diethoxy(methyl)carbenium tetrafluoroborate | 21872-75-3

• 英文名称: diethoxy(methyl)carbenium tetrafluoroborate
• 英文别名: diethoxymethylcarbenium tetrafluoroborate；methyldiethoxycarbenium tetrafluoroborate；Diethoxymethylcarbenium-tetrafluoroborat；methyldiethoxycarbenium fluoroborate
• CAS: 21872-75-3；102651-94-5
• 化学式: BF₄*C₆H₁₃O₂
• 分子量: 203.973
• InChiKey: WJFMUXBIUXFXQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  diethoxy(methyl)carbenium tetrafluoroborate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以14%的产率得到ethyl 3,5,5-triethoxy-2-hexenoate
  参考文献：
  名称：

  Procedure for diethoxymethylation of ketones

  摘要：

  DOI：

  10.1021/jo00325a023
• 作为产物：
  描述：

  原乙酸三乙酯 在 tetrafluoroboric acid 作用下， 以 乙醚 为溶剂， 以94%的产率得到diethoxy(methyl)carbenium tetrafluoroborate
  参考文献：
  名称：

  Regioselective, mild acylation of 2-methylindole with di- and trialkoxycarbenium tetrafluoroborates?A simple procedure for deriving 3-acyl-2-methyl-indoles and 3-methoxycarbonyl-2-methylindole

  摘要：

  DOI：

  10.1007/bf00816532

文献信息

• Flo, Camran; Pindur, Ulf, Liebigs Annalen der Chemie, 1987, p. 509 - 514
  作者：Flo, Camran、Pindur, Ulf

  DOI：——

  日期：——
• Pindur, Ulf; Flo, Camran; Akguen, Eyuep, Liebigs Annalen der Chemie, 1986, # 9, p. 1621 - 1627
  作者：Pindur, Ulf、Flo, Camran、Akguen, Eyuep、Tunali, Mustafa

  DOI：——

  日期：——
• Pindur, U.; Flo, C., Synthetic Communications, 1989, vol. 19, # 13-14, p. 2307 - 2312
  作者：Pindur, U.、Flo, C.

  DOI：——

  日期：——
• Pindur, U.; Flo, C., Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1563 - 1568
  作者：Pindur, U.、Flo, C.

  DOI：——

  日期：——
• Lactones. 3. A comparison of the basicities of lactones and esters
  作者：Kenneth B. Wiberg、Roy F. Waldron

  DOI：10.1021/ja00020a037

  日期：1991.9

  The basicity of lactones and esters toward triethyloxonium ion was studied via NMR spectroscopy. The equilibrium constants were measured, and the order of decreasing basicity was found to be delta-valerolactone > gamma-butyrolactone > diethyl carbonate > ethyl acetate > ethyl propionate. The rates of reaction were parallel to the equilibrium constants. The origin of the differences in basicity was explored via ab initio calculations of structures and energies of ions formed by adding H+ or CH3+ to methyl acetate. The calculated proton affinity of the Z ester rotamer agreed with the experimental data and was found to be considerably smaller than that for the E rotamer. The relative energies of the four ions that could be formed by adding a proton to methyl acetate were related to the orientation of the dipole components at oxygen. The methyl cation affinities of the methyl acetate conformers were found to parallel the proton affinities and gave the same preferred direction of addition. The proton affinity of valerolactone was calculated to be greater than that for butyrolactone in good accord with the experimental results.