4-[[Tert-butyl(dimethyl)silyl]oxymethyl]naphthalene-1-carbaldehyde | 1425052-06-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[[Tert-butyl(dimethyl)silyl]oxymethyl]naphthalene-1-carbaldehyde
• 英文别名: 4-[[tert-butyl(dimethyl)silyl]oxymethyl]naphthalene-1-carbaldehyde
• CAS: 1425052-06-7
• 化学式: C₁₈H₂₄O₂Si
• 分子量: 300.473
• InChiKey: YZEVLXNAEWVJPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[[Tert-butyl(dimethyl)silyl]oxymethyl]naphthalene-1-carbaldehyde 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 以98%的产率得到4-hydroxymethyl-1-naphthaldehyde
  参考文献：
  名称：

  Effects of Electronics, Aromaticity, and Solvent Polarity on the Rate of Azaquinone–Methide-Mediated Depolymerization of Aromatic Carbamate Oligomers

  摘要：

  This paper uses physical-organic studies on well-defined oligomers to establish design principles for creating aromatic poly(carbamates) that depolymerize from head-to-tail in low dielectric constant environments when exposed to specific applied signals. We show that either increasing electron density or decreasing the aromaticity of aromatic repeating units in poly(carbamates) increase the overall depolymerization rate. For example, a methoxybenzene-based repeating unit provides depolymerization rates that are 143X faster than oligomers that contain a benzene-based repeating unit. Furthermore, the rate of depolymerization in the methoxybenzene-based system is tolerant to low dielectric environments, whereas the benzene-based oligomers are not.

  DOI：

  10.1021/jo400105m
• 作为产物：
  描述：

  1-溴-4-(溴甲基)萘 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 calcium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 29.58h， 生成 4-[[Tert-butyl(dimethyl)silyl]oxymethyl]naphthalene-1-carbaldehyde
  参考文献：
  名称：

  Effects of Electronics, Aromaticity, and Solvent Polarity on the Rate of Azaquinone–Methide-Mediated Depolymerization of Aromatic Carbamate Oligomers

  摘要：

  This paper uses physical-organic studies on well-defined oligomers to establish design principles for creating aromatic poly(carbamates) that depolymerize from head-to-tail in low dielectric constant environments when exposed to specific applied signals. We show that either increasing electron density or decreasing the aromaticity of aromatic repeating units in poly(carbamates) increase the overall depolymerization rate. For example, a methoxybenzene-based repeating unit provides depolymerization rates that are 143X faster than oligomers that contain a benzene-based repeating unit. Furthermore, the rate of depolymerization in the methoxybenzene-based system is tolerant to low dielectric environments, whereas the benzene-based oligomers are not.

  DOI：

  10.1021/jo400105m

文献信息

• Effects of Electronics, Aromaticity, and Solvent Polarity on the Rate of Azaquinone–Methide-Mediated Depolymerization of Aromatic Carbamate Oligomers
  作者：Jessica S. Robbins、Kyle M. Schmid、Scott T. Phillips

  DOI：10.1021/jo400105m

  日期：2013.4.5

  This paper uses physical-organic studies on well-defined oligomers to establish design principles for creating aromatic poly(carbamates) that depolymerize from head-to-tail in low dielectric constant environments when exposed to specific applied signals. We show that either increasing electron density or decreasing the aromaticity of aromatic repeating units in poly(carbamates) increase the overall depolymerization rate. For example, a methoxybenzene-based repeating unit provides depolymerization rates that are 143X faster than oligomers that contain a benzene-based repeating unit. Furthermore, the rate of depolymerization in the methoxybenzene-based system is tolerant to low dielectric environments, whereas the benzene-based oligomers are not.