Naphthalen-1-ylmethyl 3-trimethylsilylprop-2-ynoate | 1234580-91-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Naphthalen-1-ylmethyl 3-trimethylsilylprop-2-ynoate
• 英文别名: naphthalen-1-ylmethyl 3-trimethylsilylprop-2-ynoate
• CAS: 1234580-91-6
• 化学式: C₁₇H₁₈O₂Si
• 分子量: 282.414
• InChiKey: GSIZPWWADQTFGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  Naphthalen-1-ylmethyl 3-trimethylsilylprop-2-ynoate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以89%的产率得到1-(trimethylsilyl)-3-(naphth-1-yl)prop-1-yne
  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：

  3-(三甲基硅基)丙炔酸 、 1-萘甲醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Naphthalen-1-ylmethyl 3-trimethylsilylprop-2-ynoate
  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

文献信息

• 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.