1-fluoro-2-methoxy-1,2-diphenylethane | 156479-56-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-fluoro-2-methoxy-1,2-diphenylethane
• 英文别名: 1,2-diphenyl-2-fluoro-1-methoxyethane；(1-fluoro-2-methoxy-2-phenylethyl)benzene
• CAS: 156479-56-0
• 化学式: C₁₅H₁₅FO
• 分子量: 230.282
• InChiKey: BSWPIIIKHQFYGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 反式-1,2-二苯乙烯 在 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 1-fluoro-2-methoxy-1,2-diphenylethane
  参考文献：
  名称：

  A mild, selective method for preparation of vicinal fluoro ethers using “F-Teda-BF4”

  摘要：

  Vicinal alkoxy fluorides are efficiently formed by room temperature reaction of phenyl substituted alkenes with commercially available 1-chloromethyl-4-fluoro-1,4-diazobicyclo[2.2.2]octane bis tetrafluoroborate (Selectfluor(TM) F-Teda BF4) in CH3CN in the presence of various alcohols. The reaction follows Markovnikov-type regioselectivity, while stereoselectivity in the case of phenyl substituted benzocyclenes strongly depends on the ring size and the structure of the alcohol.

  DOI：

  10.1016/s0040-4039(00)79977-1

文献信息

• Stereochemistry and Some Kinetic Aspects of Fluorination of Phenyl-Substituted Alkenes with Selectfluor^TMReagent F-TEDA-BF₄
  作者：Stojan Stavber、Tjaša Sotler-Pecan、Marko Zupan

  DOI：10.1246/bcsj.69.169

  日期：1996.1

  while equal amounts of both diastereoisomers were formed in the case of (E)-1-phenyl-1-propene and acenaphthylene. In the phenyl-substituted benzocyclene series the stereochemistry of fluoro-alkoxylation was found to be dependent on ring size and on the structure of the alcohol. The resulting vicinal fluoroalkoxy adducts were transformed by heating in aqueous HBr to 2-fluoro-1-phenylbenzocyclenes. Correlation

  在各种醇存在下，苯基取代的烯烃与 SelectfluorTM 氟化试剂 F-TEDA-BF4 的反应导致形成具有 Markovnikov 类型区域选择性的邻位氟烷氧基加合物。发现氟甲氧基加成反应的立体化学在 (Z)-茋、茚和二苯并丁二烯酮的情况下略占优势，而在 (E)-1-苯基的情况下形成等量的两种非对映异构体-1-丙烯和苊。在苯基取代的苯并环烯系列中，发现氟烷氧基化的立体化学取决于环的大小和醇的结构。所得的邻位氟烷氧基加合物通过在 HBr 水溶液中加热转化为 2-氟-1-苯基苯并环烯。
• Isolation and characterization of methyl hypofluorite (CH3OF)
  作者：Moshe Kol、Shlomo Rozen、Evan Appelman

  DOI：10.1021/ja00007a043

  日期：1991.3

  Methyl hypofluorite (CH 3 OF) has been prepared by the reaction of elemental fluorine with methanol in acetonitrile or propionitrile at low temperature. It was removed from the reaction mixture in a stream of nitrogen and purified by fractional distillation. The compound is moderately long-lived, although the liquid has exploded upon rapid warming. The liquid compound has a freezing point of about

  次氟酸甲酯 (CH 3 OF) 是通过元素氟与甲醇在乙腈或丙腈中在低温下反应制备的。在氮气流中将其从反应混合物中除去并通过分馏纯化。该化合物的寿命适中，尽管这种液体在快速升温时会发生爆炸。液体化合物的凝固点约为 -142°C，蒸气压测量表明正常沸点为 -32.6±0.9°C，蒸发焓为 23.37±0.26 kJ/mol。蒸气的红外光谱与分子与 CH 3 OH 和 CF 3 OF 同构。该化合物还通过质谱和 1 H、 19 F 和 13 C NMR 光谱进行了表征。
• Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts (selectfluor reagents)
  作者：G. Sankar Lal

  DOI：10.1021/jo00062a023

  日期：1993.5

  The new ''N-F''-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts8d (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclo[2.2.2]octane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates. These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing alpha-H atoms, certain carbanions, and mildly activated aromatic compounds. The products were obtained with good yields and regioselectivity under very mild reaction conditions.
• Synthesis of fluoro ethers with acetyl hypofluorite
  作者：David Hebel、Shlomo Rozen

  DOI：10.1021/jo00388a046

  日期：1987.6
• KOL, MOSHE;ROZEN, SHLOMO;APPELMAN, EVAN, J. AMER. CHEM. SOC., 113,(1991) N, C. 2648-2651
  作者：KOL, MOSHE、ROZEN, SHLOMO、APPELMAN, EVAN

  DOI：——

  日期：——