3-tridecafluorohexylcoumarin | 132605-39-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-tridecafluorohexylcoumarin
• 英文别名: 3-(perfluorohexyl)-2H-chromen-2-one；3-(1,1,2,2,3,3,4,4,5,5,6,6,6-Tridecafluorohexyl)chromen-2-one
• CAS: 132605-39-1
• 化学式: C₁₅H₅F₁₃O₂
• 分子量: 464.183
• InChiKey: ZZCNFYFYXHWPTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  香豆素 以63%的产率得到
  参考文献：
  名称：

  Bing-Nan Huang, Jin-Tao Liu, Wei-Yuan Huang, J. Chem. Soc. Perkin Trans. 1, (1994) N 1, S 101- 104

  摘要：

  DOI：

文献信息

• Direct perfluoroalkylation of coumarins by perfluoroalkyl iodides in the presence of sodium hydroxymethanesulphinate (Rongalite)
  作者：Bingnan Huang、Jintao Liu、Weiyuan Huang

  DOI：10.1039/c39900001781

  日期：——

  C(3) substituted perfluoroalkylcoumarins are prepared readily by the reaction of coumarins with perfluoroalkyl iodides in the presence of sodium hydroxymethanesulphinate (Rongalite).

  C(3)取代的全氟烷基香豆素通过在氢氧基甲基亚磺酸钠（Rongalite）存在下，将香豆素与全氟烷基碘化物反应而制备。
• Fe and Ni-catalyzed electrochemical perfluoroalkylation of C—H bonds of coumarins
  作者：M. N. Khrizanforov、S. O. Strekalova、V. V. Grinenko、V. V. Khrizanforova、T. V. Gryaznova、Yu. H. Budnikova

  DOI：10.1007/s11172-017-1906-5

  日期：2017.8

  A new method for the preparation of perfluoroalkylcoumarins in a single step is developed. The compounds are prepared via electrocatalytic reduction of a 1 : 1 mixture of an aromatic compound (coumarin, 6-methylcoumarin, and 7-methylcoumarin) and a fluoroalkylating reagent under mild conditions (room temperature, normal pressure) using [bipyFeII] or [bipyNiII] complexes as catalysts. The developed

  开发了一种单步制备全氟烷基香豆素的新方法。这些化合物是通过使用 [bipyFeII] 或 [bipyNiII] 在温和条件（室温、常压）下电催化还原芳香族化合物（香豆素、6-甲基香豆素和 7-甲基香豆素）和氟烷基化试剂的 1:1 混合物制备的] 络合物作为催化剂。所开发的方法能够以高产率和 100% 的氟烷基化试剂转化率获得全氟烷基香豆素。
• Huang, Bing-Nan; Liu, Jin-Tao; Huang, Wei-Yuan, Journal of the Chemical Society. Perkin transactions I, 1994, # 1, p. 101 - 104
  作者：Huang, Bing-Nan、Liu, Jin-Tao、Huang, Wei-Yuan

  DOI：——

  日期：——
• Visible-Light-Driven, Photoredox-Catalyzed Cascade of <i>ortho-</i>Hydroxycinnamic Esters To Access 3-Fluoroalkylated Coumarins
  作者：Dan Song、Chao-Ming Wang、Zhi-Peng Ye、Peng-Ju Xia、Zhi-Xiong Deng、Jun-An Xiao、Hao-Yue Xiang、Hua Yang

  DOI：10.1021/acs.joc.9b00715

  日期：2019.6.7

  A general and straightforward protocol for di-/perfluoroalkylation of ortho-hydroxycinnamic esters via a photoredox-catalyzed cascade was developed to access a variety of 3-fluoroalkylated coumarins. This method was characterized by all-in-one synthetic design, simplified operation, mild reaction conditions, and broad substrate scope. Moreover, a sequential one-pot procedure starting from commercially available salicylaldehyde was also successfully realized to synthesize 3-fluoroalkylated coumarins.
• The reaction of sodium perfluoroalkanesufinates with coumarin
  作者：Jin-Tao Liu、Wei-Yuan Huang

  DOI：10.1016/s0022-1139(99)00008-1

  日期：1999.6

  The reaction of sodium perfluoroalkanesufinates with coumarin in the presence of Mn(OAc)(3). 2H(2)O was studied. Sodium perfluoroalkanesufinates, RFSO2Na [R-F=F(CF2)(6), 2a; F(CF2)(7), 2b; F(CF2)(8), 2c; Cl(CF2)(4), 2d; Cl(CF2)(6), 2e],reacted readily with a small excess of coumarin to give the corresponding 3-perfluoroalkylated coumarins (3a-e), while poly-perfluoroalkylation of coumarin occurred when excess 2 was used in the reaction, and 3,6-diperfluoroalkylcoumarins (4) and 3,6,8-triperfluoroalkylcoumarins (5) were isolated as major products according to the ratio of starting materials. (C) 1999 Elsevier Science S.A. All rights reserved.