5-(benzyloxy)-2-chlorobicyclo[4.2.0]octa-1,3,5-trien-7-one | 1612240-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(benzyloxy)-2-chlorobicyclo[4.2.0]octa-1,3,5-trien-7-one
• 英文别名: 2-Chloro-5-phenylmethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one；2-chloro-5-phenylmethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one
• CAS: 1612240-24-0
• 化学式: C₁₅H₁₁ClO₂
• 分子量: 258.704
• InChiKey: AUZCZRYZOLHKNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  5-(benzyloxy)-2-chlorobicyclo[4.2.0]octa-1,3,5-trien-7-one 在 盐酸 、 palladium hydroxide, 20 wt% on carbon 、 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 以89%的产率得到
  参考文献：
  名称：

  Enantioselective Rh-Catalyzed Carboacylation of C═N Bonds via C–C Activation of Benzocyclobutenones

  摘要：

  Herein we describe the first enantioselective Rh catalyzed carboacylation of mimes (imines) via C-C activation. In this transformation, the benzocyclobutenone C1-C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh-C bonds add across a C=N bond, which provides a unique approach to access chiral lactams. A range of polycydic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles.

  DOI：

  10.1021/jacs.5b11120
• 作为产物：
  描述：

  3-溴-4-氯苯酚 在 2,2,6,6-tetramethylpiperidinyl-lithium 、 potassium carbonate 、 pyridinium chlorochromate 、 potassium iodide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 6.0h， 生成 5-(benzyloxy)-2-chlorobicyclo[4.2.0]octa-1,3,5-trien-7-one
  参考文献：
  名称：

  Enantioselective Rh-Catalyzed Carboacylation of C═N Bonds via C–C Activation of Benzocyclobutenones

  摘要：

  Herein we describe the first enantioselective Rh catalyzed carboacylation of mimes (imines) via C-C activation. In this transformation, the benzocyclobutenone C1-C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh-C bonds add across a C=N bond, which provides a unique approach to access chiral lactams. A range of polycydic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles.

  DOI：

  10.1021/jacs.5b11120

文献信息

• Concise synthesis of functionalized benzocyclobutenones
  作者：P.-H. Chen、Nikolas A. Savage、Guangbin Dong

  DOI：10.1016/j.tet.2014.03.080

  日期：2014.7

  to access functionalized benzocyclobutenones from 3-halophenol derivatives is described. This modified synthesis employs a [2+2] cycloaddition between benzynes generated from dehydrohalogenation of aryl halides using LiTMP and acetaldehyde enolate generated from n-BuLi and THF, followed by oxidation of the benzocyclobutenol intermediates to provide benzocyclobutenones. The [2+2] reaction can be run on

  描述了从 3-卤代苯酚衍生物中获取功能化苯并环丁烯酮的简洁方法。这种改进的合成采用 [2+2] 环加成在芳基卤化物脱卤化氢产生的苄与n- BuLi 和 THF产生的乙醛烯醇化物之间进行 [2+2] 环加成，然后氧化苯并环丁烯醇中间体以提供苯并环丁烯酮。[2+2] 反应可以以 10-g 的规模进行，并提高产率。可以容忍许多官能团，包括烯烃和炔烃。还证明了苄与烯酮甲硅烷基缩醛的偶联得到8-取代的苯并环丁烯酮。
• Enantioselective Rh-Catalyzed Carboacylation of C═N Bonds via C–C Activation of Benzocyclobutenones
  作者：Lin Deng、Tao Xu、Hongbo Li、Guangbin Dong

  DOI：10.1021/jacs.5b11120

  日期：2016.1.13

  Herein we describe the first enantioselective Rh catalyzed carboacylation of mimes (imines) via C-C activation. In this transformation, the benzocyclobutenone C1-C2 bond is selectively activated by a low valent rhodium catalyst and subsequently the resulting two Rh-C bonds add across a C=N bond, which provides a unique approach to access chiral lactams. A range of polycydic nitrogen-containing scaffolds were obtained in good yields with excellent enantioselectivity. Further derivatization of the lactam products led to a rapid entry to various novel fused heterocycles.