2-(3-Methoxy-2-vinylphenyl)-4,4-dimethyl-2-oxazoline | 143123-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-Methoxy-2-vinylphenyl)-4,4-dimethyl-2-oxazoline
• 英文别名: Oxazole, 2-(2-ethenyl-3-methoxyphenyl)-4,5-dihydro-4,4-dimethyl-；2-(2-ethenyl-3-methoxyphenyl)-4,4-dimethyl-5H-1,3-oxazole
• CAS: 143123-58-4
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: WXYFNWVUDKQOSS-UHFFFAOYSA-N

物化性质

• 沸点：
  354.6±35.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-Methoxy-2-vinylphenyl)-4,4-dimethyl-2-oxazoline 在 四氯化碳 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 sodium acetate 、 三苯基膦 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 (Z)-10-Methoxy-5-oxa-dibenzo[a,e]cycloocten-6-one
  参考文献：
  名称：

  Application of an intramolecular Heck reaction for the construction of the balanol aryl core structure

  摘要：

  The highly functionalized aryl core structure of balanol has been synthesized employing a regioselective intramolecular Heck reaction as the key step. This approach can potentially lead to new types of analogues of the potent PKC inhibitor. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00907-7
• 作为产物：
  描述：

  N-(1-hydroxy-2-methylpropan-2-yl)-2,3-dimethoxybenzamide 在 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 2-(3-Methoxy-2-vinylphenyl)-4,4-dimethyl-2-oxazoline
  参考文献：
  名称：

  Application of an intramolecular Heck reaction for the construction of the balanol aryl core structure

  摘要：

  The highly functionalized aryl core structure of balanol has been synthesized employing a regioselective intramolecular Heck reaction as the key step. This approach can potentially lead to new types of analogues of the potent PKC inhibitor. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00907-7

文献信息

• β-Phenylethylamines, Indolines and Isoquinolones via Hydroamination of Styrenes by Microwave Irradiation
  作者：Julio A. Seijas、M. Pilar Vázquez-Tato、M. Montserrat Martínez

  DOI：10.1055/s-2001-14585

  日期：——

  Microwave irradiation promotes hydroamination of styrenes. This method can be used as a direct way of producing different kinds of bioactive compounds: open chain compounds like β-phenylethylamines or cyclized products like indolines or isoquinolones.

  微波辐射促进了苯乙烯的胺化反应。这种方法可作为直接合成各种生物活性化合物的途径，包括开链化合物如β-苯乙胺，以及环化产物如吲哚啉或异喹啉酮。
• Synthesis of the Benzophenone Fragment of Balanol via an Intramolecular Cyclization Event
  作者：Marie-Pierre Denieul、Bolette Laursen、Rita Hazell、Troels Skrydstrup

  DOI：10.1021/jo000750r

  日期：2000.9.1

  Studies are reported on the use of either a 7-exo radical cyclization or an intramolecular Heck reaction as the key step for the construction of the benzophenone fragment of the PKC inhibitor, balanol. Whereas, the former approach was unsuccessful, the Heck reaction proved to be viable for the coupling of two fully functionalized aryl subunits affording regioselectively a biaryl seven-membered lactone

  已有研究报道使用7-外基自由基环化或分子内Heck反应作为构建PKC抑制剂balanol的二苯甲酮片段的关键步骤。尽管前一种方法不成功，但与竞争的八元环相比，Heck反应对于两个完全官能化的芳基亚基偶联是可行的，这些亚基提供了区域选择性地以芳基亚烷基为主要成分的联芳基七元内酯。内酯。内酯的水解，然后用四氧化钌的氧化裂解烯烃，完成了苯甲酮单元的这种短暂合成。
• Reactivity of o-styryloxazolines with nucleophiles
  作者：Julio A. Seijas、M. Pilar Vazquez-Tato、Luis Castedo、Ramon J. Estevez、Maria Ruiz

  DOI：10.1021/jo00046a004

  日期：1992.9

  The reaction of o-styryl oxazolines with organollithium reagents leads to conjugated addition to the exocyclic double bond in very good yields.
• 1,6-conjugate addition to o-vinylphenyloxazolines. Syntheses of chuangxinol and 3-n-butylphthalide
  作者：M.Montserrat Martínez、M. Gabriela Ónega、M. Fe Tellado、Julio A. Seijas、M. Pilar Vázquez-Tato

  DOI：10.1016/s0040-4020(97)00914-9

  日期：1997.10

  Phtalhides are prepared from o-vinylphenyloxazolines in one pot reaction by 1,6-conjugate addition of alkyllithium and trapping or the benzylic anion with MoOPH, followed by hydrolysis with aqueous oxalic acid. This method was applied to the syntheses of two natural products: chuangxinol and 3-n-butylphthalide. (C) 1997 Elsevier Science Ltd.
• Nucleophilic aromatic substitution on (o-methoxyaryl)oxazolines. A convenient synthesis of o-alkyl-, o-alkenyl-, and o-arylbenzoic acids
  作者：A. I. Meyers、Richard Gabel、Edward D. Mihelich

  DOI：10.1021/jo00401a018

  日期：1978.3