1-<4-<2-(tert-butyldimethylsilyloxy)ethyl>phenyl>-2,2,2-trifluoro-1-ethanone | 73899-16-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-<4-<2-(tert-butyldimethylsilyloxy)ethyl>phenyl>-2,2,2-trifluoro-1-ethanone
• 英文别名: 4-(trifluoroacetyl)phenethoxy-tert-butyldimethylsilane；1-{4-[2-(tert-butyldimethylsilyloxy)ethyl]phenyl}-2,2,2-trifluoro-1-ethanone
• CAS: 73899-16-8
• 化学式: C₁₆H₂₃F₃O₂Si
• 分子量: 332.438
• InChiKey: IAKKCPPDMRCTHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-三氟乙酰基哌啶 、 1-<4-<2-(tert-butyldimethylsilyloxy)ethyl>phenyl>-2,2,2-trifluoro-1-ethanone 在 正丁基锂 作用下， 生成 2-<4-(1-azi-2,2,2-trifluoroethyl)phenyl>ethyl tosylate
  参考文献：
  名称：

  Nassal, Michael, Liebigs Annalen der Chemie, 1983, # 9, p. 1510 - 1523

  摘要：

  DOI：
• 作为产物：
  描述：

  4-溴苯乙醇 在 4-二甲氨基吡啶 、 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-<4-<2-(tert-butyldimethylsilyloxy)ethyl>phenyl>-2,2,2-trifluoro-1-ethanone
  参考文献：
  名称：

  Insecticidal Quinazoline Derivatives with (Trifluoromethyl)diazirinyl and Azido Substituents as NADH:Ubiquinone Oxidoreductase Inhibitors and Candidate Photoaffinity Probes

  摘要：

  Two candidate photoaffinity probes are designed from 4-substituted quinazolines known to be potent insecticides/acaricides and NADH:ubiquinone oxidoreductase inhibitors acting at or near the rotenone site. 4-(11-Azidoundecyl-2-amino)quinazoline, based on the undecylamino analog SAN 548A as a prototype, was synthesized in 18% overall yield from ethyl 10-undecenoate by oxidation of the terminal double bond, reductive amination, coupling to 4-chloroquinazoline, and functional group manipulation of the terminal ethyl ester to an alcohol, a mesylate and finally nucleophilic displacement with azide ions. 4-(4-(3-(Trifluoromethyl)3H-diazirin-3-yl)phenethoxy)quinazoline [the (trifluoromethyl)diazirinyl analog of fenazaquin insecticide/acaricide] was prepared from 4-bromophenethyl alcohol in 31% overall yield by first introducing the trifluoromethylketone moiety followed by its conversion to the (trifluoromethyl)diazirine and finally coupling to 8-chloroquinazoline as above. Both candidate photoaffinity probes have the inhibitory potency of rotenone (IC50 Of 3-4 nM in each case). The azidoundecylamino compound has inadequate photoreactivity whereas that of the (trifluoromethyl)diazirinyl analog is ideal at 350 nm. Radiosynthesis of the latter photoaffinity ligand included introduction of the diazirinyl moiety as the carbene precursor, oxidation of (trifluoromethyl)diazirinylphenethyl alcohol to the corresponding acid with Jones' reagent, and reduction of the phenacetyl chloride intermediate with sodium borotritide to incorporate tritium.

  DOI：

  10.1021/tx9501602