2,2,2-三氟-1-(9-菲基)乙酮 | 163082-41-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 2,2,2-三氟-1-(9-菲基)乙酮
• 英文名称: 2,2,2-trifluoro-1-(phenanthren-9-yl) ethan-1-one
• 英文别名: 9-Phenanthryl trifluoromethyl ketone；2,2,2-trifluoro-1-phenanthren-9-ylethanone
• CAS: 163082-41-5
• 化学式: C₁₆H₉F₃O
• 分子量: 274.242
• InChiKey: CTTFSYLJTVALDE-UHFFFAOYSA-N

物化性质

• 沸点：
  386.7±37.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟-1-(9-菲基)乙酮 在 lithium hexamethyldisilazane 、 sodium hydroxide 、 dimethyl sulfide borane 、 盐酸 作用下， 以 四氢呋喃 、 甲苯 、 乙醚 为溶剂， 以64%的产率得到2,2,2-Trifluoro-1-phenanthren-9-yl-ethylamine; hydrochloride
  参考文献：
  名称：

  Unprecedented Catalytic Asymmetric Reduction of N−H Imines

  摘要：

  Addition of lithium bis(trimethylsilyl)amide to perfluorinated ketones 1a-j affords (E)-N-TMS-ketimines 2a-j that are reduced in situ to afford racemic perfluoromethylated amine hydrochloride salts 3a-j in 54-97% yields. Solvolysis of the N-Si bond in MeOH leads to formation of bench-stable, isolable N-H imine Z/E isomer mixtures along with a methanol adduct. Enantioselective reduction of these three-component mixtures provides the first catalytic asymmetric synthesis of trifluoromethylated amines in 72-95% yields and 75-98% ee.

  DOI：

  10.1021/ol047431x
• 作为产物：
  描述：

  t-butyl trifluorothioacetate 、 9-菲硼酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 噻吩-2-甲酸亚铜(I) 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以90%的产率得到2,2,2-三氟-1-(9-菲基)乙酮
  参考文献：
  名称：

  Palladium-catalyzed fluoroacylation of (Hetero)arylboronic acid with fluorothioacetates at ambient temperature

  摘要：

  A palladium-catalyzed fluoroacylation of (hetero)aryl boronic acid with the fluorothioacetates is described at ambient temperature. A variety of aryl, and heteroaryl boronic acids are compatible in the reaction, affording the corresponding fluoroalkyl ketones in moderate to good yields. Further late-stage di-, and trifluoroacylation of drug molecule clofibrate and estrone demonstrated the synthetic practicability of this protocol.2009 Elsevier Ltd. All rights reserved. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.151780

文献信息

• Trifluoromethyl group in the synthesis of heterocyclic compounds: New and efficient synthesis of 3-aryl-4-aminocinnolines
  作者：Alexander S. Kiselyov

  DOI：10.1016/0040-4039(95)00005-w

  日期：1995.2

  A novel base induced transformation of hydrazones 3a-f derived from trifluoromethylaryl ketones and arylhydrazines was found to produce 3-aryl-4-aminocinnolines 4a-g in 52-75% yield. The initial step of the reaction is believed to involve abstraction of Hf from hydrazone.