2-[Tert-butyl(dimethyl)silyl]oxy-3,4-bis(phenylmethoxy)benzaldehyde | 400008-17-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[Tert-butyl(dimethyl)silyl]oxy-3,4-bis(phenylmethoxy)benzaldehyde
• CAS: 400008-17-5
• 化学式: C₂₇H₃₂O₄Si
• 分子量: 448.634
• InChiKey: SKVBMPPEMRSAOP-UHFFFAOYSA-N

物化性质

• 沸点：
  545.3±50.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-[Tert-butyl(dimethyl)silyl]oxy-3,4-bis(phenylmethoxy)benzaldehyde 在 palladium on activated charcoal manganese(IV) oxide 、 氢氧化钾 、 正丁基锂 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 11.75h， 生成 3,5,6-tris(1,1-dimethylallyloxy)-1-methoxyxanthen-9-one
  参考文献：
  名称：

  “Biomimetic” Cascade Reactions in Organic Synthesis: Construction of 4-Oxatricyclo[4.3.1.0]decan-2-one Systems and Total Synthesis of 1-O-Methylforbesione via Tandem Claisen Rearrangement/Diels-Alder Reactions

  摘要：

  A further demonstration of the value of "biomimetically" inspired synthetic strategies toward natural products is provided by the title reactions that were developed for the construction of 4-oxatricyclo[4.3.1.0]decan-2-one systems from prochiral aromatic precursors. This biomimetic cascade was applied to the synthesis of 1-O-methylforbesione (2) from the prenylated xanthone 1 in one pot.

  DOI：

  10.1002/1521-3773(20011119)40:22<4264::aid-anie4264>3.0.co;2-1
• 作为产物：
  描述：

  2,3,4-三羟基苯甲醛 在 potassium carbonate 、 magnesium bromide 作用下， 以 丙酮 为溶剂， 生成 2-[Tert-butyl(dimethyl)silyl]oxy-3,4-bis(phenylmethoxy)benzaldehyde
  参考文献：
  名称：

  “Biomimetic” Cascade Reactions in Organic Synthesis: Construction of 4-Oxatricyclo[4.3.1.0]decan-2-one Systems and Total Synthesis of 1-O-Methylforbesione via Tandem Claisen Rearrangement/Diels-Alder Reactions

  摘要：

  A further demonstration of the value of "biomimetically" inspired synthetic strategies toward natural products is provided by the title reactions that were developed for the construction of 4-oxatricyclo[4.3.1.0]decan-2-one systems from prochiral aromatic precursors. This biomimetic cascade was applied to the synthesis of 1-O-methylforbesione (2) from the prenylated xanthone 1 in one pot.

  DOI：

  10.1002/1521-3773(20011119)40:22<4264::aid-anie4264>3.0.co;2-1

文献信息

• Biomimetic Total Synthesis of Gambogin and Rate Acceleration of Pericyclic Reactions in Aqueous Media
  作者：K. C. Nicolaou、Hao Xu、Markus Wartmann

  DOI：10.1002/anie.200462211

  日期：2005.1.21
• “Biomimetic” Cascade Reactions in Organic Synthesis: Construction of 4-Oxatricyclo[4.3.1.0]decan-2-one Systems and Total Synthesis of 1-O-Methylforbesione via Tandem Claisen Rearrangement/Diels-Alder Reactions
  作者：K. C. Nicolaou、Jim Li

  DOI：10.1002/1521-3773(20011119)40:22<4264::aid-anie4264>3.0.co;2-1

  日期：2001.11.19

  A further demonstration of the value of "biomimetically" inspired synthetic strategies toward natural products is provided by the title reactions that were developed for the construction of 4-oxatricyclo[4.3.1.0]decan-2-one systems from prochiral aromatic precursors. This biomimetic cascade was applied to the synthesis of 1-O-methylforbesione (2) from the prenylated xanthone 1 in one pot.