7-norbornyl triflate | 25354-43-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 7-norbornyl triflate
• 英文别名: 7-Norbornyltriflat；Bicyclo[2.2.1]heptan-7-yl trifluoromethanesulfonate；7-bicyclo[2.2.1]heptanyl trifluoromethanesulfonate
• CAS: 25354-43-2
• 化学式: C₈H₁₁F₃O₃S
• 分子量: 244.235
• InChiKey: ANXOHPCUZJSHKB-UHFFFAOYSA-N

物化性质

• 沸点：
  63-65 °C(Press: 3 Torr)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-norbornyl triflate 在 2,2,2-三氟乙醇 作用下， 生成 双环[2.2.1]庚烷-7-醇 、 Bicyclo[3.2.0]heptan-2-ol
  参考文献：
  名称：

  Effects of Bridgehead Substitution on Structure and Reactivity of the 7-Norbornyl Cation

  摘要：

  A systematic investigation was undertaken of the effect of bridgehead substitution on the solvolytic reactivity of 7-norbornyl triflates in aqueous TFE. Methyl substitution increases the rate 60-fold and the effect of multiple substitution is additive. Chlorine, on the other hand, exhibits a combined inductive and resonance effect and decreases the reactivity 1700 times. The observed normal secondary P-deuterium isotope effect of the 1,4-d(2) derivative can be rationalized by assuming a tilted C-s geometry for the cationic transition structure which is only slightly higher in energy than the nonclassical intermediate cation of C-1 symmetry. Bridgehead methyl-d(3) kinetic isotope effects are similar to those associated with the nonmigrating methyl group in neopentyl ester solvolyses. These results are in agreement with the recently published structure of the 7-norbornyl cation calculated at the highest ab initio level which has confirmed its nonclassical nature as originally proposed by Winstein.

  DOI：

  10.1021/jo00102a033
• 作为产物：
  描述：

  Trifluoro-methanesulfonic acid (1S,4R,7R)-2,3-bis-trifluoromethyl-bicyclo[2.2.1]hept-2-en-7-yl ester 在 2,2,2-三氟乙醇 作用下， 生成 7-norbornyl triflate
  参考文献：
  名称：

  测试相邻组参与碳正离子形成的对称性。通过三氟甲基取代双键参与的洞察

  摘要：

  Etude cinetique de la solvolyse de 衍生 de l'anti hydroxy-7bicyclo [2.2.1] heptene-2 dans le trifluoro-2,2,2ethanol tamponne a l'aide de lutidine-2,6

  DOI：

  10.1021/ja00327a035

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.2, 1.3.1, page 76 - 99
  作者：

  DOI：——

  日期：——
• Reaction of triflates with potassium diethyl phosphite. Formation of phosphate esters
  作者：Xavier Creary、Brigitte Benage、Kathryn Hilton

  DOI：10.1021/jo00165a019

  日期：1983.8
• Solvolysis of highly unreactive substrates using the trifluoromethanesulfonate (triflate) leaving group
  作者：Tah Mun Su、Wallace F. Sliwinski、Paul Von R. Schleyer

  DOI：10.1021/ja01047a035

  日期：1969.9
• A Simple Method for Determination of Solvolysis Rates by 1H NMR
  作者：Xavier Creary、Ziqi Jiang

  DOI：10.1021/jo00096a073

  日期：1994.8
• CREARY, X.;BENAGE, B.;HILTON, K., J. ORG. CHEM., 1983, 48, N 17, 2887-2891
  作者：CREARY, X.、BENAGE, B.、HILTON, K.

  DOI：——

  日期：——