2,2-difluoro-1,4-diphenylbut-3-yn-1-ol | 110889-05-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2,2-difluoro-1,4-diphenylbut-3-yn-1-ol
• 英文别名: 2,2-Difluoro-1,4-diphenyl-3-butyn-1-ol
• CAS: 110889-05-9
• 化学式: C₁₆H₁₂F₂O
• 分子量: 258.267
• InChiKey: XGDWKWBZMJAVMM-UHFFFAOYSA-N

物化性质

• 沸点：
  386.2±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-1,4-diphenylbut-3-yn-1-ol 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到3,3-difluoro-2,5-diphenyl-2,3-dihydrofuran
  参考文献：
  名称：

  Au-catalyzed intramolecular hydroalkoxylation of gem-difluorinated alkynols

  摘要：

  The intramolecular hydroalkoxylation of gem-difluorinated alkynols was found possible under Au catalysis, allowing for the preparation of a series of fluorinated heterocycles. The nature of the solvent was found to be especially critical in the cyclization of gem-difluorohomopropargylic alcohols as it dictated whether the resulting 2,3-dihydrofuran underwent subsequent aromatization to the corresponding furan or not.

  DOI：

  10.1016/j.jfluchem.2018.09.009
• 作为产物：
  描述：

  DL-扁桃酸甲酯 在 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 4-甲基苯磺酸吡啶 、 二甲基亚砜 、 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 67.0h， 生成 2,2-difluoro-1,4-diphenylbut-3-yn-1-ol
  参考文献：
  名称：

  Au-catalyzed intramolecular hydroalkoxylation of gem-difluorinated alkynols

  摘要：

  The intramolecular hydroalkoxylation of gem-difluorinated alkynols was found possible under Au catalysis, allowing for the preparation of a series of fluorinated heterocycles. The nature of the solvent was found to be especially critical in the cyclization of gem-difluorohomopropargylic alcohols as it dictated whether the resulting 2,3-dihydrofuran underwent subsequent aromatization to the corresponding furan or not.

  DOI：

  10.1016/j.jfluchem.2018.09.009

文献信息

• Nucleophilic and electrophilic substitutions of difluoropropargyl bromides
  作者：Gerald B. Hammond

  DOI：10.1016/j.jfluchem.2005.12.024

  日期：2006.5

  electrophilically substituted difluoropropargyl derivatives via magnesium and fluoride promoted reactions. An indium-mediated reaction of silyldifluoropropargyl bromide, followed by electrophilic trapping with bromine led to a very useful bromoallene, which was then used in reactions with nucleophiles (C, O, N, P, S, Hal) to yield a de facto bimolecular nucleophilic substitution of a difluoropropargyl

  当进行取代的碳原子键合到两个氟原子上时，很少在氟化的炔丙基或烯丙基模块上研究基本的有机反应，如亲核取代和亲电子取代。在本文中，我们报道了使用多种烷基，芳基或甲硅烷基底物从取代的乙炔和二溴二氟甲烷实际合成二氟炔丙基溴的方法。O-，S的合成还描述了二氟炔丙基溴的-和羧酸衍生物。这些化合物是通过镁和氟化物促进的反应合成亲电子取代的二氟炔丙基衍生物的合适原料。甲硅烷基二氟炔丙基溴的铟介导反应，然后用溴进行亲电捕获，生成了非常有用的溴丙二烯，然后将其用于与亲核试剂（C，O，N，P，S，Hal）反应，生成事实上的双分子亲核试剂二氟炔丙基溴的取代。
• Synthesis of 3-Fluoro-2,5-Disubstituted Furans and Further Derivative Reactions to Access Fluorine-Containing 3,3′-Bifurans and Tetrasubstituted Furans
  作者：Gang Zhao、Shi-Zheng Zhu、Peng Li、Zhuo Chai

  DOI：10.1055/s-2008-1078053

  日期：——

  2,5-Disubstituted 3-fluorofurans were synthesized in 42-99% yield via DBU-promoted cyclization reactions of electron-deficient gem-difluorohomopropargyl alcohols. Starting from these compounds, a series of fluorinated 3,3′-bifurans and tetrasubstituted furans were also prepared through a fluorine-directed ortho-functionalization process.

  合成了2,5-二取代的3-氟呋喃，产率为42-99%，通过DBU促进的电子缺乏型gem-二氟同炔醇的环化反应。从这些化合物出发，还通过氟引导的邻位功能化过程制备了一系列氟化的3,3′-双呋喃和四取代呋喃。
• A new and concise synthesis of 3-fluoro-2,5-disubstituted furans
  作者：Hing L. Sham、David A. Betebenner

  DOI：10.1039/c39910001134

  日期：——

  A highly efficient synthesis of a series of 3-fluoro-2,5-disubstituted furans by a two-step sequence is described.

  描述了一种通过两步序列高效合成一系列3-氟-2,5-二取代呋喃的方法。
• The Reformatsky reaction of bromodifluoromethylacetylene derivatives: Application to the synthesis of fluorinated bioactive compounds
  作者：Yuji Hanzawa、Kazuhiko Inazawa、Akira Kon、Hironobu Aoki、Yoshiro Kobayashi

  DOI：10.1016/s0040-4039(00)95806-4

  日期：1987.1

  The Reformatsky reaction of bromodifluoromethylacetylene derivatives with aldehydes gave fluorinated homopropargylic alcohols. The adducts obtained from D-glyceraldehyde acetonide were converted to 2,2-difluoro-2-deoxy-D-ribose and intermediates to fluorinated arachidonic acid and its metabolite.

  溴二氟甲基乙炔衍生物与醛的Reformatsky反应得到氟化的均丙醇。由D-甘油醛丙酮化物获得的加合物被转化为2，2-二氟-2-脱氧-D-核糖，中间体被转化为氟化花生四烯酸及其代谢产物。
• Indium-Mediated Reaction of 3-Bromo-3,3-difluoropropene and Bromodifluoromethylacetylene Derivatives with Aldehydes
  作者：Masayuki Kirihara、Tomofumi Takuwa、Shinobu Takizawa、Takefumi Momose、Hideo Nemoto

  DOI：10.1016/s0040-4020(00)00749-3

  日期：2000.10

  Aldehydes reacted with 3-bromo-3,3-difluoropropene at the a-position in the presence of indium to afford 1-substituted-2,2-difluorobut-3-en-1-ols. Ketones and other electrophiles are inert under the examined conditions. The reaction of bromodifluoromethyl-acetylene derivatives with an aldehyde in the presence of indium provided difluorohomopropargylic alcohols. These reactions efficiently proceeded in polar solvents (water, DMF) under mild conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.