bis(trifluoromethyl)isocoumarin-3-carboxylate | 128742-89-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: bis(trifluoromethyl)isocoumarin-3-carboxylate
• 英文别名: ethyl 6,7-bis(trifluoromethyl)isocumarin-3-carboxylate；ethyl 6,7-bis(trifluoromethyl)isocoumarin-3-carboxylate；Ethyl-6,7-bis(trifluoromethyl)isocumarin-3-carboxylate；ethyl 1-oxo-6,7-bis(trifluoromethyl)isochromene-3-carboxylate
• CAS: 128742-89-2
• 化学式: C₁₄H₈F₆O₄
• 分子量: 354.206
• InChiKey: CJMPNFUFWCUINL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-Ethoxy-9,10-bis-trifluoromethyl-4,11-dioxa-tricyclo[6.2.1.0^2,7]undeca-2,5,9-triene-5-carboxylic acid ethyl ester 在 氢气 作用下， 以84%的产率得到bis(trifluoromethyl)isocoumarin-3-carboxylate
  参考文献：
  名称：

  Ethyl 6,7-Bis(trifluoromethyl)isocoumarin-3-carboxylate: Formed by a Novel Diels–Alder Cycloaddition Involving Two Different α,β-Unsaturated Esters

  摘要：

  In common with other isocoumarin-based molecules, the planar fused ring system [maximum deviation 0.05(2)Angstrom] in the title molecule, ethyl 1-oxo-6,7-bis(trifluoromethyl)-1H-2-benzopyran-3-carboxylate, C14H8F6O4, contains a non-delocalized double bond [C = C 1.34 (2) Angstrom]. Pairs of molecules form pi-bonded dimers, centred on inversion points at y = 1/4 and 3/4 [closest interplanar C ... C approach 3.59 (3)Angstrom]. Consequently, the crystal structure is composed of alternating aromatic (y = 1/4 or 3/4) and aliphatic zones (y = 0 or 1/2).

  DOI：

  10.1107/s0108270195004781

文献信息

• Some reactions of 3,4-bis(trifluoromethyl)furan and its precursor, 2,3-bis(trifluoromethyl)-7-oxabicyclo[2,2,1]hepta-2,5-diene: novel isocoumarin formation from thermal reaction of the furan with ethyl propynoate
  作者：Aliyu B. Abubakar、Brian L. Booth、Nadia N.E. Suliman、Anthony E. Tipping

  DOI：10.1016/s0022-1139(00)81185-9

  日期：1992.3

  2,2,1]hepta-2,5-diene (2) gives 3,4-bis(trifluoromethyl)furan (1). Treatment of oxanorbornadiene (2) with triflic acid (in CH2Cl2 under reflux) and then with water affords a mixture of 2,3-bis(trifluoromethyl)phenol (4) (6%), tris-(6-trifluoromethylsalicylide) (5) (45%) and 2-trifluoromethyl-6-hydroxybenzoic acid (6) (16%); analogous reaction with conc. sulphuric acid gives only the phenol 4 (44%)

  2,3-双（三氟甲基）-7-氧杂双环[2,2,1]庚-2,5-二烯（2）在450℃下的热解得到3,4-双（三氟甲基）呋喃（1）。用三氟甲磺酸（在CH 2 Cl 2中，在回流条件下）然后用水处理草并降冰片二烯（2），得到2,3-双（三氟甲基）苯酚（4）（6％），三-（6-三氟甲基水杨酸内酯）的混合物（5）（45％）和2-三氟甲基-6-羟基苯甲酸（6）（16％）；与类似的反应。硫酸仅产生苯酚4（44％）。
• Novel Diels-Alder cycloaddition involving two α,β-unsaturated esters in the formation of isocoumarins from the reaction of ethly propynoate with 3,4-bis(trifluoromethy)furan
  作者：Aliyu Balarabe Abubakar、Brian Lewis Booth、Anthony Edgar Tipping

  DOI：10.1016/s0022-1139(00)82385-4

  日期：1990.5

  4-carboxylate (8) in the ratio 52:9, produced by Diels-Alder cycloaddition of the alkyne to the α,β-unsaturated ester function of the initially-formed 1:1 adduct, the oxanorbornadiene (9), followed by opening of the oxygen bridge and elimination of ethanol. The corresponding reaction involving dimethyl acetylenedicarboxylate gives the expected oxanorbornadiene (5).

  丙酸乙酯与3,4-双（三氟甲基）呋喃（4）在150°C下反应，得到6,7-双（三氟甲基）异香豆素-3-羧酸乙酯（7）和相应的4-羧酸酯（8）的混合物）的比例为52：9，这是由炔烃与最初形成的1：1加合物的氧杂硼硼烷二烯（9）的α，β-不饱和酯官能团加成Diels-Alder生成的，然后打开氧桥和消除乙醇。涉及乙炔二羧酸二甲酯的相应反应给出了预期的氧杂降冰片二烯（5）。
• ABUBAKAR, ALIYU BALARABE;BOOTH, BRIAN LEWIS;TIPPING, ANTHONY EDGAR, J. FLUOR. CHEM., 47,(1990) N, C. 353-359
  作者：ABUBAKAR, ALIYU BALARABE、BOOTH, BRIAN LEWIS、TIPPING, ANTHONY EDGAR

  DOI：——

  日期：——