(Z)-1,3-diphenyl-1-propen-2-yl tosylate | 849943-87-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-1,3-diphenyl-1-propen-2-yl tosylate
• 英文别名: (Z)-1,3-diphenylprop-1-en-2-yl 4-methylbenzenesulfonate；(Z)-1,3-diphenylpropen-2-yltosylate；[(Z)-1,3-diphenylprop-1-en-2-yl] 4-methylbenzenesulfonate
• CAS: 849943-87-9
• 化学式: C₂₂H₂₀O₃S
• 分子量: 364.465
• InChiKey: SRPABZNLNSHMMX-PGMHBOJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-1,3-diphenyl-1-propen-2-yl tosylate 、 甲基硼酸 在 potassium phosphate 、 2-(二环己基膦)3,6-二甲氧基-2′,4′,6′-三异丙基-1,1′-联苯 、 palladium diacetate 作用下， 以 2-甲基-2-丁醇 为溶剂， 以78%的产率得到(E)-(2-methylprop-1-ene-1,3-diyl)dibenzene
  参考文献：
  名称：

  A Versatile Catalyst System for Suzuki−Miyaura Cross-Coupling Reactions of C(sp²)-Tosylates and Mesylates

  摘要：

  A catalyst system for the Suzuki-Miyaura cross-coupling reactions of aryl and vinyl tosylates and mesylates has been developed. This catalyst displays excellent functional group tolerance and allows the coupling of heteroarylboronic acids with aryl tosylates and mesylates to be performed in high yields. Moreover, reactions employing alkylboronic acids, as well as heteroaryl, vinyl, and allylic pinacol boronate esters, were conducted with high efficiencies.

  DOI：

  10.1021/ol9015892
• 作为产物：
  描述：

  4-甲苯磺酸酐 、 二苄基甲酮 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 7.67h， 以83%的产率得到(Z)-1,3-diphenyl-1-propen-2-yl tosylate
  参考文献：
  名称：

  通过外部无CO钯催化烯基甲苯磺酸盐的羰基化反应制备α，β-不饱和酯和酰胺

  摘要：

  描述了甲酸酯与甲酸苯酯的钯催化羰基化。该程序既不需要外部一氧化碳，也不需要任何耐压设备。各种环状和无环烯基甲苯磺酸盐可以良好的产率转化为相应的苯基酯。此外，该方法对于α，β-不饱和酰胺的一锅法合成是有效的。

  DOI：

  10.1016/j.tetlet.2012.07.057

文献信息

• Nickel-Catalyzed Cyanation of Phenol Derivatives with Zn(CN)₂ Involving C–O Bond Cleavage
  作者：Yi Gan、Gaonan Wang、Xin Xie、Yuanhong Liu

  DOI：10.1021/acs.joc.8b02498

  日期：2018.11.16

  An efficient nickel-catalyzed cyanation of aryl sulfonates, fluorosulfonates, and sulfamates with Zn(CN)2 was developed, which provides a facile access to the nitrile products in generally good to excellent yields. The reaction is accomplished by using NiII complex as the precatalyst and DMAP as the additive. The method also displays wide functional group compatibility; for example, keto, methoxy,

  开发了一种有效的镍催化的芳基磺酸盐，氟磺酸盐和氨基磺酸盐与Zn（CN）2的氰化氰化物，该方法可轻松获得腈产品，通常收率良好，收率极佳。该反应是通过使用Ni II配合物作为预催化剂和DMAP作为添加剂来完成的。该方法还显示了广泛的功能组兼容性。例如，在反应过程中，酮，甲氧基，N，N-二甲基氨基，氰基，酯和吡啶基具有良好的耐受性。
• Well-Defined Air-Stable Palladium HASPO Complexes for Efficient Kumada-Corriu Cross-Couplings of (Hetero)Aryl or Alkenyl Tosylates
  作者：Lutz Ackermann、Anant R. Kapdi、Sabine Fenner、Christoph Kornhaaß、Carola Schulzke

  DOI：10.1002/chem.201002386

  日期：2011.3.1

  Palladium complexes of representative heteroatom‐substituted secondary phosphine oxide (HASPO) preligands were synthesized and fully characterized, including X‐ray crystal structure analysis. Importantly, these well‐defined complexes served as highly efficient catalysts for Kumada–Corriu cross‐coupling reactions of aryl, alkenyl, and even heteroaryl tosylates. Particularly, an air‐stable catalyst derived

  代表的钯络合物ħ etero一汤姆取代小号econdary p hosphine ø西德（HASPO）preligands合成并充分表征，包括X射线晶体结构分析。重要的是，这些定义明确的络合物可作为Kumada-Corriu芳基，烯基乃至杂芳基甲苯磺酸酯交叉偶联反应的高效催化剂。特别是，由廉价的PinP（O）H衍生的空气稳定型催化剂显示出极高的催化效力，这导致在极低的反应条件下，在足够宽泛的反应条件下，低催化剂负载下的交叉偶联。
• Preparation of Enamides via Palladium-Catalyzed Amidation of Enol Tosylates
  作者：Artis Klapars、Kevin R. Campos、Cheng-yi Chen、Ralph P. Volante

  DOI：10.1021/ol050117y

  日期：2005.3.1

  [GRAPHICS]A Pd-catalyzed coupling of enol tosylates and amides has been developed. Ligand screening revealed dipf as the most general ligand for this transformation. A variety of enol tosylates were coupled to an array of enamides in 58-97% yield.
• Preparation of α,β-unsaturated esters and amides via external-CO-free palladium-catalyzed carbonylation of alkenyl tosylates
  作者：Tsuyoshi Ueda、Hideyuki Konishi、Kei Manabe

  DOI：10.1016/j.tetlet.2012.07.057

  日期：2012.9

  monoxide nor any pressure-resistant apparatus. A variety of cyclic and acyclic alkenyl tosylates can be converted into the corresponding phenyl esters in good yields. Furthermore, this method is effective for the one-pot synthesis of α,β-unsaturated amides.

  描述了甲酸酯与甲酸苯酯的钯催化羰基化。该程序既不需要外部一氧化碳，也不需要任何耐压设备。各种环状和无环烯基甲苯磺酸盐可以良好的产率转化为相应的苯基酯。此外，该方法对于α，β-不饱和酰胺的一锅法合成是有效的。
• A Versatile Catalyst System for Suzuki−Miyaura Cross-Coupling Reactions of C(sp²)-Tosylates and Mesylates
  作者：Brijesh Bhayana、Brett P. Fors、Stephen L. Buchwald

  DOI：10.1021/ol9015892

  日期：2009.9.3

  A catalyst system for the Suzuki-Miyaura cross-coupling reactions of aryl and vinyl tosylates and mesylates has been developed. This catalyst displays excellent functional group tolerance and allows the coupling of heteroarylboronic acids with aryl tosylates and mesylates to be performed in high yields. Moreover, reactions employing alkylboronic acids, as well as heteroaryl, vinyl, and allylic pinacol boronate esters, were conducted with high efficiencies.