2-(diphenyl(3-phenylpropoxy)methyl)-4-methoxyphenol | 1310450-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 2-(diphenyl(3-phenylpropoxy)methyl)-4-methoxyphenol
• 英文别名: 2-[Diphenyl(3-phenylpropoxy)methyl]-4-methoxyphenol
• CAS: 1310450-09-9
• 化学式: C₂₉H₂₈O₃
• 分子量: 424.54
• InChiKey: PWIWKSMIURVUJL-UHFFFAOYSA-N

物化性质

• 熔点：
  91.5-91.8 °C
• 沸点：
  566.7±50.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(diphenyl(3-phenylpropoxy)methyl)-4-methoxyphenol 在 sodium hydride 作用下， 以 四氢呋喃 、 water-d2 、 氘代乙腈 为溶剂， 反应 0.17h， 生成 3-苯丙醇
  参考文献：
  名称：

  Development of Trityl-Based Photolabile Hydroxyl Protecting Groups

  摘要：

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.

  DOI：

  10.1021/jo200692c
• 作为产物：
  描述：

  3,3'-((4-methoxyphenyl)(3-phenylpropoxy)methylene)bis(N,N-dimethylaniline) 以 water-d2 、 二氯甲烷 、 氘代乙腈 为溶剂， 反应 0.12h， 生成 2-(diphenyl(3-phenylpropoxy)methyl)-4-methoxyphenol
  参考文献：
  名称：

  Development of Trityl-Based Photolabile Hydroxyl Protecting Groups

  摘要：

  A series of trityl-based photolabile hydroxyl protecting groups have been examined. These PPGs evolve from the traditional acid-labile trityl protecting group with proper electron-donating substituents. Structure-reactivity relationships have been explored. A m-dimethylamino group is crucial to achieve high photochemical deprotection efficiency. The o-hydroxyl group in 8 greatly improves the yield of the photochemical deprotection reaction, compared with the corresponding o-methoxyl-substituted counterpart 7. However, comparison between the photoreactions of 9 and 11 does not show similar structural relevance. The PPG in ether I (i.e., DMATr group) is structurally simple and easy to prepare and install. Its deprotection can be successfully carried out with irradiation of sunlight without requirement of photochemical devices.

  DOI：

  10.1021/jo200692c

文献信息

• Oxidation with a Photolabile Carbonyl Protecting Group
  作者：Haishen Yang、Feng Mu、Pengfei Wang

  DOI：10.1021/jo201671v

  日期：2011.11.4

  Secondary alcohols are oxidized to the corresponding ketones. Moreover, the photolabile protecting group (PPG) also oxidizes ethers and esters. The oxidation is presumably via hydride abstraction by the tritylium ion generated from 1 under acidic conditions. However, the mechanisms for primary alcohols and secondary alcohols are slightly different.

  已经开发出一种新的氧化方法，该方法利用了坚固的光不稳定的羰基保护基试剂（1）作为氧化剂。与现有方法不同，该方法将伯醇氧化为光敏乙缩醛（例如3），为受保护的醛提供了另一种独特的方法。因此，第一次在一个反应​​中实现了氧化和保护。仲醇被氧化成相应的酮。此外，光不稳定的保护基团（PPG）还会氧化醚和酯。氧化大概是通过在酸性条件下从1生成的三苯甲基离子通过氢化物提取来实现的。但是，伯醇和仲醇的机理略有不同。