(1R,2S,6S,7R,8R,12Z)-13-methyl-6-prop-1-en-2-yl-15-oxatricyclo[6.6.1.02,7]pentadec-12-ene-3,9-dione | 1254294-96-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (1R,2S,6S,7R,8R,12Z)-13-methyl-6-prop-1-en-2-yl-15-oxatricyclo[6.6.1.02,7]pentadec-12-ene-3,9-dione
• CAS: 1254294-96-6
• 化学式: C₁₈H₂₄O₃
• 分子量: 288.387
• InChiKey: HYGGRUAZXJAGJX-CGNOVHKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,6S,7R,8R,12Z)-13-methyl-6-prop-1-en-2-yl-15-oxatricyclo[6.6.1.02,7]pentadec-12-ene-3,9-dione 、 甲基锂 以 四氢呋喃 、 乙醚 为溶剂， 以99%的产率得到(1R,2S,3S,6S,7R,8R,9R,12Z)-3,9,13-trimethyl-6-prop-1-en-2-yl-15-oxatricyclo[6.6.1.02,7]pentadec-12-ene-3,9-diol
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of Briarellin J

  摘要：

  The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.

  DOI：

  10.1021/ol102169w
• 作为产物：
  描述：

  (1R,2S,6S,7R,8R,9R,12Z)-9-hydroxy-13-methyl-6-prop-1-en-2-yl-15-oxatricyclo[6.6.1.02,7]pentadec-12-en-3-one 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以99%的产率得到(1R,2S,6S,7R,8R,12Z)-13-methyl-6-prop-1-en-2-yl-15-oxatricyclo[6.6.1.02,7]pentadec-12-ene-3,9-dione
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of Briarellin J

  摘要：

  The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.

  DOI：

  10.1021/ol102169w

文献信息

• Total Synthesis of the Proposed Structure of Briarellin J
  作者：Michael T. Crimmins、Mark C. Mans、Abimael D. Rodríguez

  DOI：10.1021/ol102169w

  日期：2010.11.5

  The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.