(1R,2R,3S,4S,7S,8S,11R,14Z,17R)-4-hydroxy-4,8,11,15-tetramethyl-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadec-14-en-9-one | 1254295-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (1R,2R,3S,4S,7S,8S,11R,14Z,17R)-4-hydroxy-4,8,11,15-tetramethyl-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadec-14-en-9-one
• CAS: 1254295-07-2
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: GNHXXGXSNVJBDM-JNVDXKKLSA-N

物化性质

• 沸点：
  490.4±45.0 °C(predicted)
• 密度：
  1.106±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸异丙烯酯 、 (1R,2R,3S,4S,7S,8S,11R,14Z,17R)-4-hydroxy-4,8,11,15-tetramethyl-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadec-14-en-9-one 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 8.0h， 以64%的产率得到briarellin J
  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：

  briarellin J 在 二异丁基氢化铝 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以43%的产率得到(1R,2R,3S,4S,7S,8S,11R,14Z,17R)-4-hydroxy-4,8,11,15-tetramethyl-10,18-dioxatetracyclo[9.7.0.02,7.03,17]octadec-14-en-9-one
  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