6-[2-benzyloxy-1,1-dimethyl-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-but-3-enyl]-4-methoxy-pyran-2-one | 570394-48-8

• 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: 6-[2-benzyloxy-1,1-dimethyl-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-but-3-enyl]-4-methoxy-pyran-2-one
• 英文别名: 4-methoxy-6-[(E,3S)-2-methyl-3-phenylmethoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-4-en-2-yl]pyran-2-one
• CAS: 570394-48-8
• 化学式: C₂₅H₃₃BO₆
• 分子量: 440.344
• InChiKey: ICNOYWJSVNCNKD-AIGDTVQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S),(8R)-2-iodo-4,6,8-trimethyl-tetradeca-2,5-diene 、 6-[2-benzyloxy-1,1-dimethyl-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-but-3-enyl]-4-methoxy-pyran-2-one 在 氢氧化钾 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以0.156 g的产率得到6-[(2S),(7S),(11R)-2-benzyloxy-1,1,5,7,9,11-hexamethylheptadeca-3,5,8-trienyl]-4-methoxy-pyran-2-one
  参考文献：
  名称：

  The Synthesis of Deoxyfusapyrone. 2. Preparation of the Bis-Trisubstituted Olefin Fragment and Its Attachment to the Pyrone Moiety

  摘要：

  A convergent and modular synthesis has been devised to construct the eight diastereoisomers of deoxyfusapyrone (1). In this paper the synthesis of the complex polyene chain is reported as is its connection to the pyrone moiety that is in the middle of the structure of the final target molecule. This route has been fully worked out for one of the isomers and will now be applied in a parallel synthesis format to make all the stereoisomers of 1.

  DOI：

  10.1021/jo034371k
• 作为产物：
  描述：

  (S)-6-(2-benzyloxy-1,1-dimethyl-but-3-ynyl)-4-methoxy-pyran-2-one 在 十二/十四烷基二甲基氧化胺 、 dimethyl sulfide borane 作用下， 以 乙二醇二甲醚 为溶剂， 反应 22.25h， 生成 6-[2-benzyloxy-1,1-dimethyl-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-but-3-enyl]-4-methoxy-pyran-2-one
  参考文献：
  名称：

  The Synthesis of Deoxyfusapyrone. 2. Preparation of the Bis-Trisubstituted Olefin Fragment and Its Attachment to the Pyrone Moiety

  摘要：

  A convergent and modular synthesis has been devised to construct the eight diastereoisomers of deoxyfusapyrone (1). In this paper the synthesis of the complex polyene chain is reported as is its connection to the pyrone moiety that is in the middle of the structure of the final target molecule. This route has been fully worked out for one of the isomers and will now be applied in a parallel synthesis format to make all the stereoisomers of 1.

  DOI：

  10.1021/jo034371k

文献信息

• The Synthesis of Deoxyfusapyrone. 2. Preparation of the Bis-Trisubstituted Olefin Fragment and Its Attachment to the Pyrone Moiety
  作者：Michael G. Organ、Junquan Wang

  DOI：10.1021/jo034371k

  日期：2003.7.1

  A convergent and modular synthesis has been devised to construct the eight diastereoisomers of deoxyfusapyrone (1). In this paper the synthesis of the complex polyene chain is reported as is its connection to the pyrone moiety that is in the middle of the structure of the final target molecule. This route has been fully worked out for one of the isomers and will now be applied in a parallel synthesis format to make all the stereoisomers of 1.