trans-2-fluoro-1-methoxyindane | 82936-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: trans-2-fluoro-1-methoxyindane
• 英文别名: trans-1-Fluoro-2-methoxyindan
• CAS: 82936-93-4
• 化学式: C₁₀H₁₁FO
• 分子量: 166.195
• InChiKey: GAKLZAKJYBSETP-UWVGGRQHSA-N

物化性质

• 沸点：
  215.8±40.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  甲醇 、 茚 在 乙酰基次氟酸酯 、 mercury(II) diacetate 作用下， 生成 trans-2-fluoro-1-methoxyindane
  参考文献：
  名称：

  Synthesis of fluoro ethers with acetyl hypofluorite

  摘要：

  DOI：

  10.1021/jo00388a046

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。
• Evidence for the existence of methyl hypofluorite: methanolysis of xenon difluoride
  作者：Dale F. Shellhamer、Carol M. Curtis、Don R. Hollingsworth、Mark L. Ragains、Ruthann E. Richardson、Victor L. Heasley、Gene E. Heasley

  DOI：10.1016/s0040-4039(00)87287-1

  日期：——

  Methyl hypofluorite is indicated as an intermediate in the reaction of xenon difluoride with alkenes in methanol as solvent.

  次氟甲烷指示为在甲醇作为溶剂的二氟化氙与烯烃反应中的中间体。
• Regioselective chemistry of methoxyxenon fluoride
  作者：Dale F. Shellhamer、Carl M. Curtis、Robert H. Dunham、Don R. Hollingsworth、Mark L. Ragains、Ruthann E. Richardson、Victor L. Heasley、Scott A. Shackelford、Gene E. Heasley

  DOI：10.1021/jo00215a032

  日期：1985.7
• The Chemistry of Methyl Hypofluorite: Its Reactions with Various Unsaturated Centers
  作者：Shlomo Rozen、Eyal Mishani、Moshe Kol、Iris Ben-David

  DOI：10.1021/jo00094a047

  日期：1994.7

  Methyl hypofluorite was until recently grouped as a hypothetical member of those smallest organic molecules which had not been synthesized. Passing F-2 through a solution of methanol in MeCN or PrCN resulted in its successful preparation. MeOF is an unique reagent, since it generates the novel electrophilic methoxylium moiety in contrast to the much more common methoxide group. This hypofluorite was reacted with several types of olefins including benzylic, cyclic, bicyclic, straight chain, and steroidal ones. In most cases the regioselectivity is very good, reflecting the unique polarization of the reagent: MeO(delta+)F(delta-). The stereoselectivity tends to be less emphasized, but usually anti addition is dominant.
• Shellhamer, Dale F.; Carter, Steven L.; Dunham, Robert H., Journal of the Chemical Society. Perkin transactions II, 1989, p. 159 - 166
  作者：Shellhamer, Dale F.、Carter, Steven L.、Dunham, Robert H.、Graham, Stuart N.、Spitsbergen, Mark P.、et al.

  DOI：——

  日期：——