1-Methyl-1-(prop-2-enyl)-naphthalen-2(1H)-one | 39094-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Methyl-1-(prop-2-enyl)-naphthalen-2(1H)-one
• 英文别名: 1-allyl-1-methylnaphthalen-2-one；1-Allyl-1-methyl-2-oxo-1,2-dihydro-naphthalin；1-Allyl-1-methyl-2-naphthalenon；1-Methyl-1-prop-2-enylnaphthalen-2-one
• CAS: 39094-46-7
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: VFPLKOCKWUSNGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 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-(prop-2-enyl)-naphthalen-2(1H)-one 以10%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-乙酰氧基-1-甲基-1H-萘-2-酮 在 copper(I) chloride 作用下， 以 乙醚 为溶剂， 生成 1-Methyl-1-(prop-2-enyl)-naphthalen-2(1H)-one
  参考文献：
  名称：

  Reactions of cyclohexadienones. XXXVI. Allyl and benzyl migrations in the rearrangements of naphthalenones

  摘要：

  DOI：

  10.1021/ja00424a036

文献信息

• Palladium-Catalyzed Intermolecular Allylic Dearomatization Reaction of α-Substituted β-Naphthol Derivatives: Scope and Mechanistic Investigation
  作者：Chun-Xiang Zhuo、Shu-Li You

  DOI：10.1002/adsc.201400154

  日期：2014.6.16

  A highly efficient dearomatization reaction of α‐substituted β‐naphthols with excellent chemoselectivity and regioselectivity has been developed. Mechanistic studies demonstrated that the dearomatized alkylation product is the thermodynamically more stable compound. The etherification product could be further transformed to the dearomatization product.

  已经开发出一种高效的α-取代的β-萘酚脱芳香化反应，具有出色的化学选择性和区域选择性。机理研究表明，脱芳烃化的烷基化产物是热力学上更稳定的化合物。醚化产物可以进一步转化为脱芳烃化产物。
• Umlagerung von Allyl-aryläthern und Allyl-cyclohexadienonen mittels Bortrichlorid
  作者：J. Borgulya、R. Madeja、P. Fahrni、Hans-Jürgen Hansen、Hans Schmid、R. Barner

  DOI：10.1002/hlca.19730560103

  日期：1973.1.31

  exception of allyl 3-methoxyphenyl ether (5), m-substituted allyl aryl ethers show similar behaviour (with respect to the composition of the product mixture) to that observed in the thermal rearrangement (Table 3). The rearrangement of allyl aryl ethers with an alkyl group in the o-position, in the prescence of boron trichloride, yields a mixture of o- and p-allyl phenols, where more p-product is present

  没有强电子吸引性取代基的烯丙基芳基醚在低温下在0.7摩尔三氯化硼在氯苯中的低温下经历电荷诱导的[3 s，3 s]σ重排，在水解后得到相应的邻烯丙基苯酚（表1和2）。相对于约10 10的热克莱森重排，电荷感应引起反应速率的增加。用烯丙基3-甲氧基苯基醚的例外（5） ，米-取代的烯丙基芳基醚显示出类似的行为（相对于所述产物的混合物的组合物）到的是，在热重排观察到（表3）。烯丙基芳基醚在烷基中的重排o位置在三氯化硼泛黄时会生成o-和p-烯丙基苯酚的混合物，其中p-产物的存在要多于热重排对应的产物混合物中的p-产物（表4）。对于邻烷基化的α-甲基烯丙基芳基醚，这种“对位效应”尤其明显（表5）。
• 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。
• [3,5]-Sigmatropic shifts in the photochemistry of 1-allyl-naphthalen-2(1H)-ones
  作者：Patrick D. Cunningham、Niall W. A. Geraghty、Noreen M. Hanly、Patrick J. McArdle

  DOI：10.1039/c39850001698

  日期：——

  2a,3,4,8b-tetrahydro-1,4-methanocyclobuta[a]naphthalen-2[1H]-one (2) in the photolysis of 1-methyl-1-(prop-2-enyl)-naphthalen-2(1H)-one (5) is confirmed by X-ray crystallography of the corresponding 7-bromo photoproduct (3), the available evidence does not support the previously made suggestion that this occurs via a [3,5]-sigmatropic shift; an alternative mechanism involving an arene-alkene exciplex

  虽然在1-甲基-1-（丙-2-烯基）的光解中形成了2a，3,4,8b-四氢-1,4-甲基环丁[ a ]萘-2 [1 H ]-一（2）萘-2（1 H）-1 （5）通过相应的7-溴感光产物（3）的X射线晶体学证实，现有证据不支持先前通过[3，3 5]-正相移；提出了涉及芳烃-烯烃激基复合物的替代机制。
• 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.