7-Benzyloxy-3-[2-(3,4-dimethoxy-phenyl)-ethyl]-1-(3-isopropoxy-4-methoxy-phenyl)-8-methoxy-4-oxo-3,4-dihydro-chromeno[3,4-b]pyrrole-2-carboxylic acid | 895632-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 7-Benzyloxy-3-[2-(3,4-dimethoxy-phenyl)-ethyl]-1-(3-isopropoxy-4-methoxy-phenyl)-8-methoxy-4-oxo-3,4-dihydro-chromeno[3,4-b]pyrrole-2-carboxylic acid
• 英文别名: 3-[2-(3,4-Dimethoxyphenyl)ethyl]-8-methoxy-1-(4-methoxy-3-propan-2-yloxyphenyl)-4-oxo-7-phenylmethoxychromeno[3,4-b]pyrrole-2-carboxylic acid；3-[2-(3,4-dimethoxyphenyl)ethyl]-8-methoxy-1-(4-methoxy-3-propan-2-yloxyphenyl)-4-oxo-7-phenylmethoxychromeno[3,4-b]pyrrole-2-carboxylic acid
• CAS: 895632-72-1
• 化学式: C₄₀H₃₉NO₁₀
• 分子量: 693.75
• InChiKey: LMCQFZCHCXBGTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  7-Benzyloxy-3-[2-(3,4-dimethoxy-phenyl)-ethyl]-1-(3-isopropoxy-4-methoxy-phenyl)-8-methoxy-4-oxo-3,4-dihydro-chromeno[3,4-b]pyrrole-2-carboxylic acid 在 palladium on activated charcoal 喹啉 、 copper(I) oxide 、 三氟化硼乙醚 、 氢气 、 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 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 33.67h， 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 盐酸 、 氢氧化钾 、 sodium carbonate 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醇 为溶剂， 反应 33.0h， 生成 7-Benzyloxy-3-[2-(3,4-dimethoxy-phenyl)-ethyl]-1-(3-isopropoxy-4-methoxy-phenyl)-8-methoxy-4-oxo-3,4-dihydro-chromeno[3,4-b]pyrrole-2-carboxylic acid
  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