tetrafluorocyclopentadienone | 73984-72-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tetrafluorocyclopentadienone
• 英文别名: 2,3,4,5-Tetrafluorocyclopenta-2,4-dien-1-one
• CAS: 73984-72-2
• 化学式: C₅F₄O
• mdl: MFCD18812225
• 分子量: 152.048
• InChiKey: PXMSVJAIMNKXHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tetrafluorocyclopentadienone 在 methanolate 、 sodium methylate 作用下， 生成 (4R,5S)-2,3,4,5-tetrafluoro-4-methoxycyclopent-2-en-1-one
  参考文献：
  名称：

  Carbonyl chemistry of tetrafluorocyclopentadienone

  摘要：

  In order to control the Diels-Alder reactivity of the very labile title compound 1, experiments designed to modify the carbonyl group have been carried out. With methanol a hemiketal (4) is formed reversibly at low temperatures, but conjugate addition to give 3-methoxy derivatives 5 and 6 occurs at ordinary temperatures. Diazomethane reacts with 1 in cold methanol to give a spirooxirane (9) which undergoes Diels-Alder dimerization orders of magnitude slower than dienone 1 at room temperature. Hydrogen cyanide gives a cyanohydrin (15) with 1 at low temperatures, but the compound decomposes at 0-degrees-C. Trimethylsilyl cyanide yields the trimethylsilyl cyanohydrin 16, a stable derivative of 1 that dimerizes only at elevated temperatures, yet retains reactivity as a Diels-Alder diene.

  DOI：

  10.1021/jo00001a032
• 作为产物：
  描述：

  tetrafluoro-cyclobut-3-ene-1,2-dicarboxylic acid anhydride 585.0 ℃ 、133.32 Pa 条件下， 生成 tetrafluorocyclopentadienone
  参考文献：
  名称：

  Carbonyl chemistry of tetrafluorocyclopentadienone

  摘要：

  In order to control the Diels-Alder reactivity of the very labile title compound 1, experiments designed to modify the carbonyl group have been carried out. With methanol a hemiketal (4) is formed reversibly at low temperatures, but conjugate addition to give 3-methoxy derivatives 5 and 6 occurs at ordinary temperatures. Diazomethane reacts with 1 in cold methanol to give a spirooxirane (9) which undergoes Diels-Alder dimerization orders of magnitude slower than dienone 1 at room temperature. Hydrogen cyanide gives a cyanohydrin (15) with 1 at low temperatures, but the compound decomposes at 0-degrees-C. Trimethylsilyl cyanide yields the trimethylsilyl cyanohydrin 16, a stable derivative of 1 that dimerizes only at elevated temperatures, yet retains reactivity as a Diels-Alder diene.

  DOI：

  10.1021/jo00001a032

文献信息

• 稠环芳基化合物、有机电子器件及其应用
  申请人：宁波卢米蓝新材料有限公司

  公开号：CN110872310A

  公开（公告）日：2020-03-10

  本发明提供一种稠环芳基化合物、有机电子器件及其应用。所述化合物，具有式(I)或(Ⅱ)所示结构，其中，X1、X2、Y1各自独立地选自由连接键、N和CR6所组成的组合，环A和环B为共轭结构，R1‑R4、R6中任一基团各自独立地与环A或环B以单键、双键连接，和/或R1‑R4、R6中任意相邻的两个之间相互成环C，所述环C为吸电子环，R5选自连接键、R7取代或未取代C6‑C30的芳基、R7取代或未取代C2‑C30的杂芳基，R1‑R4、R6、R7为吸电子基团。本发明化合物分子间无堆叠，提高器件的寿命；取代基为吸电子基团，化合物的LUMO能级在‑4.6～‑6.0eV，可作为P‑掺杂材料。
• New routes to hexafluorocyclopentadiene and related compounds
  作者：Richard R. Soelch、George W. Mauer、David M. Lemal

  DOI：10.1021/jo00350a079

  日期：1985.12
• Perfluorocyclopentadienone
  作者：M. W. Grayston、W. D. Saunders、D. M. Lemal

  DOI：10.1021/ja00521a088

  日期：1980.1
• GRAYSTON M. W.; SAUNDERS W. D.; LEMAL D. M., J. AMER. CHEM. SOC., 1980, 102, NO 1, 413-414
  作者：GRAYSTON M. W.、 SAUNDERS W. D.、 LEMAL D. M.

  DOI：——

  日期：——
• LEMAL, DAVID M.;KLOPOTEK, DAVID L.;WILTERDINK, JANET L.;SAUNDERS, W. DANI+, J. ORG. CHEM., 56,(1991) N, C. 157-160
  作者：LEMAL, DAVID M.、KLOPOTEK, DAVID L.、WILTERDINK, JANET L.、SAUNDERS, W. DANI+

  DOI：——

  日期：——