(Z)-(2S,4R)-6-Bromo-2-(2,4-dimethoxy-3-methyl-phenyl)-4-methyl-hex-5-enoic acid methyl ester | 627077-44-5

• 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: (Z)-(2S,4R)-6-Bromo-2-(2,4-dimethoxy-3-methyl-phenyl)-4-methyl-hex-5-enoic acid methyl ester
• 英文别名: methyl (Z,2S,4R)-6-bromo-2-(2,4-dimethoxy-3-methylphenyl)-4-methylhex-5-enoate
• CAS: 627077-44-5
• 化学式: C₁₇H₂₃BrO₄
• 分子量: 371.271
• InChiKey: WNKGBRHAPDPZAN-PKZQLUFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-(2S,4R)-6-Bromo-2-(2,4-dimethoxy-3-methyl-phenyl)-4-methyl-hex-5-enoic acid methyl ester 在 2,6-二甲基吡啶 、 salcomine 、 叔丁基锂 、 氧气 、 二异丁基氢化铝 、 三苯基膦 、 lithium iodide 、 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 (1R,3R,3aR,6R,6aR,10aS)-8-Hydroxy-3,6,9-trimethyl-1-(2-methyl-propenyl)-1,2,3,3a,6,6a-hexahydro-cyclopenta[d]naphthalene-7,10-dione
  参考文献：
  名称：

  A General Strategy to Elisabethane Diterpenes:  Stereocontrolled Synthesis of Elisapterosin B via Oxidative Cyclization of an Elisabethin Precursor

  摘要：

  Described is an efficient synthesis of the complex bioactive natural product, elisapterosin B, a potent in vitro inhibitor of Mycobacterium tuberculosis H37Rb. The synthesis elisapterosin B, prepared in its enantiomeric form, proceeds by a highly stereocontrolled sequence commencing with a simple glutamic acid derived compound. Pivotal steps in the sequence include (a) a pinacol-type ketal rearrangement to transfer chirality, (b) an IMDA reaction of an E,Z-diene to construct the elisabethin skeleton, and (c) a biosynthesis-inspired oxidative cyclization of the elisabethin precursor to elisapterosin B.

  DOI：

  10.1021/ja035898h
• 作为产物：
  描述：

  Methanesulfonic acid (1S,3R)-1-[(2,4-dimethoxy-3-methyl-phenyl)-dimethoxy-methyl]-3-methyl-pent-4-ynyl ester 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 、 calcium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 (Z)-(2S,4R)-6-Bromo-2-(2,4-dimethoxy-3-methyl-phenyl)-4-methyl-hex-5-enoic acid methyl ester
  参考文献：
  名称：

  A General Strategy to Elisabethane Diterpenes:  Stereocontrolled Synthesis of Elisapterosin B via Oxidative Cyclization of an Elisabethin Precursor

  摘要：

  Described is an efficient synthesis of the complex bioactive natural product, elisapterosin B, a potent in vitro inhibitor of Mycobacterium tuberculosis H37Rb. The synthesis elisapterosin B, prepared in its enantiomeric form, proceeds by a highly stereocontrolled sequence commencing with a simple glutamic acid derived compound. Pivotal steps in the sequence include (a) a pinacol-type ketal rearrangement to transfer chirality, (b) an IMDA reaction of an E,Z-diene to construct the elisabethin skeleton, and (c) a biosynthesis-inspired oxidative cyclization of the elisabethin precursor to elisapterosin B.

  DOI：

  10.1021/ja035898h

文献信息

• A General Strategy to Elisabethane Diterpenes:  Stereocontrolled Synthesis of Elisapterosin B via Oxidative Cyclization of an Elisabethin Precursor
  作者：Nobuaki Waizumi、Ana R. Stankovic、Viresh H. Rawal

  DOI：10.1021/ja035898h

  日期：2003.10.1

  Described is an efficient synthesis of the complex bioactive natural product, elisapterosin B, a potent in vitro inhibitor of Mycobacterium tuberculosis H37Rb. The synthesis elisapterosin B, prepared in its enantiomeric form, proceeds by a highly stereocontrolled sequence commencing with a simple glutamic acid derived compound. Pivotal steps in the sequence include (a) a pinacol-type ketal rearrangement to transfer chirality, (b) an IMDA reaction of an E,Z-diene to construct the elisabethin skeleton, and (c) a biosynthesis-inspired oxidative cyclization of the elisabethin precursor to elisapterosin B.