(E)-1,4-diphenyl-3-fluoro-3-buten-1-yne | 130490-10-7

• 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: (E)-1,4-diphenyl-3-fluoro-3-buten-1-yne
• 英文别名: [(E)-2-fluoro-4-phenylbut-1-en-3-ynyl]benzene
• CAS: 130490-10-7
• 化学式: C₁₆H₁₁F
• 分子量: 222.262
• InChiKey: YJZKNWDUXWBCHH-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3-dibromo-2-fluoro-3-phenylpropanoic acid 在 palladium diacetate 、 碳酸氢钠 、 正丁胺 、 三苯基膦 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成 (E)-1,4-diphenyl-3-fluoro-3-buten-1-yne
  参考文献：
  名称：

  Eddarir, Said; Francesch, Charlette; Mestdagh, Helene, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 8-9, p. 741 - 756

  摘要：

  DOI：

文献信息

• A kinetic separation method for the stereoselective preparation of (Z)- and (E)-monofluoroenynes from E/Z mixtures of 1-bromo-1-fluoroolefins
  作者：Xin Zhang、Donald J. Burton

  DOI：10.1016/s0022-1139(01)00529-2

  日期：2001.12

  under similar conditions and longer reaction times (48 h) to give pure (E)-monofluoroenynes in excellent yields (78–89%). Thus, E/Z mixtures of 1-bromo-1-fluoroolefins could be kinetically separated into (Z)- and (E)-monofluoroenynes. This methodology provides a simple one-step unequivocal route to the isomerically pure (Z)- and (E)-monofluoroenynes from the readily available 1-bromo-1-fluoroolefins.

  1-溴-1-氟烯烃与1-炔烃的E / Z混合物与催化的Pd（PPh 3）2 Cl 2和CuI在室温下在三乙胺中的反应（16-24小时后）主要是（Z）-单氟炔（Z / E > 92/8），收率良好。通常可以通过色谱分离粗制的Z / E混合物来获得纯的（Z）-单氟炔。可以回收纯的（Z）-1-溴-1-氟烯烃，并在相似的条件下和更长的反应时间（48 h）下与1-炔烃反应，得到纯的（E）-一氟代炔类化合物，收率极高（78-89％）。因此，可以将1-溴-1-氟烯烃的E / Z混合物动力学分离为（Z）-和（E）-单氟炔烃。该方法学提供了一种简单的一步一步明确路线，从容易获得的1-溴-1-氟烯烃中获得异构纯的（Z）-和（E）-单氟炔烃。
• New methods for the synthesis of fluoroolefins via the palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes and organostannanes
  作者：Chen Chen、Keith Wilcoxen、Charles Q Huang、Nathalie Strack、James R McCarthy

  DOI：10.1016/s0022-1139(99)00172-4

  日期：2000.2

  The palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes and organostannanes provide two new facile methods to 1-substituted 1-fluoroolefins. The reactions proceed with retention of configuration in good to excellent yields.

  1-氟乙烯基卤化物与有机硼烷和有机锡的钯催化的交叉偶联反应为1-取代的1-氟烯烃提供了两种新的简便方法。反应以良好至优异的产率保持构型进行。
• Au(I) Fluorido Phosphine Complexes: Tools for the Hydrofluorination of Alkynes
  作者：Simon G. Rachor、Ruben Jaeger、Thomas Braun

  DOI：10.1002/ejic.202200158

  日期：2022.6.17

  Au(I) fluorido SPhos complexes react with alkynes to yield metal-fluorovinyl species. Addition of HCl resulted in protodeauration with retained stereoselectivity. Various Au(I) complexes were then compared in their ability to catalyze hydrofluorination reactions of 1-phenyl-1-propyne employing Et3N ⋅ 3HF as HF source.

  Au(I) fluorido SPhos 配合物与炔烃反应生成金属-氟乙烯基物质。添加 HCl 导致原型脱氧并保留立体选择性。然后比较了各种 Au(I) 配合物在使用 Et 3 N·3HF 作为 HF 源时催化 1-苯基-1-丙炔氢氟化反应的能力。
• Synthesis of fluorinated enynes via 1-bromo 1-fluoro alkenes
  作者：Said Eddarir、Charlette Francesch、Hélène Mestdagh、Christian Rolando

  DOI：10.1016/s0040-4039(00)97645-7

  日期：1990.1
• Synthesis of α-fluoro-β, γ-alkenylphosphonates and conjugated fluoroenynes from a common intermediate (α-fluoropropargyl) phosphonate
  作者：Farid Benayoud、Ling Chen、George A. Moniz、Antonio J. Zapata、Gerald B. Hammond

  DOI：10.1016/s0040-4020(98)01017-5

  日期：1998.12

  The efficient preparation of alpha-fluoro-beta,gamma-alkenylphosphonate 3, via catalytic hydrogenation of (alpha-fluoropropargyl)phosphonate ester 1, is described. Conjugated fluoroenynes 4 have been synthesized using a modified Horner Wadsworth Emmons (HWE) olefination of aldehydes or ketones and 1 in relatively good yields. Yields were lowered because of the formation of alpha-fluoro-gamma-hydroxyallenylphosphonate 5 during the reaction. The nature of the counterion was very important in the outcome of the HWE reaction; better yields of fluoroenynes were obtained when a potassium base was used instead of a lithium base. (C) 1998 Elsevier Science Ltd. All rights reserved.