1-naphthylmethyl 3-phenylpropynoate | 129957-21-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-naphthylmethyl 3-phenylpropynoate
• 英文别名: Naphthalen-1-ylmethyl 3-phenylprop-2-ynoate
• CAS: 129957-21-7
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: WLHUOURDEMIZSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  1-naphthylmethyl 3-phenylpropynoate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以88%的产率得到3-(1-naphthyl)-1-phenyl-1-propyne
  参考文献：
  名称：

  Decarboxylative Benzylations of Alkynes and Ketones

  摘要：

  Benzyl esters of propiolic and beta-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.

  DOI：

  10.1021/ja1035557
• 作为产物：
  描述：

  1-萘甲醇 、 苯丙炔酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 1-naphthylmethyl 3-phenylpropynoate
  参考文献：
  名称：

  Anderson, Mark R.; Brown, Roger F. C.; Coulston, Karen J., Australian Journal of Chemistry, 1990, vol. 43, # 7, p. 1137 - 1150

  摘要：

  DOI：

文献信息

• Highly Stereoselective Generation of Complex <i>Oxy</i>-Bicyclic Scaffolds <i>via</i> an Atom-Economic Pd(II)-Catalyzed Hydroalkynylation, Isomerization and Diels–Alder Cycloaddition Sequence
  作者：Ruwei Shen、Ke Chen、Qiulin Deng、Jianjun Yang、Lixiong Zhang

  DOI：10.1021/ol500101b

  日期：2014.2.21

  Pd(II)-catalyzed hydroalkynylation, alkyne-allene isomerization, and Diels–Alder cycloaddition is reported. The reaction employs readily available starting substrates, proceeds in a highly ordered fashion, features high regio- and stereoselectivity, and tolerates a wide range of functionality and structural motifs, thus offering an attractive strategy for producing new molecular complexity and diversity from easily

  据报道，一种原子经济串联的Pd（II）催化的加氢炔基化反应，炔烃-丙二烯异构化反应和Diels-Alder环加成反应。该反应采用容易获得的起始底物，以高度有序的方式进行，具有很高的区域选择性和立体选择性，并具有广泛的功能和结构基序，因此提供了一种诱人的策略，可利用易于获得的起始原料来产生新的分子复杂性和多样性。进行了具有密度泛函理论计算的机理研究，以合理化所观察到的立体选择性。
• Anderson, Mark R.; Brown, Roger F. C.; Coulston, Karen J., Australian Journal of Chemistry, 1990, vol. 43, # 7, p. 1137 - 1150
  作者：Anderson, Mark R.、Brown, Roger F. C.、Coulston, Karen J.、Eastwood, Frank W.、Ward, Annemarie

  DOI：——

  日期：——
• ANDERSON, MARK R.;BROWN, ROGER F. C.;COULSTON, KAREN J.;EASTWOOD, FRANK W+, AUSTRAL. J. CHEM., 43,(1990) N, C. 1137-1150
  作者：ANDERSON, MARK R.、BROWN, ROGER F. C.、COULSTON, KAREN J.、EASTWOOD, FRANK W+

  DOI：——

  日期：——
• Decarboxylative Benzylations of Alkynes and Ketones
  作者：Robert R. P. Torregrosa、Yamuna Ariyarathna、Kalicharan Chattopadhyay、Jon A. Tunge

  DOI：10.1021/ja1035557

  日期：2010.7.14

  Benzyl esters of propiolic and beta-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.