2-(p-tolyl)-2,5-dihydrofuran | 188643-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(p-tolyl)-2,5-dihydrofuran
• 英文别名: 2-(4-methylphenyl)-2,5-dihydrofuran
• CAS: 188643-51-8
• 化学式: C₁₁H₁₂O
• 分子量: 160.216
• InChiKey: PPZZFMZROCNEKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(p-tolyl)buta-2,3-dien-1-ol 在 Ag⁽¹⁺⁾*C₄₄H₂₈O₄P^(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (R)-1-(p-tolyl)buta-2,3-dien-1-ol 、 2-(p-tolyl)-2,5-dihydrofuran
  参考文献：
  名称：

  Chiral Silver Phosphate-Catalyzed Cycloisomeric Kinetic Resolution of α-Allenic Alcohols

  摘要：

  A kinetic resolution of a-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.

  DOI：

  10.1021/ja300453u

文献信息

• Palladacycle-Catalyzed Regioselective Heck Reaction Using Diaryliodonium Triflates and Aryl Iodides
  作者：Lu Lei、Pei-Sen Zou、Zhi-Xin Wang、Cui Liang、Cheng Hou、Dong-Liang Mo

  DOI：10.1021/acs.orglett.1c04120

  日期：2022.1.21

  P-containing palladacycle-catalyzed regioselective Heck reaction of 2,3-dihydrofuran with diaryliodonium salts and aryl iodides to afford 2-aryl-2,5-dihydrofurans and 2-aryl-2,3-dihydrofurans, respectively, in good yields. Mechanistic studies revealed that the oxidative addition of diaryliodonium salts to palladacycles to form Pd(IV) species showed high chemoselectivity and that electron-rich aryl moieties

  我们描述了含 P 钯环催化的 2,3-二氢呋喃与二芳基碘鎓盐和芳基碘化物的区域选择性 Heck 反应，分别得到 2-aryl-2,5-dihydrofurans 和 2-aryl-2,3-dihydrofurans，在良好的产量。机理研究表明，二芳基碘鎓盐氧化加成到钯环上形成 Pd(IV) 物种显示出高化学选择性，并且富电子芳基部分优先转移到 Heck 产物上。DFT 计算表明，决定区域选择性的步骤是还原消除反应，而不是 Pd(IV)-氢化物中间体的异构化和重新插入双键。
• [EN] SPIRO-1,1'-BIINDANE-7,7-BISPHOSPHINE OXIDES AS HIGHLY ACTIVE SUPPORTING LIGANDS FOR PALLADIUM-CATALYZED ASYMMETRIC HECK REACTION<br/>[FR] OXYDES DE SPIRO-1,1'-BIINDANE-7,7-BISPHOSPHINE COMME LIGANDS DE SUPPORT HAUTEMENT ACTIFS POUR UNE RÉACTION DE HECK ASYMÉTRIQUE CATALYSÉE PAR DU PALLADIUM
  申请人：UNIV NANYANG TECH

  公开号：WO2014196930A1

  公开（公告）日：2014-12-11

  The present invention relates to catalyst complexes comprising palladium (Pd) and at least one spiro-1,1 '-biindane-7,7'- bisphosphine oxide ligand as disclosed herein, and their use. The present invention is further directed to the asymmetric Pd-catalyzed covalent carbon-carbon single bond formation from aryl, heteroaryl and alkenyl triflates and halides and olefins utilising the said catalyst complexes.

  本发明涉及包含钯（Pd）和至少一种如本文所述的螺-1,1'-联萘-7,7'-双膦氧配体的催化剂复合物，以及它们的使用。本发明进一步涉及利用所述催化剂复合物从芳基、杂环芳基和烯基三氟甲烷磺酸酯和卤代物以及烯烃中进行不对称Pd催化的共价碳-碳单键形成。
• Palladium-Catalyzed Arylation and Vinylation of 2,3-Dihydrofuran with Hypervalent Iodonium Salts
  作者：Suk-Ku Kang、Tokutaro Yamaguchi、Jae-Sun Kim、Sang-Chul Choi、Chuljin Ahn

  DOI：10.1080/00397919708003056

  日期：1997.3

  Abstract The palladium-catalyzed arylation and vinylation of 2,3-dihydrofuran with aryl and alkenyl iodonium salts afforded 2-phenyl- or 2-alkenyl-2,5-dihydrofurans at room temperature in an aqueous medium.

  摘要 钯催化的 2,3-二氢呋喃与芳基和烯基碘鎓盐的芳基化和乙烯基化反应在室温下在水性介质中得到 2-苯基-或 2-烯基-2,5-二氢呋喃。
• SPIRO-1,1'-BINDANE-7,7-BISPHOSPHINE OXIDES AS HIGHLY ACTIVE SUPPORTING LIGANDS FOR PALADIUM-CATALYZED ASYMMETRIC HECK REACTION
  申请人：NANYANG TECHNOLOGICAL UNIVERSITY

  公开号：US20160136629A1

  公开（公告）日：2016-05-19

  The present invention relates to catalyst complexes comprising palladium (Pd) and at least one spiro-1,1′-biindane-7,7′-bisphosphine oxide ligand as disclosed herein, and their use. The present invention is further directed to the asymmetric catalyzed covalent carbon-carbon single bond formation from aryl, heteroaryl and alkenyl triflates and halides and olefins utilising the said catalyst complexes.

  本发明涉及包含钯（Pd）和至少一种螺-1,1'-联萘-7,7'-双膦氧配体的催化剂复合物，以及它们的用途。本发明还进一步涉及利用所述催化剂复合物不对称催化芳基、杂环基和烯基三氟甲烷基和卤代物以及烯烃之间的共价碳-碳单键形成。
• SPIRO-1,1'-BIINDANE-7,7-BISPHOSPHINE OXIDES AS HIGHLY ACTIVE SUPPORTING LIGANDS FOR PALLADIUM-CATALYZED ASYMMETRIC HECK REACTION
  申请人：Nanyang Technological University

  公开号：EP3004120B1

  公开（公告）日：2018-08-29