methyl 2-bromo-3-(naphthalen-2-yl)acrylate | 359400-11-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 2-bromo-3-(naphthalen-2-yl)acrylate
• 英文别名: Methyl 2-bromo-3-naphthalen-2-ylprop-2-enoate
• CAS: 359400-11-6
• 化学式: C₁₄H₁₁BrO₂
• 分子量: 291.144
• InChiKey: CVDVIPNUEWTUHV-UHFFFAOYSA-N

物化性质

• 沸点：
  396.5±22.0 °C(predicted)
• 密度：
  1.474±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-bromo-3-(naphthalen-2-yl)acrylate 在 copper(l) iodide 、 四(三苯基膦)钯 吗啉 、 N-乙基哌啶 、 碘 、 二异丁基氢化铝 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 10-Iodo-2-(naphthalen-2-ylmethylidene)deca-3,9-diyn-1-ol
  参考文献：
  名称：

  Intramolecular Nozaki–Hiyama–Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes

  摘要：

  A general and facile synthesis of the 3-substituted 10-membered ring enediynes 18-22 from the aldehydes 8 and 15 has been established by utilizing the intramolecular Nozaki-Hiyama-Kishi reaction and the lwanthanide(III)-catalyzed rearrangement of allylic alkoxyacetates as the key steps. This work provides ready access to the (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes, which can be converted into the bioactive enediynes under physiological conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00707-9
• 作为产物：
  描述：

  2,3-Dibromo-3-naphthalen-2-yl-propionic acid methyl ester 在 三乙胺 作用下， 生成 methyl 2-bromo-3-(naphthalen-2-yl)acrylate
  参考文献：
  名称：

  Intramolecular Nozaki–Hiyama–Kishi reactions and Ln(III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes

  摘要：

  A general and facile synthesis of the 3-substituted 10-membered ring enediynes 18-22 from the aldehydes 8 and 15 has been established by utilizing the intramolecular Nozaki-Hiyama-Kishi reaction and the lwanthanide(III)-catalyzed rearrangement of allylic alkoxyacetates as the key steps. This work provides ready access to the (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes, which can be converted into the bioactive enediynes under physiological conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00707-9

文献信息

• Palladium-Catalyzed Construction of Polycyclic Heterocycles by an Alkyne Insertion and Direct Arylation Cascade
  作者：Hiroaki Ohno、Tetsuaki Tanaka、Mio Yamamoto、Mutsumi Iuchi、Nobutaka Fujii

  DOI：10.1055/s-0030-1260098

  日期：2011.8

  Cascade cyclization of bromoenynes bearing an aryl group with catalytic amounts of palladium(II) acetate and cesium carbonate led to the direct construction of tri- or tetracyclic heterocycles. Direct arylation of a pyrrole, furan or thiophene ring in the cascade reaction affords the corresponding fused heteroarenes in moderate to good yields. tandem reaction - palladium - polycycles - fused-ring systems

  具有催化量的乙酸钯（II）和碳酸铯的带有芳基的溴代炔的级联环化导致直接构建三环或四环杂环。级联反应中吡咯，呋喃或噻吩环的直接芳基化以中等到良好的产率提供了相应的稠合杂芳烃。 串联反应-钯-多环化合物-稠环系统-闭环
• A Novel and Convenient Protocol for Synthesis of α-Haloacrylates
  作者：Biao Jiang、Ying Dou、Xiangya Xu、Min Xu

  DOI：10.1021/ol702859y

  日期：2008.2.1

  A.novel and convenient protocol for synthesis of alpha-haloacrylates starting from phosphonium ylide and aldedyde or alcohol was described. Halodimethylsulfonium halide was used for the first time in halogenation of phosphonium ylide. Good yield as well as a high Z/E ratio were shown in representative cases, and an umpolung dimethyl sulfide-ylide species might be involved as an intermediate.