4-methylisochroman-3-one | 122571-80-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-methylisochroman-3-one
• 英文别名: 4-methyl-2-benzopyran-3-one；4-Methyl-1,4-dihydroisochromen-3-one
• CAS: 122571-80-6
• 化学式: C₁₀H₁₀O₂
• 分子量: 162.188
• InChiKey: IBBXAYTUXVHVSS-UHFFFAOYSA-N

物化性质

• 熔点：
  44-45 °C
• 沸点：
  326.4±31.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  4-methylisochroman-3-one 在 sodium tetrahydroborate 、 五氯化磷 作用下， 以 乙醇 为溶剂， 反应 31.0h， 生成 (+/-)-2,3-dimethoxy-13-methylberbine
  参考文献：
  名称：

  Mali, R. S.; Patil, Sharadbala D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 887 - 890

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基-1-苯乙胺 在 正丁基锂 作用下， 反应 26.0h， 生成 4-methylisochroman-3-one
  参考文献：
  名称：

  Mali, R. S.; Patil, Sharadbala D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 887 - 890

  摘要：

  DOI：

文献信息

• A Palladium-Catalyzed Regioselective Hydroesterification of Alkenylphenols to Lactones with Phenyl Formate as CO Source
  作者：Haining Wang、Ben Dong、Yang Wang、Jingfu Li、Yian Shi

  DOI：10.1021/ol403171p

  日期：2014.1.3

  An effective Pd(OAc)2-PPh3 catalyzed hydroesterification of alkenylphenols with phenyl formate as CO surrogate is described. A variety of lactones are obtained in generally high yields with high regioselectivities. In one case, 76% ee is obtained with a chiral ligand.

  描述了一种有效的Pd（OAc）2 -PPh 3催化烯基苯酚与甲酸苯酯作为CO替代物的加氢酯化反应。通常以高产率和高区域选择性获得各种内酯。在一种情况下，使用手性配体获得76％的ee。
• Imidazole Derivatives as Accelerators for Ruthenium-Catalyzed Hydroesterification and Hydrocarbamoylation of Alkenes: Extensive Ligand Screening and Mechanistic Study
  作者：Hideyuki Konishi、Takashi Muto、Tsuyoshi Ueda、Yayoi Yamada、Miyuki Yamaguchi、Kei Manabe

  DOI：10.1002/cctc.201402986

  日期：2015.3

  Imidazole derivatives are effective ligands for promoting the [Ru3(CO)12]‐catalyzed hydroesterification of alkenes using formates. Extensive ligand screening was performed to identify 2‐hydroxymethylated imidazole as the optimal ligand. Neither carbon monoxide gas nor a directing group was required, and the reaction also showed a wide substrate generality. The Ru–imidazole catalyst system also promoted

  咪唑衍生物是使用甲酸酯促进[Ru 3（CO）12 ]催化的烯烃加氢酯化反应的有效配体。进行了广泛的配体筛选，以确定2-羟甲基化的咪唑为最佳配体。既不需要一氧化碳气体也不需要引导基团，并且该反应还显示出广泛的底物通用性。Ru-咪唑催化剂体系还促进了分子内的氨基甲酰化作用，以提供内酰胺。通过X射线晶体学分析明确地分析了Ru-咪唑配合物，它具有源自[[Ru 3（CO）12 ]和两个配体的三核结构。该配合物也已成功用于加氢酯化。通过使用D详细检查了该机制－和13 C标记的甲酸酯，表明加氢酯化反应是通过脱羰基－再羰基化途径进行的。
• Synthesis of multi-substituted cyclobutenes: Cyclic strategy for [2 + 2] cycloaddition of ketene silyl acetals with propiolates
  作者：Yousuke Yamaoka、Motoki Ueda、Tohru Yamashita、Kazuma Shimoda、Ken-ichi Yamada、Kiyosei Takasu

  DOI：10.1016/j.tetlet.2017.06.039

  日期：2017.7

  Cyclic ketene silyl acetals were utilized for [2 + 2] cycloaddition with propiolates to prevent an undesired electrocyclic ring opening reaction. Trimethylaluminum catalyzed this cycloaddition to afford the cyclobutene derivatives in high yields. The advantage of this reaction was highlighted by the successful application of β-substituted propiolates to afford the multi-substituted cyclobutenes. Furthermore

  环状乙烯酮甲硅烷基缩醛用于与丙酸酯的[2 + 2]环加成反应，以防止发生不希望的电环开环反应。三甲基铝催化该环加成反应以高收率提供环丁烯衍生物。通过成功地应用β-取代的丙酸酯提供多取代的环丁烯，突出了该反应的优点。此外，我们将此方法应用于天然产物青蒿素的后期功能化。
• Torquoselectivity in the electrocyclic conversion of benzocyclobutenes to o-xylylenes
  作者：Charles W. Jefford、Gerald Bernardinelli、Ying Wang、David C. Spellmeyer、Andrzej Buda、K. N. Houk

  DOI：10.1021/ja00030a005

  日期：1992.2

  conrotatory electrocyclic opening of benzocyclobutene to o-xylylene was studied by means of ab initio molecular orbital calculations. The theory developed earlier to predict the torquoselectivity of ring opening of J-substituted cyclobutenes was found to be applicable. Experimentally, the ring opening of several 7-substituted benzocyclobutenes, such as the cyano, methoxycarbonyl, and formyl derivatives was

  通过从头算分子轨道计算研究了苯并环丁烯向邻二甲苯的旋转电环开环。发现较早开发的用于预测 J-取代环丁烯开环扭矩选择性的理论是适用的。通过实验，研究了几种 7-取代的苯并环丁烯的开环，例如氰基、甲氧基羰基和甲酰基衍生物。得到邻二甲苯，其中氰基或酯基向外旋转，而甲酰基向内旋转
• Palladium-Catalyzed Intramolecular Hydroaminocarbonylation to Lactams: Additive-Free Protocol Initiated by Palladium Hydride
  作者：Yue Hu、Zhiqiang Shen、Hanmin Huang

  DOI：10.1021/acscatal.6b01939

  日期：2016.10.7

  A palladium-catalyzed intramolecular hydroaminocarbonylation of 2-vinylbenzylamines in the absence of acidic or any other additives was realized via rational designing the catalytic system on the basis of mechanistic studies, which allows for the synthesis of a variety of six-membered lactams in good to excellent yields with high regioselectivity. The postulated palladium-hydride intermediate for initiating

  通过在机理研究的基础上合理设计催化体系，实现了在不存在酸性添加剂或任何其他添加剂的情况下，钯催化的2-乙烯基苄胺的分子内氢氨基羰基化反应，从而可以合成多种六元内酰胺具有高区域选择性的优异产量。已经确定了用于引发氢氨基羰基化的假定的氢化钯氢化物中间体，并将其直接用作反应的催化剂。进一步的动力学研究表明，以氢化钯为催化剂，反应速率为负一阶依赖于底物浓度。