bis(trifluoromethyl)oxanorbornadiene | 651-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: bis(trifluoromethyl)oxanorbornadiene
• 英文别名: 2,3-Bis(trifluormethyl)-7-oxabicyclo<2.2.1>hepta-2,5-dien；2,3-bis(trifluoromethyl)-7-oxabicyclo<2,2,1>hepta-2,5-diene；2,3-Bis-(trifluormethyl)-7-oxabicyclo<2.2.1>-2,5-heptadien；2,3-bis(trifluoromethyl)-7-oxabicyclo{2.2.1}hepta-2,5-diene；2,3-Bis(trifluoromethyl)-7-oxabicyclo[2.2.1]hepta-2,5-diene
• CAS: 651-91-2
• 化学式: C₈H₄F₆O
• 分子量: 230.11
• InChiKey: MGVLQGGDEXTVKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  bis(trifluoromethyl)oxanorbornadiene 在 lithium aluminium tetrahydride 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 以60%的产率得到1,2-双(三氟甲基)苯
  参考文献：
  名称：

  Synthesis of Benzene Derivatives via Deoxygenation by Low Valent Titanium

  摘要：

  DOI：

  10.1055/s-1984-30976
• 作为产物：
  描述：

  呋喃 、 六氟-2-丁炔 以 四氢呋喃 为溶剂， 反应 6.0h， 以88%的产率得到bis(trifluoromethyl)oxanorbornadiene
  参考文献：
  名称：

  Synthesis of Benzene Derivatives via Deoxygenation by Low Valent Titanium

  摘要：

  DOI：

  10.1055/s-1984-30976

文献信息

• Polyhalogenated heterocyclic compounds. Part 41. Cycloaddition reactions involving hexafluorobut-2-yne and 1,1,1,2,4,4,4-heptafluorobut-2-ene
  作者：Richard D. Chambers、Alex J. Roche、Michael H. Rock

  DOI：10.1039/p19960001095

  日期：——

  Cycloadducts, formed by addition of hexafluorobut-2-yne, may be transformed into bis(trifluoromethyl)-benzene, -phenol and -furan derivatives. Tetrakis(trifluoromethyl)benzene may also be produced. Heptafluorobut-2-ene 2 is also a very efficient dienophile for reactions with cyclopentadiene and furan. Reaction of 2 with furan derivatives at elevated temperatures gives a very effective ‘one pot’ synthesis of 3,4-bis(trifluoromethyl)furan derivatives.

  通过六氟丁-2-炔加成形成的环加成物，可以转化为双(三氟甲基)苯、苯酚和呋喃衍生物。四(三氟甲基)苯也可以合成。七氟丁-2-烯2对于与环戊二烯和呋喃的反应也非常有效。在升高的温度下，2与呋喃衍生物反应可以非常有效地实现3,4-双(三氟甲基)呋喃衍生物的“一锅”合成。
• 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％）。
• Method for Coating the Internal Surface of a Reaction Vessel
  申请人：Brady Frank

  公开号：US20070244324A1

  公开（公告）日：2007-10-18

  The present invention involves the application of ROMP polymers to the internal surfaces of a device for the purpose of carrying out a solid-phase radiochemical process within the device. An additional embodiment of the invention is an automated synthesis system comprising a number of devices of the invention in order that a series of processes can be carried out in direct sequence. In a preferred embodiment, the present invention is a microfabricated device.

  本发明涉及将ROMP聚合物应用于设备的内部表面，以便在设备内进行固相放射化学过程。发明的另一实施例是一种自动合成系统，包括多个该发明的设备，以便一系列过程可以按直接顺序进行。在首选实施例中，本发明是一种微加工设备。
• Prinzbach, Horst; Bringmann, Horst; Markert, Juergen, Chemische Berichte, 1986, vol. 119, # 2, p. 589 - 615
  作者：Prinzbach, Horst、Bringmann, Horst、Markert, Juergen、Fischer, Gerhard、Knothe, Lothar、et al.

  DOI：——

  日期：——
• Living ring-opening metathesis polymerization of 2,3-difunctionalized 7-oxanorbornenes and 7-oxanorbornadienes by Mo(CHCMe2R)(NC6H3-iso-Pr2-2,6)(O-tert-Bu)2 and Mo(CHCMe2R)(NC6H3-iso-Pr2-2,6)(OCMe2CF3)2
  作者：Guillermo C. Bazan、John H. Oskam、Hyun Nam Cho、Lee Y. Park、Richard R. Schrock

  DOI：10.1021/ja00018a028

  日期：1991.8

  7-Oxabenzonorbornadiene (9), 2,3-endo-cis-diacetoxy-7-oxanorbornene, and 2,3-endo-cis-(isopropylidenedioxy)-7-oxanorbornene can be polymerized by Mo(CHCMe2R)(NAr)(O-t-Bu)2 (Ar = 2,6-C6H3-i-Pr2; R = CH3, C6H5) ([Mo]-(CHCMe2R)) to give polymers with narrow molecular weight distributions (PDI < 1.17). However, 2,3-bis(trifluoromethyl)-7-oxanorbornadiene (1), 2,3-dicarbomethoxy-7-oxanorbornadiene (4), and 2,3-trans-dicyano-7-oxanorborn-5-ene (12) form stable metallacycles upon addition to [Mo](CHCMe2R). The rate of reaction of 1 with [Mo](CHCMe2R) has been determined qualitatively to be comparable to that of norbornene in competition experiments, a result that implies that the lone pair on the oxygen in the 7-position is accelerating metallacycle formation. The metallacycle that results from addition of 1 to [Mo](CHCMe2Ph) is square pyramidal with the imido ligand in the apical position. (Crystal data for 2b: a = 12.420 (3) angstrom, b = 15.466 (4) angstrom, c = 20.856 (6) angstrom, V = 3852 (2) angstrom 3, beta = 105.97 (2)degrees, space group = P2(1)/n, Z = 4, M(r) = 779.76, rho = 1.345 g/cm3, mu = 3.9 cm-1, R1 = 0.049, R2 = 0.068.) The MoC3 ring is planar with the CMe2Ph group pointed toward the imido ligand and the C-7 frame of the monomer pointed away from it (a trans metallacyclic ring). The oxygen in the 7-position of the norbornene moiety is located 3.332 (4) angstrom from the metal. Electronic and steric factors that influence first-order breakup of the metallacycle have been studied for monomers 1 and 4. The more reactive catalyst, Mo(CHCMe2Ph)(NAr)(OCMe2CF3)2, can polymerize 1, 4, and 12 to give polymers with narrow molecular weight distributions (PDI < 1.15).