Methyl 3-[(2-ethenyl-4,5-dimethoxyphenyl)methyl]-1-methyl-2-(trifluoromethylsulfonyloxy)cyclohex-2-ene-1-carboxylate | 849097-94-5

• 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: Methyl 3-[(2-ethenyl-4,5-dimethoxyphenyl)methyl]-1-methyl-2-(trifluoromethylsulfonyloxy)cyclohex-2-ene-1-carboxylate
• CAS: 849097-94-5
• 化学式: C₂₁H₂₅F₃O₇S
• 分子量: 478.487
• InChiKey: IKQKGKRTKNUNBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Methyl 3-[(2-ethenyl-4,5-dimethoxyphenyl)methyl]-1-methyl-2-(trifluoromethylsulfonyloxy)cyclohex-2-ene-1-carboxylate 在 双(乙腈)氯化钯(II) 三丁基乙烯基锡 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到methyl 6,7-dimethoxy-1,9-dimethyl-3,4-dihydro-2H-anthracene-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-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-1-methyl-2-oxo-cyclohexanecarboxylic acid methyl ester 在 palladium on activated charcoal 、 四(三苯基膦)钯 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 、 乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 87.5h， 生成 Methyl 3-[(2-ethenyl-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