(E)-1-cyclohexenyl-2-methylbut-2-en-1-one | 1428319-29-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1-cyclohexenyl-2-methylbut-2-en-1-one
• 英文别名: (E)-1-(cyclohexen-1-yl)-2-methylbut-2-en-1-one
• CAS: 1428319-29-2
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: AADKZDVEEKEEEM-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  (E)-1-cyclohexenyl-2-methylbut-2-en-1-one 在 C₄₆H₅₆CrN₂O₂⁽¹⁺⁾*F₆Sb^(1-) 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(2S,3R,3aR)-2,3-dimethyl-2,3,3a,4,5,6-hexahydro-1H-inden-1-one
  参考文献：
  名称：

  Salen Promoted Enantioselective Nazarov Cyclizations of Activated and Unactivated Dienones

  摘要：

  A novel class of chiral 5,5'-di(2,4,6-trialkyl)-aryl salen-metal complexes have been developed and shown to catalyze highly enantioselective Nazarov cyclization reactions, giving rise to cyclopentenoids in 90:10-98:2 er. Significantly, the catalysts also promote, for the first time, highly enantioselective Nazarov reactions of "unactivated" dienones, producing hydrindenone products having in place three contiguous chiral centers.

  DOI：

  10.1021/ja401908m
• 作为产物：
  描述：

  1-溴-1-环己烯E 在 吡啶 、 叔丁基锂 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 二氯甲烷 、 正戊烷 为溶剂， 反应 2.25h， 生成 (E)-1-cyclohexenyl-2-methylbut-2-en-1-one
  参考文献：
  名称：

  Salen Promoted Enantioselective Nazarov Cyclizations of Activated and Unactivated Dienones

  摘要：

  A novel class of chiral 5,5'-di(2,4,6-trialkyl)-aryl salen-metal complexes have been developed and shown to catalyze highly enantioselective Nazarov cyclization reactions, giving rise to cyclopentenoids in 90:10-98:2 er. Significantly, the catalysts also promote, for the first time, highly enantioselective Nazarov reactions of "unactivated" dienones, producing hydrindenone products having in place three contiguous chiral centers.

  DOI：

  10.1021/ja401908m

文献信息

• Nazarov Cyclization of Divinyl and Arylvinyl Epoxides: Application in the Synthesis of Resveratrol-Based Natural Products
  作者：Gangarajula Sudhakar、Kovela Satish

  DOI：10.1002/chem.201500362

  日期：2015.4.20

  New variation in the Nazarov cyclization has been developed by preparing divinyl and arylvinyl epoxides as pentadienyl cation precursors for the first time. Highly substituted cyclopentadienes, hydrindienes, and indenes were synthesized to demonstrate the compatibility of this reaction with substrates bearing a variety of substitutions and having different types of epoxides. Application of this method

  通过首次将二乙烯基和芳基乙烯基环氧化物制备为戊二烯基阳离子前体，已开发出Nazarov环化的新变化形式。合成了高度取代的环戊二烯，羟基和茚基，以证明该反应与带有各种取代基和环氧化物类型不同的底物的相容性。还证明了该方法在合成以白藜芦醇为基础的天然产物中的应用。
• Nazarov cyclization of dienylaziridines: synthesis of cyclopentadienyl/hydrinedienyl/indenyl glycines
  作者：Gangarajula Sudhakar、Karla Janardhan Reddy、Jagadesh Babu Nanubolu

  DOI：10.1039/c5ob01219h

  日期：——

  Cyclopentadienyl, hydrinedienyl, and indenyl glycines were synthesized by the Nazarov cyclization of dienylaziridines for the first time. Several substrates were synthesized to demonstrate the compatibility of this reaction. Asymmetric synthesis of these amino acids was also developed to show the additional scope of this method.

  环戊二烯基甘氨酸、氢化二烯基甘氨酸和茚基甘氨酸首次通过二烯基环氧丙烷的纳扎罗夫环化反应合成。合成了几种底物以证明此反应的兼容性。还开发了这些氨基酸的不对称合成，以展示该方法的附加范围。