naphthalen-1-ylmethyl 2-acetyl-4-oxohexanoate | 1234581-56-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalen-1-ylmethyl 2-acetyl-4-oxohexanoate
• CAS: 1234581-56-6
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: WYMIIGKSQARKBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  naphthalen-1-ylmethyl 2-acetyl-4-oxohexanoate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三丁基膦 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以77%的产率得到
  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：

  naphth-1-ylmethyl acetoacetate 、 溴丁酮 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 naphthalen-1-ylmethyl 2-acetyl-4-oxohexanoate
  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