formylmethyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: formylmethyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate
• 英文别名: 2-oxoethyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: ASNKJQTXDUVSDK-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-2-(6-甲氧基-2-萘基)丙酰氯 在 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 formylmethyl (S)-2-(6-methoxynaphthalen-2-yl)propanoate
  参考文献：
  名称：

  Stereodifferentiation in the Photochemical Cycloreversion of Diastereomeric Methoxynaphthalene−Oxetane Dyads

  摘要：

  Intramolecular PET cycloreversion of oxetanes 1 and 2 has been achieved in acetonitrile and chloroform as solvents. Interestingly, a higher photoreactivity has been found in acetonitrile, while a significant stereodifferentiation has been found in chloroform. This stereodifferentiation can be attributed to the folded conformation which predominates in 2, with the naphthalene ring directed toward the oxetane region, allowing for the intramolecular electron transfer. Accordingly, intramolecular fluorescence quenching is also more efficient in acetonitrile, whereas stereodifferentiation is markedly higher in chloroform. Thus, a good correlation can be established between the results from steady-state irradiations and fluorescence measurements.

  DOI：

  10.1021/jo048708+

文献信息

• Stereodifferentiation in the Photochemical Cycloreversion of Diastereomeric Methoxynaphthalene−Oxetane Dyads
  作者：Raúl Pérez-Ruiz、Salvador Gil、Miguel A. Miranda

  DOI：10.1021/jo048708+

  日期：2005.2.1

  Intramolecular PET cycloreversion of oxetanes 1 and 2 has been achieved in acetonitrile and chloroform as solvents. Interestingly, a higher photoreactivity has been found in acetonitrile, while a significant stereodifferentiation has been found in chloroform. This stereodifferentiation can be attributed to the folded conformation which predominates in 2, with the naphthalene ring directed toward the oxetane region, allowing for the intramolecular electron transfer. Accordingly, intramolecular fluorescence quenching is also more efficient in acetonitrile, whereas stereodifferentiation is markedly higher in chloroform. Thus, a good correlation can be established between the results from steady-state irradiations and fluorescence measurements.