Ethyl <10-(Methoxyimino)phenanthren-9-ylidene>acetate | 154021-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: Ethyl <10-(Methoxyimino)phenanthren-9-ylidene>acetate
• 英文别名: ethyl 2-(10-methoxyiminophenanthren-9-ylidene)acetate
• CAS: 154021-44-0
• 化学式: C₁₉H₁₇NO₃
• 分子量: 307.349
• InChiKey: XGSPKVDDWIBYRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  47.89
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Ethyl <10-(Methoxyimino)phenanthren-9-ylidene>acetate 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 8.0h， 生成 Ethyl 10,15-dihydro-10,15-dioxotribenzoacridine-16-carboxylate
  参考文献：
  名称：

  Diels-Alder Reactions of Ethyl [10-(Methoxyimino)phenanthren-9-ylidene]acetate with Dienophiles. Synthesis of Dibenzo[f,h]quinoline and Dibenzo[a,c]acridine Derivatives

  摘要：

  [10-(Methoxyimino)phenanthren-9-ylidene]acetates 3(I,II), prepared by Wittig olefination of 10-(methoxyimino)phenanthren-9-one (1) with ylide 2, were transformed by means of a [4 + 2] cycloaddition and methanol elimination to stable spiro-compound 5. In addition, the use of compounds 3 as heterodienes in Diels-Alder reactions with various electron-deficient dienophiles 6a,b, 10a-c, and 14 led to the synthesis of nitrogen-containing polycycles 8a,b, 11a-c, 12b,c, 13b,c, and 16.

  DOI：

  10.1021/jo00084a027
• 作为产物：
  描述：

  10-(methoxyimino)phenanthren-9-one 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 72.0h， 生成 Ethyl <10-(Methoxyimino)phenanthren-9-ylidene>acetate
  参考文献：
  名称：

  Diels-Alder Reactions of Ethyl [10-(Methoxyimino)phenanthren-9-ylidene]acetate with Dienophiles. Synthesis of Dibenzo[f,h]quinoline and Dibenzo[a,c]acridine Derivatives

  摘要：

  [10-(Methoxyimino)phenanthren-9-ylidene]acetates 3(I,II), prepared by Wittig olefination of 10-(methoxyimino)phenanthren-9-one (1) with ylide 2, were transformed by means of a [4 + 2] cycloaddition and methanol elimination to stable spiro-compound 5. In addition, the use of compounds 3 as heterodienes in Diels-Alder reactions with various electron-deficient dienophiles 6a,b, 10a-c, and 14 led to the synthesis of nitrogen-containing polycycles 8a,b, 11a-c, 12b,c, 13b,c, and 16.

  DOI：

  10.1021/jo00084a027

文献信息

• Diels-Alder Reactions of Ethyl [10-(Methoxyimino)phenanthren-9-ylidene]acetate with Dienophiles. Synthesis of Dibenzo[f,h]quinoline and Dibenzo[a,c]acridine Derivatives
  作者：D. N. Nicolaides、Raed Wajih Awad、G. K. Papageorgiou、J. Stephanidou-Stephanatou

  DOI：10.1021/jo00084a027

  日期：1994.3

  [10-(Methoxyimino)phenanthren-9-ylidene]acetates 3(I,II), prepared by Wittig olefination of 10-(methoxyimino)phenanthren-9-one (1) with ylide 2, were transformed by means of a [4 + 2] cycloaddition and methanol elimination to stable spiro-compound 5. In addition, the use of compounds 3 as heterodienes in Diels-Alder reactions with various electron-deficient dienophiles 6a,b, 10a-c, and 14 led to the synthesis of nitrogen-containing polycycles 8a,b, 11a-c, 12b,c, 13b,c, and 16.