methyl (1R,9R,10R,12S,19S)-12-ethyl-10-(methoxycarbonylsulfamoyloxy)-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6-triene-10-carboxylate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 冬青素型生物碱
• 英文名称: methyl (1R,9R,10R,12S,19S)-12-ethyl-10-(methoxycarbonylsulfamoyloxy)-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6-triene-10-carboxylate
• 化学式: C₂₄H₃₃N₃O₇S
• 分子量: 507.608
• InChiKey: BGHWETICZQKZGN-UBFQBMNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (1R,9R,10R,12S,19S)-12-ethyl-10-(methoxycarbonylsulfamoyloxy)-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6-triene-10-carboxylate 在 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 (-)-3-methoxycarbonyl-Δ^3,4-1-methylaspermidospermidine 、 minovine
  参考文献：
  名称：

  Total Synthesis of Natural (−)- and ent-(+)-4-Desacetoxy-6,7-dihydrovindorosine and Natural and ent-Minovine:  Oxadiazole Tandem Intramolecular Diels−Alder/1,3-Dipolar Cycloaddition Reaction

  摘要：

  [GRAPHICS]Efficient and unusually concise total syntheses of both enantiomers of the Aspidosperma alkaloids 4-desacetoxy-6,7-dihydrovindorosine (12) and minovine (1) are detailed. A tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction of the 1,3,4-oxadiazole 8, in which three new rings, four new C-C bonds, and five stereocenters are formed, is a key step in the sequence. The availability of optically active material permitted an assessment of the enantiomeric integrity of minovine and the source of its reported unusual optical rotation.

  DOI：

  10.1021/ol050017s
• 作为产物：
  描述：

  1-甲基色胺 在 劳森试剂 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 邻二氯苯 、 甲苯 、 乙腈 为溶剂， 反应 78.66h， 生成 methyl (1R,9R,10R,12S,19S)-12-ethyl-10-(methoxycarbonylsulfamoyloxy)-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6-triene-10-carboxylate
  参考文献：
  名称：

  Total Synthesis of Natural (−)- and ent-(+)-4-Desacetoxy-6,7-dihydrovindorosine and Natural and ent-Minovine:  Oxadiazole Tandem Intramolecular Diels−Alder/1,3-Dipolar Cycloaddition Reaction

  摘要：

  [GRAPHICS]Efficient and unusually concise total syntheses of both enantiomers of the Aspidosperma alkaloids 4-desacetoxy-6,7-dihydrovindorosine (12) and minovine (1) are detailed. A tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction of the 1,3,4-oxadiazole 8, in which three new rings, four new C-C bonds, and five stereocenters are formed, is a key step in the sequence. The availability of optically active material permitted an assessment of the enantiomeric integrity of minovine and the source of its reported unusual optical rotation.

  DOI：

  10.1021/ol050017s

文献信息

• Total Synthesis of Natural (−)- and <i>e</i><i>nt</i>-(+)-4-Desacetoxy-6,7-dihydrovindorosine and Natural and <i>e</i><i>nt</i>-Minovine:  Oxadiazole Tandem Intramolecular Diels−Alder/1,3-Dipolar Cycloaddition Reaction
  作者：Zhong Qing Yuan、Hayato Ishikawa、Dale L. Boger

  DOI：10.1021/ol050017s

  日期：2005.2.1

  [GRAPHICS]Efficient and unusually concise total syntheses of both enantiomers of the Aspidosperma alkaloids 4-desacetoxy-6,7-dihydrovindorosine (12) and minovine (1) are detailed. A tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction of the 1,3,4-oxadiazole 8, in which three new rings, four new C-C bonds, and five stereocenters are formed, is a key step in the sequence. The availability of optically active material permitted an assessment of the enantiomeric integrity of minovine and the source of its reported unusual optical rotation.