7-(Trifluoromethyl)-7-((trimethylsilyl)oxy)bicyclo<2.2.1>heptane | 160883-03-4

• 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-(Trifluoromethyl)-7-((trimethylsilyl)oxy)bicyclo<2.2.1>heptane
• 英文别名: Trimethyl-[[7-(trifluoromethyl)-7-bicyclo[2.2.1]heptanyl]oxy]silane
• CAS: 160883-03-4
• 化学式: C₁₁H₁₉F₃OSi
• 分子量: 252.352
• InChiKey: YAPNNXACFGYIFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  16
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(Trifluoromethyl)-7-((trimethylsilyl)oxy)bicyclo<2.2.1>heptane 在 盐酸 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 2.0h， 生成 7-(三氟甲基)双环[2.2.1]庚烷-7-醇
  参考文献：
  名称：

  氟化铯用（三氟甲基）三甲基硅烷催化酯，醛和酮的三氟甲基化。

  摘要：

  研究了羧酸酯对（三氟甲基）三甲基硅烷（TMS-CF（3））的低反应性。建立了通用的氟化铯催化亲核三氟甲基化反应的方法。在室温（25摄氏度）下，催化量的氟化铯被发现与羧酸酯反应生成甲硅烷基醚中间体，在水解后得到三氟甲基酮。磺酸酯，亚磺酸酯和亚硒酸酯也显示出良好的反应活性，得到了新颖的三氟甲基化化合物。三氟甲基化方法也适用于醛和酮，将其转化为三氟甲基甲硅烷基醚中间体，并在酸水解后以优异的产率得到三氟甲基化的醇。乙二醇二甲醚用作固体或高沸点底物的溶剂，

  DOI：

  10.1021/jo982494c
• 作为产物：
  描述：

  7-norbornanone 以93%的产率得到
  参考文献：
  名称：

  Nelson Derek W., OReilly Neil J., Speier Jon, Gassman Paul G., J. Org. Chem, 59 (1994) N 26, S 8157-8171

  摘要：

  DOI：

文献信息

• Synthesis and Solvolysis of 7-(Perfluoroalkyl)-7-bicyclo[2.2.1]heptyl Derivatives
  作者：Derek W. Nelson、Neil J. O'Reilly、Jon Speier、Paul G. Gassman

  DOI：10.1021/jo00105a037

  日期：1994.12

  Several alpha-(trifluoromethyl)- and alpha-(pentafluoroethyl)carbinols were synthesized by the addition of perfluoroalkylating agents (TMSCF(3), TMSC(2)F(5), and/or C2F5Li) to polycyclic ketones. An improved procedure for the preparation of alpha-(perfluoroalkyl)trimethylsilyl ethers from (perfluoroalkyl)trimethylsilanes and ketones was developed to facilitate the synthesis of the compounds of interest. All of the alcohols featured the bicyclo[2.2.1]heptyl skeleton or some analog of this structure containing double bonds or cyclopropyl groups. Sulfonate esters of the carbinols were prepared, and these sulfonates were solvolyzed in different solvents to examine the competition between destabilization of the carbocationic intermediates by perfluoroalkyl groups and stabilization by neighboring-group participation. The extent of the destabilization of the cations was gauged by the difference in rates of solvolysis of the alpha-hydrogen and alpha-(perfluoroalkyl) derivatives. The k(alpha-H)/k(alpha-RF) ratios ranged from 8 to similar to 10(4), and the extent of anchimeric assistance that occurred in each system influenced the difference in rates. The pentafluoroethyl group exerted a slightly smaller rate-retarding effect when compared to the trifluoromethyl group (k(alpha-C2F5)/k(alpha-CF3) = 1.1-8.0). The products of the solvolysis reactions revealed a general trend of destabilization of both localized and delocalized cations by perfluoroalkyl groups.
• Nelson Derek W., OReilly Neil J., Speier Jon, Gassman Paul G., J. Org. Chem, 59 (1994) N 26, S 8157-8171
  作者：Nelson Derek W., OReilly Neil J., Speier Jon, Gassman Paul G.

  DOI：——

  日期：——
• Cesium Fluoride Catalyzed Trifluoromethylation of Esters, Aldehydes, and Ketones with (Trifluoromethyl)trimethylsilane
  作者：Rajendra P. Singh、Ganfeng Cao、Robert L. Kirchmeier、Jean'ne M. Shreeve

  DOI：10.1021/jo982494c

  日期：1999.4.1

  low reactivity of carboxylic esters toward (trifluoromethyl)trimethylsilane (TMS-CF(3)) was investigated. A universal cesium fluoride catalyzed procedure for nucleophilic trifluoromethylation was developed. At room temperature (25 degrees C), with catalytic amounts of cesium fluoride, carboxylic esters were found to react to give the silyl ether intermediates, which afforded the trifluoromethyl ketones

  研究了羧酸酯对（三氟甲基）三甲基硅烷（TMS-CF（3））的低反应性。建立了通用的氟化铯催化亲核三氟甲基化反应的方法。在室温（25摄氏度）下，催化量的氟化铯被发现与羧酸酯反应生成甲硅烷基醚中间体，在水解后得到三氟甲基酮。磺酸酯，亚磺酸酯和亚硒酸酯也显示出良好的反应活性，得到了新颖的三氟甲基化化合物。三氟甲基化方法也适用于醛和酮，将其转化为三氟甲基甲硅烷基醚中间体，并在酸水解后以优异的产率得到三氟甲基化的醇。乙二醇二甲醚用作固体或高沸点底物的溶剂，