(1R,6S,7S,8R,10R,15S,16S,17R)-6,15-Dimethoxy-7,16-dimethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-dione

• 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: (1R,6S,7S,8R,10R,15S,16S,17R)-6,15-Dimethoxy-7,16-dimethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-dione
• 英文别名: (1R,6S,7S,8R,10R,15S,16S,17R)-6,15-dimethoxy-7,16-dimethyl-4,9,13,18-tetraoxatricyclo[15.1.0.08,10]octadecane-3,12-dione
• 化学式: C₁₈H₂₈O₈
• 分子量: 372.416
• InChiKey: UAAQKNXMBUOZNK-ONYILYPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  96.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1R,6S,7S,8R,10R,15S,16S,17R)-6,15-Dimethoxy-7,16-dimethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以90%的产率得到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：

  (6R,14R)-dimethyl-(7S,15S)-dimethoxy-1,9-dioxacyclohexadeca-(4E,12E)-diene-2,10-dione 在 间氯过氧苯甲酸 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以62%的产率得到(1R,6S,7S,8R,10R,15S,16S,17R)-6,15-Dimethoxy-7,16-dimethyl-4,9,13,18-tetraoxa-tricyclo[15.1.0.0^8,10]octadecane-3,12-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

文献信息

• Stereochemical Diversity through Cyclodimerization:  Synthesis of Polyketide-like Macrodiolides
  作者：Qibin Su、Aaron B. Beeler、Emil Lobkovsky、John A. Porco,、James S. Panek

  DOI：10.1021/ol034608z

  日期：2003.6.1

  [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.