(+/-)-(2β,3α,3aα)-2-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3,3a-dihydro-5-methoxy-3-methyl-3a-(2-propenyl)-6(2H)-benzofuranone | 127086-32-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (+/-)-(2β,3α,3aα)-2-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3,3a-dihydro-5-methoxy-3-methyl-3a-(2-propenyl)-6(2H)-benzofuranone
• 英文别名: (2R,3R,3aS)-2-[4-[tert-butyl(dimethyl)silyl]oxy-3-methoxyphenyl]-5-methoxy-3-methyl-3a-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
• CAS: 127086-32-2；127102-26-5
• 化学式: C₂₆H₃₆O₅Si
• 分子量: 456.654
• InChiKey: YDNRZNJXIQBDBL-BQVXCWBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-(2β,3α,3aα)-2-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3,3a-dihydro-5-methoxy-3-methyl-3a-(2-propenyl)-6(2H)-benzofuranone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到Aniba neolignans
  参考文献：
  名称：

  The chemistry of a quinone methide proposed to be an intermediate in neolignan biosynthesis

  摘要：

  DOI：

  10.1021/ja00165a087
• 作为产物：
  描述：

  (+/-)-(2β,3α,3aα)-2-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3,3a-dihydro-5-methoxy-3-methyl-3a-<3-<(methylsulfonyl)oxy>propyl>-6(2H)-benzofuranone 在 sodium tetrahydroborate 、 sodium periodate 、 二苯基二硒醚 作用下， 生成 (+/-)-(2β,3α,3aα)-2-<4-<(tert-butyldimethylsilyl)oxy>-3-methoxyphenyl>-3,3a-dihydro-5-methoxy-3-methyl-3a-(2-propenyl)-6(2H)-benzofuranone
  参考文献：
  名称：

  Synthesis of neolignans via a proposed biosynthetic intermediate. Total synthesis of (.+-.)-futoenone

  摘要：

  The attempted spectroscopic observation of a quinone methide proposed to be an intermediate in the biosynthesis of neolignans is reported. The results afforded substantial indirect evidence for the formation of quinone methide 3. The synthesis of racemic bicyclo[3.2.1]octenedione 22, a natural product, is proposed to occur through a similar quinone methide intermediate. The synthesis of (+/-)-futoenone via a benzylic cation intermediate related to quinone methide 3 is reported. The results provide support for Gottlieb's proposal that several different neolignans arise from a common biosynthetic precursor. The efficient synthesis of (+/-)-futoenone and related spiro[5.5]undecanoids using a Buchi quinone ketal cycloaddition is also described.

  DOI：

  10.1021/jo00072a017

文献信息

• The chemistry of a quinone methide proposed to be an intermediate in neolignan biosynthesis
  作者：Steven R. Angle、Kenneth D. Turnbull

  DOI：10.1021/ja00165a087

  日期：1990.4
• Synthesis of neolignans via a proposed biosynthetic intermediate. Total synthesis of (.+-.)-futoenone
  作者：Steven R. Angle、Kenneth D. Turnbull

  DOI：10.1021/jo00072a017

  日期：1993.9

  The attempted spectroscopic observation of a quinone methide proposed to be an intermediate in the biosynthesis of neolignans is reported. The results afforded substantial indirect evidence for the formation of quinone methide 3. The synthesis of racemic bicyclo[3.2.1]octenedione 22, a natural product, is proposed to occur through a similar quinone methide intermediate. The synthesis of (+/-)-futoenone via a benzylic cation intermediate related to quinone methide 3 is reported. The results provide support for Gottlieb's proposal that several different neolignans arise from a common biosynthetic precursor. The efficient synthesis of (+/-)-futoenone and related spiro[5.5]undecanoids using a Buchi quinone ketal cycloaddition is also described.