2-[[Tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-6-methoxybenzaldehyde | 388570-72-7

• 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(dimethyl)silyl]oxymethyl]-4-hydroxy-6-methoxybenzaldehyde
• CAS: 388570-72-7
• 化学式: C₁₅H₂₄O₄Si
• 分子量: 296.439
• InChiKey: DKXFPSGWHVIYFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  394.0±37.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  1,2-乙二硫醇 、 2-[[Tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-6-methoxybenzaldehyde 在 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 以14%的产率得到4-[1,3]dithiolan-2-yl-3-hydroxymethyl-5-methoxy-phenol
  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-butyldimethylsilyloxy)-2-butyn-1-ol 在 戴斯-马丁氧化剂 作用下， 以 甲苯 为溶剂， 生成 2-[[Tert-butyl(dimethyl)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