1-methyl-1-(3-methylbut-2-en-1-yl)naphthalen-2-one | 115263-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methyl-1-(3-methylbut-2-en-1-yl)naphthalen-2-one
• 英文别名: 1-methyl-1-(3-methylbut-2-en-1-yl)naphthalen-2(1H)-one；1-Methyl-1-(3-methylbut-2-enyl)naphthalen-2-one
• CAS: 115263-73-5
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: HRUCSPZUACKXMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-1-(3-methylbut-2-en-1-yl)naphthalen-2-one 以5%的产率得到
  参考文献：
  名称：

  GERAGHTY, NIALL W. A.;MONAGHAN, MICHAEL J.;HANLEY, NOREEN M., TETRAHEDRON LETT., 28,(1987) N 40, 4729-4732

  摘要：

  DOI：
• 作为产物：
  描述：

  1-溴-2-萘酚 在 盐酸 、 甲醇 、 正丁基锂 、 potassium 2-methylbutan-2-olate 、 potassium carbonate 、 tetrabutylammonium tricarbonylnitrosylferrate 、 1,3-Di-tert-butyl-4,5-dihydro-3H-imidazol-1-ium hexafluorophosphate 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 21.0h， 生成 1-methyl-1-(3-methylbut-2-en-1-yl)naphthalen-2-one
  参考文献：
  名称：

  Iron-Catalyzed C-Allylating Partial Dearomatization of Naphthols

  摘要：

  The iron complex Bu4N[Fe(CO)(3)(NO)](TBA[Fe]) catalyzes the intermolecular allylation of naphthol derivatives to give the corresponding partially dearomatized allylated chromenones in good to excellent yields. The scope and limitations are reported. An efficient decarboxylative intramolecular C- allylation, starting from allyl naphthyl carbonates, was developed. From a mechanistic point of view, the overall process is the result of a fast O- allylation followed by a sigmatropic rearrangement to the desired product.

  DOI：

  10.1055/s-0035-1560909

文献信息

• Selective C-alkylation of substituted naphthols under non-aqueous conditions
  作者：Anni Kooli、Tatsiana Shalima、Eleana Lopušanskaja、Anne Paju、Margus Lopp

  DOI：10.1016/j.tet.2021.132278

  日期：2021.8

  A simple and selective C-alkylation of 1- and 2-naphthols with benzylic and allylic halides was developed. In an organic solvent, like cyclopentyl methyl ether, or toluene in the presence of the ether or alcohol additives, a selective ortho-addition leading to substituted naphthalenones up to 90 % was achieved.

  开发了一种简单且选择性的 1- 和 2- 萘酚与苄基和烯丙基卤化物的C-烷基化反应。在有机溶剂（如环戊基甲基醚或甲苯）中，在醚或醇添加剂的存在下，实现了选择性邻位加成，产生高达 90% 的取代萘酮。
• Photochemistry of 1-allyl-naphthalen-2(1H)-ones: A revised mechanism for the formation of benzotricyclo[3.3.1.02,7]nonen-8-ones.
  作者：Niall W.A. Geraghty、Michael J. Monaghan、Noreen M. Hanley

  DOI：10.1016/s0040-4039(00)96611-5

  日期：1987.1

  The photochemistry of a series of 1-alkenyl-naphthalen-2(1H)-ones suggests that the formation of benzotricyclo[3.3.1.02,7]nonen-8-ones involves an ambident benzyl radical which gives these products on ring closure at the cyclic carbon; ring closure at the cyclic carbon gives the normal [2+2] enone-olefin cycloaddition products.

  一系列1-烯基-萘-2（1H）-one的光化学表明，苯并三环[3.3.1.0 2,7 ] nonen -8- one的形成涉及一个环比的苄基，这些苄基在闭环时产生这些产物。的环碳; 在环状碳上的闭环得到正常的[2 + 2]烯酮-烯烃环加成产物。
• GERAGHTY, NIALL W. A.;MONAGHAN, MICHAEL J.;HANLEY, NOREEN M., TETRAHEDRON LETT., 28,(1987) N 40, 4729-4732
  作者：GERAGHTY, NIALL W. A.、MONAGHAN, MICHAEL J.、HANLEY, NOREEN M.

  DOI：——

  日期：——
• Iron-Catalyzed C-Allylating Partial Dearomatization of Naphthols
  作者：Bernd Plietker、Berenice Heid

  DOI：10.1055/s-0035-1560909

  日期：——

  The iron complex Bu4N[Fe(CO)(3)(NO)](TBA[Fe]) catalyzes the intermolecular allylation of naphthol derivatives to give the corresponding partially dearomatized allylated chromenones in good to excellent yields. The scope and limitations are reported. An efficient decarboxylative intramolecular C- allylation, starting from allyl naphthyl carbonates, was developed. From a mechanistic point of view, the overall process is the result of a fast O- allylation followed by a sigmatropic rearrangement to the desired product.