methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate | 1258518-21-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate
• 英文别名: Methyl 2-hydroxy-3-methylidene-5-phenylcyclohexene-1-carboxylate；methyl 2-hydroxy-3-methylidene-5-phenylcyclohexene-1-carboxylate
• CAS: 1258518-21-6
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: HDMUDOIBHHXHNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 1-(methoxy(methyl)carbamoyl)-2-phenylcyclopropane-1-carboxylate 在 indium(III) triflate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 methyl 2-hydroxy-3-methylene-5-phenylcyclohex-1-enecarboxylate
  参考文献：
  名称：

  烯基环丙基酮的铟催化均一-Nazarov环化反应

  摘要：

  在此，报道了用于烯基环丙基酮的均一纳扎罗夫环化的有效路易斯酸催化方案。带有β-氢（或甲硅烷基）的烯烃提供亚甲基环己醇和环己烯酮的1.5：1混合物。当不存在β-氢（或甲硅烷基）时，仅观察到环己烯酮。在温和的条件下，产品以高至高收率（高达93％）的速度迅速形成，并且很容易衍生化。

  DOI：

  10.1021/ol102497w

文献信息

• Catalysis and Chemodivergence in the Interrupted, Formal Homo-Nazarov Cyclization Using Allylsilanes
  作者：Raynold Shenje、Corey W. Williams、Katherine M. Francois、Stefan France

  DOI：10.1021/ol503305r

  日期：2014.12.19

  A chemodivergent, Lewis acid catalyzed allylsilane interrupted formal homo-Nazarov cyclization is disclosed. With catalytic amounts of SnCl4 and in the presence of allyltrimethylsilane, a formal HosomiSakurai-type allylation of the oxyallyl cation intermediate is observed. A variety of functionalized donoracceptor cyclopropanes and allylsilanes were shown to be amenable to the reaction transformation and the allyl products were formed in up to 92% yield. Under dilute reaction conditions with stoichiometric SnCl4 and at reduced temperatures, an unusual formal [3 + 2]-cycloaddition between the allylsilane and the oxyallyl cation occurred to give hexahydrobenzofuran products in up to 69% yield.
• Indium-Catalyzed Homo-Nazarov Cyclizations of Alkenyl Cyclopropyl Ketones
  作者：Dadasaheb V. Patil、Lien H. Phun、Stefan France

  DOI：10.1021/ol102497w

  日期：2010.12.17

  Herein, an efficient Lewis acid catalyzed protocol for the homo-Nazarov cyclizations of alkenyl cyclopropyl ketones is reported. Alkenes bearing β-hydrogens (or silyl groups) provide 1.5:1 mixtures of methylene cyclohexenols and cyclohexenones. When no β-hydrogens (or silyl groups) are present, only cyclohexenones are observed. Products are rapidly formed in good to high yields (up to 93%) under mild

  在此，报道了用于烯基环丙基酮的均一纳扎罗夫环化的有效路易斯酸催化方案。带有β-氢（或甲硅烷基）的烯烃提供亚甲基环己醇和环己烯酮的1.5：1混合物。当不存在β-氢（或甲硅烷基）时，仅观察到环己烯酮。在温和的条件下，产品以高至高收率（高达93％）的速度迅速形成，并且很容易衍生化。