endo-5-(trifluoromethyl)bicyclo<2.2.1>hept-2-ene | 84029-15-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: endo-5-(trifluoromethyl)bicyclo<2.2.1>hept-2-ene
• 英文别名: (5-endo)-5-(trifluoromethyl)bicyclo[2.2.1]hept-2-ene；endo-5-(trifluoromethyl)bicyclo[2.2.1]hept-2-ene；(1R,4R,5R)-5-(trifluoromethyl)bicyclo[2.2.1]hept-2-ene
• CAS: 84029-15-2
• 化学式: C₈H₉F₃
• 分子量: 162.155
• InChiKey: PBNBTJLQHASCPE-DSYKOEDSSA-N

物化性质

• 沸点：
  121.4±35.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  N,N-diethylbenzeneselenamide 、 endo-5-(trifluoromethyl)bicyclo<2.2.1>hept-2-ene 在 三溴氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以59%的产率得到2-endo-bromo-3-exo-phenylselenenyl-5-endo-(trifluoromethyl)bicyclo[2.2.1]heptane
  参考文献：
  名称：

  Reactions of areneselenenamides with alkenes in the presence of phosphorus(V) and sulfur(IV) oxyhalides. New synthesis of β-haloalkyl selenides

  摘要：

  A new procedure was proposed for activation of areneselenenamides with phosphorus(V) and sulfur(IV) oxyhalides. According to the (1)H, (13)C, and (31)P NMR data, areneselenenamide reacts with phosphorus oxyhalide to form intermediate adduct in which the phosphorus atom is coordinated at the selenium. Areneselenenamides activated by phosphorus(V) oxyhalides react with alkenes (norbornene and norbornadiene) with high trans-stereoselectivity. Their reactions with terminal olefins are regioselective, and they lead to preferential formation of the corresponding Markovnikov adducts.

  DOI：

  10.1134/s1070428009060062
• 作为产物：
  描述：

  3,3,3-三氟丙烯 、 环戊二烯 生成 endo-5-(trifluoromethyl)bicyclo<2.2.1>hept-2-ene
  参考文献：
  名称：

  GAEDE, B.;BALTHAZOR, T. M., J. ORG. CHEM., 1983, 48, N 2, 276-277

  摘要：

  DOI：

文献信息

• New systems for classical nitrosohalogenation of alkenes 1. Reactions of alkenes with ethyl nitrite in the presence of phosphorus halides and thionyl chloride
  作者：O. B. Bondarenko、A. Yu. Gavrilova、V. N. Tikhanushkina、N. V. Zyk

  DOI：10.1007/s11172-006-0088-3

  日期：2005.9

  10-cis-endo-dicarboxylate demonstrated that nitrosation of alkenes with EtONO-PHal3, EtONO-POHal3 (Hal = Cl or Br), and EtONO-SOCl2 systems can afford nitroso halides in high yields without the formation of by-products (ketones and oximes). The reactions with 5-substituted norbornenes are nonregioselective. The trans dimer of endo-5-trifluoromethyl-cis-exo-2-chloro-3-nitrosobicyclo[2.2.1]heptane was studied

  降冰片烯和降冰片二烯衍生物和二甲基三环 [4.2.2.02,5]deca-3,7-diene-9,10-cis-endo-dicarboxylate 的亚硝化研究表明，烯烃与 EtONO-PHal3、EtONO-POHal3（Hal = Cl 或 Br)，EtONO-SOCl2 系统可以高产率提供亚硝基卤化物，而不会形成副产物（酮和肟）。与 5-取代降冰片烯的反应是非区域选择性的。通过X射线衍射研究了endo-5-trifluoromethyl-cis-exo-2-chloro-3-nitrosobicyclo[2.2.1]庚烷的反式二聚体。
• Stereochemistry of the Diels-Alder reaction of cyclopentadiene and 3,3,3-trifluoropropene
  作者：Bruce Gaede、Terry M. Balthazor

  DOI：10.1021/jo00150a031

  日期：1983.1