1-(4-(2,3-dihydrofuran-2-yl)phenyl)ethanone | 131516-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(2,3-dihydrofuran-2-yl)phenyl)ethanone
• 英文别名: 2-(4-acetylphenyl)-2,3-dihydrofuran；2-(4-acetophenyl)-2,3-dihydrofuran；1-[4-(2,3-Dihydrofuran-2-yl)phenyl]ethanone
• CAS: 131516-06-8
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: CPDVZKGTHRAREL-UHFFFAOYSA-N

物化性质

• 沸点：
  316.5±42.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氢呋喃 、 对氯苯乙酮 在 tris(dibenzylideneacetone)dipalladium (0) 、 三叔丁基膦 、 Cy₂NMe₂ 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以68%的产率得到1-(4-(2,3-dihydrofuran-2-yl)phenyl)ethanone
  参考文献：
  名称：

  在温和条件下用于芳基氯化物和芳基溴化物的 Heck 反应的多功能催化剂

  摘要：

  在 Cy2NMe 存在下，Pd/P(t-Bu)3 可作为一种非常温和且用途广泛的催化剂，用于芳基氯化物和溴化物的 Heck 反应。空间和电子上不同的芳基溴化物阵列以及活化的芳基氯化物，在室温下与一系列单取代和双取代的烯烃偶联，为芳基化产物提供高 E/Z 立体选择。广泛的电子中性和富电子芳基氯化物的相应反应在升高的温度下进行，并且具有高选择性。在范围和温和性方面，Pd/P(t-Bu)3/Cy2NMe 代表了先前报道的这些 Heck 偶联过程的催化剂的进步。

  DOI：

  10.1021/ja010988c

文献信息

• Oxime-Derived Palladium Complexes as Very Efficient Catalysts for the Heck–Mizoroki Reaction
  作者：Diego A. Alonso、Carmen Nájera、Ma Carmen Pacheco

  DOI：10.1002/1615-4169(200202)344:2<172::aid-adsc172>3.0.co;2-9

  日期：2002.2

  Oxime-derived, chloro-bridged palladacycles 16 are efficient complexes for the Heck vinylation of aryl halides. The isolated catalysts are thermally stable, not sensitive to air or moisture and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions, with aryl iodides, bromides and chlorides with acrylic esters and olefins displaying turnover numbers (TON) of up to 10(10) for phenyl iodide and turnover frequencies (TOF) of 1.4 x 10(8) h(-1). Deactivated aryl bromides undergo the Heck reaction with styrene with TON and TOF values up to 97,000 and 6063 h-1, respectively. Even aryl chlorides undergo the coupling reaction with olefins with TON up to 920. Complexes 16 catalyze the synthesis of 2,3-disubstituted indenones and indoles in good yields via annulation reaction of internal alkynes with o-bromo- or o-chlorobenzaldehyde and o-iodoaniline, respectively.
• Controlling Olefin Isomerization in the Heck Reaction with Neopentyl Phosphine Ligands
  作者：Matthew G. Lauer、Mallory K. Thompson、Kevin H. Shaughnessy

  DOI：10.1021/jo501840u

  日期：2014.11.21

  The use of neopentyl phosphine ligands was examined in the coupling of aryl bromides with alkenes. Di-tert-butylneopentylphosphine (DTBNpP) was found to promote Heck couplings with aryl bromides at ambient temperature. In the Heck coupling of cyclic alkenes, the degree of alkene isomerization was found to be controlled by the choice of ligand with DTBNpP promoting isomerization to a much greater extent than trineopentylphosphine (TNpP). Under optimal conditions, DTBNpP provides high selectivity for 2-aryl-2,3-dihydrofuran in the arylation of 2,3-dihydrofuran, whereas TNpP provided high selectivity for the isomeric 2-aryl-2,5-dihydrofuran. A similar complementary product selectivity is seen in the Heck coupling of cyclopentene. Heck coupling of 2-bromophenols or 2-bromoanilides with 2,3-dihydrofurans affords 2,5-epoxybenzoxepin and 2,5-epoxybenzazepins, respectively.
• [Pd/Base/QX] catalyst systems for directing Heck-type reactions
  作者：Tuyet Jeffery、Marc David

  DOI：10.1016/s0040-4039(98)01135-6

  日期：1998.8

  Palladium-catalyzed arylation of 2,3-dihydrofuran can be directed at will by an appropriate selection of the [Pd/Base/QX] catalyst systems, (C) 1998 Elsevier Science Ltd. All rights reserved.
• A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions
  作者：Adam F. Littke、Gregory C. Fu

  DOI：10.1021/ja010988c

  日期：2001.7.1

  for Heck reactions of aryl chlorides and bromides. A sterically and electronically diverse array of aryl bromides, as well as activated aryl chlorides, couple with a range of mono- and disubstituted olefins at room temperature, furnishing the arylated product with high E/Z stereoselection. The corresponding reactions of a broad spectrum of electron-neutral and electron-rich aryl chlorides proceed at

  在 Cy2NMe 存在下，Pd/P(t-Bu)3 可作为一种非常温和且用途广泛的催化剂，用于芳基氯化物和溴化物的 Heck 反应。空间和电子上不同的芳基溴化物阵列以及活化的芳基氯化物，在室温下与一系列单取代和双取代的烯烃偶联，为芳基化产物提供高 E/Z 立体选择。广泛的电子中性和富电子芳基氯化物的相应反应在升高的温度下进行，并且具有高选择性。在范围和温和性方面，Pd/P(t-Bu)3/Cy2NMe 代表了先前报道的这些 Heck 偶联过程的催化剂的进步。