1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3-(3-isopropoxy-4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester | 895632-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3-(3-isopropoxy-4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 1-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-methoxy-3-propan-2-yloxyphenyl)-4-(trifluoromethylsulfonyloxy)pyrrole-2,5-dicarboxylate；dimethyl 1-[2-(3,4-dimethoxyphenyl)ethyl]-3-(4-methoxy-3-propan-2-yloxyphenyl)-4-(trifluoromethylsulfonyloxy)pyrrole-2,5-dicarboxylate
• CAS: 895632-68-5
• 化学式: C₂₉H₃₂F₃NO₁₁S
• 分子量: 659.634
• InChiKey: URSHTOZYEFIDSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  45
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3-(3-isopropoxy-4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester 在 palladium on activated charcoal 、 四(三苯基膦)钯 喹啉 、 copper(I) oxide 、 盐酸 、 氢氧化钾 、 三氟化硼乙醚 、 氢气 、 sodium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 59.67h， 生成 3-Hydroxy-13-(3-isopropoxy-4-methoxy-phenyl)-2,10,11-trimethoxy-5-oxa-6b-aza-dibenzo[a,i]fluoren-6-one
  参考文献：
  名称：

  The first total synthesis of lamellarin α 20-sulfate, a selective inhibitor of HIV-1 integrase

  摘要：

  The first total synthesis of lamellarin alpha 20-sulfate (1), a selective inhibitor of HIV-1 integrase, has been completed. The lamellarin alpha core in which 13-OH and 20-OH were differentially protected by isopropyl and benzyl groups, respectively, was constructed by using Hinsberg-type pyrrole synthesis and Suzuki-Miyaura coupling as the key reactions. The 20-sulfate was prepared by a sequence including debenzylation of 20-OBn, 2,2,2-trichloroethylsulfation of the resulting 20-OH deprotection of 13-Oi-Pr, and final reductive cleavage of the 2,2,2-trichloroethyl ester. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.121
• 作为产物：
  描述：

  dimethyl 3,4-dihydroxy-1-[2-(3,4-dimethoxyphenyl)ethyl]pyrrole-2,5-dicarboxylate 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 7.0h， 生成 1-[2-(3,4-Dimethoxy-phenyl)-ethyl]-3-(3-isopropoxy-4-methoxy-phenyl)-4-trifluoromethanesulfonyloxy-1H-pyrrole-2,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  The first total synthesis of lamellarin α 20-sulfate, a selective inhibitor of HIV-1 integrase

  摘要：

  The first total synthesis of lamellarin alpha 20-sulfate (1), a selective inhibitor of HIV-1 integrase, has been completed. The lamellarin alpha core in which 13-OH and 20-OH were differentially protected by isopropyl and benzyl groups, respectively, was constructed by using Hinsberg-type pyrrole synthesis and Suzuki-Miyaura coupling as the key reactions. The 20-sulfate was prepared by a sequence including debenzylation of 20-OBn, 2,2,2-trichloroethylsulfation of the resulting 20-OH deprotection of 13-Oi-Pr, and final reductive cleavage of the 2,2,2-trichloroethyl ester. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.121