2-[[Tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-6-methoxybenzaldehyde | 388570-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[[Tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-6-methoxybenzaldehyde
• CAS: 388570-73-8
• 化学式: C₂₅H₂₈O₄Si
• 分子量: 420.58
• InChiKey: OPZYTKDVSKWBGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  2-[[Tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-6-methoxybenzaldehyde 在 potassium carbonate 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 Tert-butyl-[[2-(1,3-dithiolan-2-yl)-3,5-dimethoxyphenyl]methoxy]-diphenylsilane
  参考文献：
  名称：

  4-(Trialkylsilyl)oxybut-2-ynals as dienophiles in the Diels–Alder synthesis of α-(hydroxymethyl)benzaldehydes

  摘要：

  The alpha-(hydroxymethyl)benzaldehyde derivative 2 has been synthesized by heating ynal 3 with diene 5, which produced the alpha-(silyloxymethyl)benzaldehyde 6 by a Diels-Alder retro-Diels-Alder process, followed by methylation, thioacetalization. and removal of the silyl protecting group. Decarbonylation of alpha-(silyloxymethyl)benzaldehydes des 6 and 10 takes place readily in the presence of zinc(II) chloride or para-toluenesulfonic acid. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01541-6
• 作为产物：
  描述：

  4-((tert-butyldiphenylsilyl)oxy)but-2-yn-1-ol 在 戴斯-马丁氧化剂 作用下， 以 甲苯 为溶剂， 生成 2-[[Tert-butyl(diphenyl)silyl]oxymethyl]-4-hydroxy-6-methoxybenzaldehyde
  参考文献：
  名称：

  4-(Trialkylsilyl)oxybut-2-ynals as dienophiles in the Diels–Alder synthesis of α-(hydroxymethyl)benzaldehydes

  摘要：

  The alpha-(hydroxymethyl)benzaldehyde derivative 2 has been synthesized by heating ynal 3 with diene 5, which produced the alpha-(silyloxymethyl)benzaldehyde 6 by a Diels-Alder retro-Diels-Alder process, followed by methylation, thioacetalization. and removal of the silyl protecting group. Decarbonylation of alpha-(silyloxymethyl)benzaldehydes des 6 and 10 takes place readily in the presence of zinc(II) chloride or para-toluenesulfonic acid. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01541-6

文献信息

• 4-(Trialkylsilyl)oxybut-2-ynals as dienophiles in the Diels–Alder synthesis of α-(hydroxymethyl)benzaldehydes
  作者：Christopher F Morrison、D.Jean Burnell

  DOI：10.1016/s0040-4039(01)01541-6

  日期：2001.10

  The alpha-(hydroxymethyl)benzaldehyde derivative 2 has been synthesized by heating ynal 3 with diene 5, which produced the alpha-(silyloxymethyl)benzaldehyde 6 by a Diels-Alder retro-Diels-Alder process, followed by methylation, thioacetalization. and removal of the silyl protecting group. Decarbonylation of alpha-(silyloxymethyl)benzaldehydes des 6 and 10 takes place readily in the presence of zinc(II) chloride or para-toluenesulfonic acid. (C) 2001 Elsevier Science Ltd. All rights reserved.