(6R,14R)-dimethyl-(7S,15S)-dimethoxy-1,9-dioxacyclohexadeca-(4E,12E)-diene-2,10-dione | 864067-41-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (6R,14R)-dimethyl-(7S,15S)-dimethoxy-1,9-dioxacyclohexadeca-(4E,12E)-diene-2,10-dione
• 英文别名: (4E,6R,7S,12E,14R,15S)-7,15-dimethoxy-6,14-dimethyl-1,9-dioxacyclohexadeca-4,12-diene-2,10-dione
• CAS: 864067-41-4
• 化学式: C₁₈H₂₈O₆
• 分子量: 340.417
• InChiKey: XHGSXZXWBLXYTP-SBPSCXGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (6R,14R)-dimethyl-(7S,15S)-dimethoxy-1,9-dioxacyclohexadeca-(4E,12E)-diene-2,10-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 5.5h， 生成 6,14-dimethyl-7,15-dimethoxy-5,13-dihydroxy-1,9-dioxacyclohexadeca-(3E,11E)-diene-2,10-dione
  参考文献：
  名称：

  Stereochemical Diversity through Cyclodimerization:  Synthesis of Polyketide-like Macrodiolides

  摘要：

  [GRAPHICS]An expeditious procedure for the direct formation of stereochemically well-defined macrodiolides is described. Cyclodimerizations of enantioenriched C7 and C8 hydroxy esters 6 in the presence of catalytic amounts of distannoxane transesterification catalysts afford 14- to 22-membered macrodiolides 7-9 bearing up to six stereocenters. Additional structural diversity is introduced by further stereoselective reactions on selected macrodiolides 7a, 7g, 10a, and 11.

  DOI：

  10.1021/ol034608z
• 作为产物：
  描述：

  (E,5R,6S)-methyl 7-hydroxy-6-methoxy-5-methylhept-3-enoate 在 [Sn₂(C₄H₉)4SCN(OH)O]2 作用下， 以 氯苯 为溶剂， 反应 48.0h， 以75%的产率得到(6R,14R)-dimethyl-(7S,15S)-dimethoxy-1,9-dioxacyclohexadeca-(4E,12E)-diene-2,10-dione
  参考文献：
  名称：

  Stereochemical Diversity through Cyclodimerization:  Synthesis of Polyketide-like Macrodiolides

  摘要：

  [GRAPHICS]An expeditious procedure for the direct formation of stereochemically well-defined macrodiolides is described. Cyclodimerizations of enantioenriched C7 and C8 hydroxy esters 6 in the presence of catalytic amounts of distannoxane transesterification catalysts afford 14- to 22-membered macrodiolides 7-9 bearing up to six stereocenters. Additional structural diversity is introduced by further stereoselective reactions on selected macrodiolides 7a, 7g, 10a, and 11.

  DOI：

  10.1021/ol034608z