(2S,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-9-[(1Z)-2-methoxybuta-1,3-dienyl]-7-methyl-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde | 1254295-15-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-9-[(1Z)-2-methoxybuta-1,3-dienyl]-7-methyl-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde
• CAS: 1254295-15-2
• 化学式: C₂₁H₃₆O₄Si
• 分子量: 380.6
• InChiKey: JCANAJKOYFXANO-SOBUUYFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-9-[(1Z)-2-methoxybuta-1,3-dienyl]-7-methyl-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde 、 1-三苯基膦-2-丙酮 以 甲苯 为溶剂， 以814 mg的产率得到1-[(1R,2S,3S,7S,8R,10Z,14R)-14-[tert-butyl(dimethyl)silyl]oxy-6-methoxy-10-methyl-15-oxatricyclo[6.6.1.02,7]pentadeca-5,10-dien-3-yl]ethanone
  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：

  [(2R,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-9-[(1Z)-2-methoxybuta-1,3-dienyl]-7-methyl-2,3,4,5,8,9-hexahydrooxonin-2-yl]methanol 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-9-[(1Z)-2-methoxybuta-1,3-dienyl]-7-methyl-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde
  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.