1-acetoxy-2-fluoro-1-phenylethane | 130409-86-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-acetoxy-2-fluoro-1-phenylethane
• 英文别名: 2-fluoro-1-phenylethyl acetate；1-phenyl-2-fluoroethylacetate；(2-fluoro-1-phenylethyl) acetate
• CAS: 130409-86-8
• 化学式: C₁₀H₁₁FO₂
• 分子量: 182.195
• InChiKey: KTOVQUARGMSOKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetoxy-2-fluoro-1-phenylethane 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以57%的产率得到1-(4-氟苯基)乙醇
  参考文献：
  名称：

  A Unique Chelating Effect of Sc(OTf)₃to Organofluorine Compounds

  摘要：

  在三氟甲磺酸钪的催化下，位于 β 位置的含有两个或三个氟原子的乙酸酯裂解为乙酰氧基的过程异常迅速。水解的高效率是由于钪与氟原子和醋酸基的螯合作用。

  DOI：

  10.1246/cl.1999.459
• 作为产物：
  描述：

  phenylmagnesium bromide 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 1-acetoxy-2-fluoro-1-phenylethane
  参考文献：
  名称：

  带有一氟甲基的旋光性结构单元的合成

  摘要：

  已经进行了通过相应的乙酸酯的微生物水解制备的具有一氟甲基的旋光分子的合成工具的研究。确定这些单氟甲基化的手性化合物的绝对构型。

  DOI：

  10.1016/s0022-1139(00)81995-8

文献信息

• Power- and structure-variable fluorinating agents. The N-fluoropyridinium salt system
  作者：Teruo Umemoto、Shinji Fukami、Ginjiro Tomizawa、Kikuko Harasawa、Kosuke Kawada、Kyoichi Tomita

  DOI：10.1021/ja00179a047

  日期：1990.11

  N-Fluoropyridinium salts provide a new system of fluorinating agents by which a wide range of nucleophilic substrates differing in reactivity can be fluorinated due to the varying degree of fluorinating power and also fluorinated very selectively through structural alteration. The scope of selective fluorination should be broadened considerably on the basis of the present results. The N-fluoropyridinium

  N-氟吡啶鎓盐提供了一种新的氟化剂系统，通过该系统，由于氟化能力的不同程度，反应性不同的各种亲核底物可以被氟化，并且还可以通过结构改变非常有选择性地氟化。在现有结果的基础上，选择性氟化的范围应该大大拓宽。因此，N-氟吡啶鎓盐系统应该可以制备许多有用的有机氟化合物
• Synthesis and characterization of a novel N–F reagent derived from the ethano-Tröger's base: ¹J_FN coupling constants as a signature for the N–F bond
  作者：Raul Pereira、Jamie Wolstenhulme、Graham Sandford、Timothy D. W. Claridge、Véronique Gouverneur、Ján Cvengroš

  DOI：10.1039/c5cc08375c

  日期：——

  Methylation followed by fluorination of the ethano-Tröger's base affords a novel N–F reagent more reactive than Selectfluor bis(tetrafluoroborate). This study provides ¹J_FN coupling constants to characterize the N–F group.

  对乙烯-特罗杰碱进行甲基化和氟化，得到一种比Selectfluor bis(tetrafluoroborate)更具反应性的新型N-F试剂。该研究提供了¹J_FN耦合常数以表征N-F基团。
• Highly Selective Fluorinating Agents: a Counteranion-Bound N-Fluoropyridinium Salt System
  作者：Teruo Umemoto、Ginjiro Tomizawa

  DOI：10.1021/jo00125a049

  日期：1995.10

  A series of alkyl- or (trifluoromethyl)-substituted N-fluoropyridinium-2-sulfonates 2a-h, differing in fluorinating power, were synthesized, and assessment was made of the effectiveness of each selective fluorinating agent. N-Fluoropyridinium-3- and -4-sulfonates 3 and 4 were also synthesized. Power-variables 2a-h were found to be highly selective fluorinating agents for a wide range of nucleophilic substrates such as activated aromatics, enol trialkylsilyl and alkyl ethers, active methylene compounds, activated olefins, and sulfides. Thus, phenol, naphthol, phenylurethane, and the trimethylsilyl ether of phenol were exclusively or highly selectively fluorinated at the o-position with 2f-h. Conjugated enol trialkylsilyl ethers of a steroid were regioselectively fluorinated at the 6-position with moderately powerful 2b-e. This regioselectivity increased with the bulkiness of the silyl part, and with the most bulky triisopropylsilyl group exclusive B-fluorination was achieved. Preferential beta-stereoselective fluorination at the 6-position was observed. N-Fluoropyridinium-2-sulfonates were activated with an acid. This acid-catalyzed fluorination led to the preferential p-fluorination of anisole. The present results can be explained based on the capacity of the 2-sulfonate anion to interact with the hydroxy group of phenol or naphthol, NH group of phenylurethane, silicon atoms of silyl ethers, or protons of acids.
• N-Fluorobis[(perfluoroalkyl)sulfonyl]imides: reactions with some olefins via .alpha.-fluoro carbocationic intermediates
  作者：Darryl D. DesMarteau、Ze Qi Xu、Michael Witz

  DOI：10.1021/jo00028a042

  日期：1992.1

  N-Fluorobis(perfluoroalkyl)sulfonyl]imides are a new class of electrophilic fluorinating agents. Reaction of (CF3SO2)2NF (1) with olefins gave various products, depending on the reaction conditions and the structure of the substrate. In solvents of higher nucleophilicity such as H2O, acetic acid, aqueous HCl, and (HF)(n)Py, alpha-fluorohydrins or their acetates, alpha,beta-chlorofluoro- and alpha,beta-difluoroalkanes were obtained. In acetic acid, trans-stilbene and tetraphenylethylene produced the rearranged, nonfluorinated aldehyde and ketone. Evidence is presented for the reactions proceeding via a one-electron transfer mechanism involving alpha-fluorocarbocationic intermediates.
• N-FLUOROPYRIDINIUM TRIFLATE: AN ELECTROPHILIC FLUORINATING AGENT
  作者：Umemoto, Teruo、Tomita, Kyoichi、Kawada, Kosuke

  DOI：10.15227/orgsyn.069.0129

  日期：——