1-iodo-7α,8α-[N-(4-bromophenyl)-2,5-dioxopyrrolidino][3,4-h]-6,14-endo-etheno-6,7,8,14-tetrahydrothebaine | 1416672-95-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 1-iodo-7α,8α-[N-(4-bromophenyl)-2,5-dioxopyrrolidino][3,4-h]-6,14-endo-etheno-6,7,8,14-tetrahydrothebaine
• CAS: 1416672-95-1
• 化学式: C₂₉H₂₆BrIN₂O₅
• 分子量: 689.344
• InChiKey: FMFZZMBYJUDXKP-WIAZSDGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  38.0
• 可旋转键数：
  3.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.31
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-iodo-7α,8α-[N-(4-bromophenyl)-2,5-dioxopyrrolidino][3,4-h]-6,14-endo-etheno-6,7,8,14-tetrahydrothebaine 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三苯基膦 作用下， 以 苯 为溶剂， 以80%的产率得到1-(2-trimethylsilylethynyl)-7α,8α-[N-(4-bromophenyl)-2,5-dioxopyrrolidino][3,4-h]-6,14-endo-etheno-6,7,8,14-tetrahydrothebaine
  参考文献：
  名称：

  Synthetic transformations of isoquinoline alkaloids. Synthesis of N′-substituted 1-alkynyl-7α,8α-(2,5-dioxopyrrolidino)-[3,4-h]-6,14-endo-ethenotetrahydrothebaines and their transformations

  摘要：

  The iodination of N'-substituted (2,5-dioxopyrrolidino)[3,4-h]-6,14-endo-ethenotetrahydrothebaines with N-iodosuccinimide in trifluoroacetic acid afforded depending on the excess of the reagent either 1-iodo- or 1,2-diiodoendo-ethenotetrahydrothebaines. The Sonogashira reaction of 1-iodo-6,14-endo-ethenotetrahydrothebaines with trimethylsilylacetylene led to the formation of N'-substituted 1-(trimethylsilylethynyl)-(2,5-dioxopyrrolidino)-[3,4-h]-6,14-endo-ethenotetrahydrothebaines whose desilylation cleanly furnished the corresponding 1-ethynylendo-ethenotetrahydrothebaines. The Mannich reaction of the acetylene derivatives of tetrahydrothebaine with amines and formaldehyde catalyzed by compounds of Cu(I) provided 1-[3-(morpholin-4-yl)propynyl]-, 1-[3-(4-methylpiperazin-1-yl)propynyl]-, and 1-[3-(4-tert-butoxycarbonylpiperazin-1-yl)propynyl]-(2,5-dioxopyrrolidino)[3,4-h]-6,14-endo-ethenotetrahydrothebaines.

  DOI：

  10.1134/s1070428012110103
• 作为产物：
  描述：

  (1S,2S,6R,14R,15R,16S,20R)-18-(4-bromophenyl)-11,15-dimethoxy-5-methyl-13-oxa-5,18-diazaheptacyclo[13.5.2.12,8.01,6.02,14.016,20.012,23]tricosa-8(23),9,11,21-tetraene-17,19-dione 在 N-碘代丁二酰亚胺 、 三氟乙酸 作用下， 反应 2.0h， 以98%的产率得到1-iodo-7α,8α-[N-(4-bromophenyl)-2,5-dioxopyrrolidino][3,4-h]-6,14-endo-etheno-6,7,8,14-tetrahydrothebaine
  参考文献：
  名称：

  Synthetic transformations of isoquinoline alkaloids. Synthesis of N′-substituted 1-alkynyl-7α,8α-(2,5-dioxopyrrolidino)-[3,4-h]-6,14-endo-ethenotetrahydrothebaines and their transformations

  摘要：

  The iodination of N'-substituted (2,5-dioxopyrrolidino)[3,4-h]-6,14-endo-ethenotetrahydrothebaines with N-iodosuccinimide in trifluoroacetic acid afforded depending on the excess of the reagent either 1-iodo- or 1,2-diiodoendo-ethenotetrahydrothebaines. The Sonogashira reaction of 1-iodo-6,14-endo-ethenotetrahydrothebaines with trimethylsilylacetylene led to the formation of N'-substituted 1-(trimethylsilylethynyl)-(2,5-dioxopyrrolidino)-[3,4-h]-6,14-endo-ethenotetrahydrothebaines whose desilylation cleanly furnished the corresponding 1-ethynylendo-ethenotetrahydrothebaines. The Mannich reaction of the acetylene derivatives of tetrahydrothebaine with amines and formaldehyde catalyzed by compounds of Cu(I) provided 1-[3-(morpholin-4-yl)propynyl]-, 1-[3-(4-methylpiperazin-1-yl)propynyl]-, and 1-[3-(4-tert-butoxycarbonylpiperazin-1-yl)propynyl]-(2,5-dioxopyrrolidino)[3,4-h]-6,14-endo-ethenotetrahydrothebaines.

  DOI：

  10.1134/s1070428012110103