3-(6-methoxynaphthalen-2-yl)propiolaldehyde | 1221590-67-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(6-methoxynaphthalen-2-yl)propiolaldehyde
• 英文别名: 3-(6-Methoxynaphthalen-2-yl)prop-2-ynal；3-(6-methoxynaphthalen-2-yl)prop-2-ynal
• CAS: 1221590-67-5
• 化学式: C₁₄H₁₀O₂
• 分子量: 210.232
• InChiKey: WYYRYIHFFMHCFN-UHFFFAOYSA-N

物化性质

• 沸点：
  398.2±15.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(6-methoxynaphthalen-2-yl)propiolaldehyde 在 三乙烯二胺 、 十六烷基三甲基溴化铵 作用下， 反应 4.0h， 以77%的产率得到(4-((6-methoxynaphthalen-2-yl)ethynyl)-4H-pyran-3,5-diyl)bis((6-methoxynaphthalen-2-yl)methanone)
  参考文献：
  名称：

  Micelle‐Mediated Trimerization of Ynals to Orthogonally Substituted 4 H ‐Pyrans in Water: Downstream Rearrangement to Bioactive 2,8‐dioxabicyclo[3.3.1]nona‐3,6‐diene Frameworks

  摘要：

  AbstractAn efficient trimerization of ynals to diversely substituted 4H‐pyran constructs has been executed in water, under ambient conditions employing micellar catalysis. The method is in agreement with the ideas of green and sustainable chemistry. The locus of the micellar reaction site has been probed through proton NMR studies. A general acid‐mediated downstream rearrangement of the derived 4H‐pyrans to interesting 2,8‐dioxabicyclo[3.3.1]nona‐3,6‐dienes has been observed.

  DOI：

  10.1002/ejoc.202101122
• 作为产物：
  描述：

  在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.17h， 生成 3-(6-methoxynaphthalen-2-yl)propiolaldehyde
  参考文献：
  名称：

  Micelle‐Mediated Trimerization of Ynals to Orthogonally Substituted 4 H ‐Pyrans in Water: Downstream Rearrangement to Bioactive 2,8‐dioxabicyclo[3.3.1]nona‐3,6‐diene Frameworks

  摘要：

  AbstractAn efficient trimerization of ynals to diversely substituted 4H‐pyran constructs has been executed in water, under ambient conditions employing micellar catalysis. The method is in agreement with the ideas of green and sustainable chemistry. The locus of the micellar reaction site has been probed through proton NMR studies. A general acid‐mediated downstream rearrangement of the derived 4H‐pyrans to interesting 2,8‐dioxabicyclo[3.3.1]nona‐3,6‐dienes has been observed.

  DOI：

  10.1002/ejoc.202101122

文献信息

• Stereoselective Oxa‐Michael Addition of Tyrosine to Propargyl Aldehyde/Esters: Formation of Benzofurans and Flavones
  作者：Stanley N. S. Vasconcelos、Isadora Maria Oliveira、Anwar Shamim、Julio Zukerman‐Schpector、Daniel C. Pimenta、Hélio A. Stefani

  DOI：10.1002/adsc.201900564

  日期：2019.9.17

  oxa‐Michael addition of the phenol moiety present in tyrosine and 3‐iodotyrosine to different propargyl aldehydes delivered products with predominantly Z stereochemistry, as evidenced by X‐ray crystallography analysis. When ethyl propiolate was used as the propargyl ester source, the products were achieved with exclusively E stereochemistry with yields ranging from 17% to 91%. The oxa‐Michael addition compounds

  X射线晶体学分析证明，酪氨酸和3-碘酪氨酸中存在的苯酚部分的立体选择性oxa-Michael加成到不同的炔丙基醛中，所产生的产物主要具有Z立体化学。当使用丙酸乙酯作为炔丙基酯源时，仅用E即可获得产物立体化学，收率从17％到91％。在五元和六元杂环化合物的合成中，氧杂-迈克尔加成化合物充当底物。施加到反应介质上的气氛直接影响产物的形成。当施加惰性氮气气氛时，通过Heck分子内反应选择性地获得了2-芳基-3-甲酰基-5-丙氨酰基苯并呋喃核，而在一氧化碳气氛下进行的反应仅导致了6-丙氨酰基-2-苯并呋喃。芳基黄酮衍生物通过还原性分子内酰化作用。
• Gold-Catalyzed Benzannulation of 3-Alkoxy-1,5-enynes: Access to Functionalized Benzenes
  作者：Guijie Li、Yuanhong Liu

  DOI：10.1021/jo100137j

  日期：2010.5.7

  A cationic Au(I) complex catalyzed benzannulation of 3-alkoxy-1,5-enynes bridged by a cyclopropyl ring with a variety of nucleophiles is described. The reaction occurs selectively through a 6-endo-dig pathway to provide tri- and tetrasubstituted benzenes efficiently under mild reaction conditions.