(E)-4-benzylidene-3-methyl-1-oxo-1,2,3,4-tetrahydro-2-oxanaphthalene

• 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: (E)-4-benzylidene-3-methyl-1-oxo-1,2,3,4-tetrahydro-2-oxanaphthalene
• 英文别名: (Z)-4-benzylidene-3-methylisochroman-1-one；4-benzylidene-3-methylisochroman-1-one；(4Z)-4-benzylidene-3-methylisochromen-1-one
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: KEDHWBHBLWCLKW-LFIBNONCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (E)-4-benzylidene-3-methyl-1-oxo-1,2,3,4-tetrahydro-2-oxanaphthalene 在 tris(acetonitrile)pentamethylcyclopentadienylrhodium(III) hexafluoroantimonate 、 copper diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 22.0h， 以69%的产率得到
  参考文献：
  名称：

  Rh(III)-Catalyzed Coupling of Benzamides with Propargyl Alcohols via Hydroarylation–Lactonization

  摘要：

  Rh(III)-catalyzed C-H activation and annulation of 1-benzoylpyrrolidine with propargyl alcohols has been achieved for an efficient synthesis of (4-benzylidene)isochroman-1-one. Highly enantioenriched products were obtained starting from optically pure propargyl alcohols.

  DOI：

  10.1021/ol403166p
• 作为产物：
  描述：

  N,N-二乙基苯甲酰胺 、 4-苯基-3-丁炔-2-醇 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 三甲基乙酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以39%的产率得到(E)-4-benzylidene-3-methyl-1-oxo-1,2,3,4-tetrahydro-2-oxanaphthalene
  参考文献：
  名称：

  Rh(III)-Catalyzed Coupling of Benzamides with Propargyl Alcohols via Hydroarylation–Lactonization

  摘要：

  Rh(III)-catalyzed C-H activation and annulation of 1-benzoylpyrrolidine with propargyl alcohols has been achieved for an efficient synthesis of (4-benzylidene)isochroman-1-one. Highly enantioenriched products were obtained starting from optically pure propargyl alcohols.

  DOI：

  10.1021/ol403166p

文献信息

• Regioselective C−H Hydroarylation of Internal Alkynes with Arenecarboxylates: Carboxylates as Deciduous Directing Groups
  作者：Liangbin Huang、Agostino Biafora、Guodong Zhang、Valentina Bragoni、Lukas J. Gooßen

  DOI：10.1002/anie.201600894

  日期：2016.6.6

  catalytic [Ru(p‐cym)I2]2 and the base guanidine carbonate, benzoic acids react with internal alkynes to give the corresponding 2‐vinylbenzoic acids. This alkyne hydroarylation is generally applicable to diversely substituted electron‐rich and electron‐poor benzoic and acrylic acids. Aryl(alkyl)acetylenes react regioselectively with formation of the alkyl‐branched hydroarylation products, and propargylic

  在催化[Ru（p- cym）I 2 ] 2的存在下与碱式碳酸胍，苯甲酸与内部炔烃反应，生成相应的2-乙烯基苯甲酸。这种炔烃的氢芳基化反应通常适用于各种取代的富电子和贫电子的苯甲酸和丙烯酸。芳基（烷基）乙炔区域选择性地反应，形成烷基支链的氢芳基化产物，炔丙醇转化为γ-亚烷基-δ-内酯。加氢芳基化反应也可以用不同选择的催化剂和反应条件进行脱羧反应。该反应变体不会通过2-乙烯基苯甲酸的中间形成来进行，从而打开了区域选择性，废物最少化的乙烯基芳烃的合成入口。
• Stereochemistry of the Asymmetric Carbopalladation of Allenes Followed by Nucleophilic Substitution Reactions with Carbo- and Aminonucleophiles
  作者：Fumiko Kato、Kunio Hiroi

  DOI：10.1248/cpb.52.95

  日期：——

  The stereochemistry of the asymmetric palladium-catalyzed reaction of allenes with iodobenzene followed by nucleophilic substitution reaction with sodium malonate and N-methylbenzylamine is described. On the basis of the absolute configuration of the product and the stereochemical result of a similar reaction of a chiral allene, the mechanism of the above asymmetric reactions is discussed.

  描述了烯丙基与碘苯的不对称钯催化反应，然后与丙二酸钠和N-甲基苄胺进行亲核取代反应的立体化学。根据产物的绝对构型和手性烯丙基类似反应的立体化学结果，讨论了上述不对称反应的机理。
• Rh(III)-Catalyzed Coupling of Benzamides with Propargyl Alcohols via Hydroarylation–Lactonization
  作者：Fen Wang、Zisong Qi、Jiaqiong Sun、Xuelin Zhang、Xingwei Li

  DOI：10.1021/ol403166p

  日期：2013.12.20

  Rh(III)-catalyzed C-H activation and annulation of 1-benzoylpyrrolidine with propargyl alcohols has been achieved for an efficient synthesis of (4-benzylidene)isochroman-1-one. Highly enantioenriched products were obtained starting from optically pure propargyl alcohols.