2-(2-naphthalen-1-yl-allyloxy)tetrahydropyran | 853401-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-naphthalen-1-yl-allyloxy)tetrahydropyran
• 英文别名: 2H-Pyran, tetrahydro-2-[[2-(1-naphthalenyl)-2-propenyl]oxy]-；2-(2-naphthalen-1-ylprop-2-enoxy)oxane
• CAS: 853401-63-5
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: ZWWNUFJHYQDRHE-UHFFFAOYSA-N

物化性质

• 沸点：
  423.2±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-chloroallyloxy)-tetrahydropyran 、 1-萘硼酸 在 bis(η3-allyl-μ-chloropalladium(II)) cis,cis,cis-1,2,3,4-tetrakis (diphenylphosphinomethyl)cyclopentane 、 potassium carbonate 作用下， 以 xylene 为溶剂， 反应 20.0h， 以38%的产率得到2-(2-naphthalen-1-yl-allyloxy)tetrahydropyran
  参考文献：
  名称：

  Suzuki Coupling of 2‐Chloroacrylonitrile, Methyl 2‐Chloroacrylate, or 2‐Chloroprop‐1‐en‐3‐ol with Arylboronic Acids Catalyzed by a Palladium‐Tetraphosphine Complex

  摘要：

  The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane (Tedicyp) in combination with [Pd(C3H5)Cl](2) affords an efficient catalyst of the coupling of 2-chloroacrylonitrile with arylboronic acids. In the presence of 1% catalyst, the 2-arylacrylonitrile derivatives were obtained in medium to good yields. A variety of substituents such as alkyl, methoxy, fluoro, trifluoromethyl, formyl, or nitro on the arylboronic acid are tolerated. The cross-coupling reactions of methyl 2-chloroacrylate with arylboronic acids give simple access to 2-phenylacrylate derivatives, which are useful precursors for the synthesis of biologically active compounds such as ibuprofen, ketoprofen, and naproxen.

  DOI：

  10.1080/00397910600773866

文献信息

• Heck Reaction of Protected Allyl Alcohols with Aryl Bromides Catalyzed by a Tetraphosphanepalladium Complex
  作者：Florian Berthiol、Henri Doucet、Maurice Santelli

  DOI：10.1002/ejoc.200400797

  日期：2005.4

  A range of aryl bromides undergo a Heck vinylation reaction with a protected allyl alcohol in the presence of[PdCl(C3H5)]2/cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphan-ylmethyl)cyclopentane as a catalyst. The reactivity of these allyl alcohol derivatives using a variety of protecting groups has been studied. The best results in terms of substrate/catalyst ratio were obtained with a THP protecting

  在[PdCl(C3H5)]2/cis,cis,cis-1,2,3,4-四(二苯基膦基甲基)环戊烷存在下，一系列芳基溴化物与受保护的烯丙醇发生Heck乙烯基化反应催化剂。已经研究了使用各种保护基团的这些烯丙醇衍生物的反应性。使用 THP 保护基团获得了在底物/催化剂比方面的最佳结果。在大多数情况下，获得的主要异构体是 (E)-肉桂醇衍生物。该反应耐受多种官能团，例如三氟甲基、甲氧基、二甲氨基、乙酰基、甲酰基或腈。此外，这种催化剂可以在低负载下使用，甚至可以用于与空间位阻底物的反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Suzuki Coupling of 2‐Chloroacrylonitrile, Methyl 2‐Chloroacrylate, or 2‐Chloroprop‐1‐en‐3‐ol with Arylboronic Acids Catalyzed by a Palladium‐Tetraphosphine Complex
  作者：Florian Berthiol、Henri Doucet、Maurice Santelli

  DOI：10.1080/00397910600773866

  日期：2006.10

  The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane (Tedicyp) in combination with [Pd(C3H5)Cl](2) affords an efficient catalyst of the coupling of 2-chloroacrylonitrile with arylboronic acids. In the presence of 1% catalyst, the 2-arylacrylonitrile derivatives were obtained in medium to good yields. A variety of substituents such as alkyl, methoxy, fluoro, trifluoromethyl, formyl, or nitro on the arylboronic acid are tolerated. The cross-coupling reactions of methyl 2-chloroacrylate with arylboronic acids give simple access to 2-phenylacrylate derivatives, which are useful precursors for the synthesis of biologically active compounds such as ibuprofen, ketoprofen, and naproxen.