3-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-cyclohexanecarboxylic acid methyl ester | 849097-86-5

• 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: 3-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-cyclohexanecarboxylic acid methyl ester
• CAS: 849097-86-5
• 化学式: C₁₇H₂₀O₅
• 分子量: 304.343
• InChiKey: NBRMCWHIJWSGBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-cyclohexanecarboxylic acid methyl ester 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 氢气 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 77.5h， 生成 Methyl 3-[(2-bromo-4,5-dimethoxyphenyl)methyl]-1-methyl-2-(trifluoromethylsulfonyloxy)cyclohex-2-ene-1-carboxylate
  参考文献：
  名称：

  Intramolecular Heck reaction strategy for the synthesis of functionalised tetrahydroanthracenes: a facile formal total synthesis of the linear abietane diterpene, umbrosone

  摘要：

  Rapid annulation employing an intramolecular Heck reaction yielded the functionalised 1,1,10-trimethyl-6-methoxy-1,2,3,4-tetrahydroanthracene 4a, a key intermediate for the linear diterpenoid quinone umbrosone (1), and the related compounds 4b-d. A similar strategy was also successfully adopted for the synthesis of the 9-methyl tetrahydroanthracene ester 5 and the tetrahydrodibenzo[a,d]cycloheptene ester 6. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.021
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 2-氧环己烷羧酸甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以40%的产率得到3-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-cyclohexanecarboxylic acid methyl ester
  参考文献：
  名称：

  Intramolecular Heck reaction strategy for the synthesis of functionalised tetrahydroanthracenes: a facile formal total synthesis of the linear abietane diterpene, umbrosone

  摘要：

  Rapid annulation employing an intramolecular Heck reaction yielded the functionalised 1,1,10-trimethyl-6-methoxy-1,2,3,4-tetrahydroanthracene 4a, a key intermediate for the linear diterpenoid quinone umbrosone (1), and the related compounds 4b-d. A similar strategy was also successfully adopted for the synthesis of the 9-methyl tetrahydroanthracene ester 5 and the tetrahydrodibenzo[a,d]cycloheptene ester 6. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.01.021