方法是在 6 的 CHO 基上添加 1-卤代-2,2-二氟乙烯基，然后进行区域和立体选择性卤化。
• Efficient carboncarbon bond formation with thermally stable 1,1-dihalo-2,2,2-trifluoroethylzinc reagent
  作者：Makoto Fujita、Tomoe Morita、Tamejiro Hiyama

  DOI：10.1016/s0040-4039(00)84468-8

  日期：1986.1

  The zinc carbenoids CF3CX2ZnX, prepared from CF3CX3 and zinc powder in dimethylformamide, were found thermally stable to add to aldehyde carbonyls in excellent yields.

  发现由CF 3 CX 3和锌粉在二甲基甲酰胺中制得的类锌锌CF 3 CX 2 ZnX具有很高的热稳定性，可以高产率地添加到羰基醛中。