2-ethylhexyl triflate | 1338823-88-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2-ethylhexyl triflate
• 英文别名: 2-Ethylhexyl trifluoromethanesulfonate；2-ethylhexyl trifluoromethanesulfonate
• CAS: 1338823-88-3
• 化学式: C₉H₁₇F₃O₃S
• 分子量: 262.293
• InChiKey: MDLKDRJDKJCDNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• 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：

  2-ethylhexyl triflate 在 sodium azide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.58h， 生成 iso-octyl azide
  参考文献：
  名称：

  Simple and Efficient Method for the Synthesis of Azides in Water-THF Solvent System

  摘要：

  DOI：

  10.1080/00304948.2011.594002
• 作为产物：
  描述：

  2-乙基己醇 、 三氟甲磺酸酐 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到2-ethylhexyl triflate
  参考文献：
  名称：

  Ultra-High-Response, Multiply Twisted Electro-optic Chromophores: Influence of π-System Elongation and Interplanar Torsion on Hyperpolarizability

  摘要：

  The systematic synthesis, structural, optical spectroscopic, and second-order nonlinear optical (NLO) characterization of a series of donor-acceptor poly-arylene chromophores which have heretofore unachieved pi-extension and substantial twisting from planarity, are reported: specifically, two-ring 2TTMC, dicyano (4-(3,5-dimethyl-1-(2-propylheptyl)-pyridin-1-ium-4-yl)-3-methylphenyl)methanide; three-ring 3TTMC, dicyano (4'-(3,5-dimethyl-1-(2-propylheptyl)pyridin-1-ium-4-yl)-2,2',3',5',6'-pentamethyl[1,1'-biphenyl]-4-yl)methanide; and four-ring 4TTMC, dicyano (4 ''-(3,5-ciimethyl-1- (2-propylheptyl)-pyridin-1-ium-4-yl)-2,2',3 '',6,6'-pentamethyl[1,1':4',1 ''-terphenyl]-4-yl)methanide. Single-crystal X-ray diffraction, DFT-optimized geometries, and B3LYP/INDO-SOS analysis identify three key features underlying the very large NLO response: (1) For ring catenation of three or greater, sterically enforced pi-system twists are only essential near the chromophore donor and acceptor sites to ensure large NLO responses. (2) For synthetic efficiency, deletion of one ortho-methyl group from o,o',o '',o'"-tetramethylbiaryl junctures, only slightly relaxes the biaryl twist angle from 89.6 degrees to similar to 80 degrees. (3) Increased arylene catenation from two to three to four rings (2TTMC -> 3TTMC -> 4TTMC) greatly enhances NLO response, zwitterionic charge localization, and thus the ground-state dipole moment, consistent with the contracted antiparallel solid-state pi-pi stacking distances of 8.665 -> 7.883 -> 7.361 angstrom, respectively. This supports zwitterionic ground states in these chromophores as do significant optical spectroscopic solvatochromic shifts, with aryl-aryl twisting turning on significant intra-subfragment absorption. Computed molecular hyperpolarizabilities (mu beta) approach an unprecedented 900 000 X 10(-48) esu, while estimated chromophore figures of merit, mu beta(vec)/M-w, approach 1500 X 10(-48) esu, 1.5 times larger than the highest known values for twisted chromophores and >33 times larger than that of planar donor-acceptor chromophores.

  DOI：

  10.1021/jacs.5b04636

文献信息

• US2022/389306
  申请人：——

  公开号：——

  公开（公告）日：——