3-(α-naphthyl)-2,4-oxazolidinedione | 954-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(α-naphthyl)-2,4-oxazolidinedione
• 英文别名: 3-naphthalen-1-yl-oxazolidine-2,4-dione；3--oxazolidin-dion-(2,4)；3--oxazolidin-dion-(2.4)；3--oxazolidindion-(2,4)；3-(Naphthalen-1-yl)-1,3-oxazolidine-2,4-dione；3-naphthalen-1-yl-1,3-oxazolidine-2,4-dione
• CAS: 954-43-8
• 化学式: C₁₃H₉NO₃
• 分子量: 227.219
• InChiKey: GPBMVUYGUXMZFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙醇酸乙酯 、 1-Alapha-萘异氰酸酯 在 sodium 作用下， 以 甲苯 为溶剂， 反应 11.0h， 以17.3%的产率得到3-(α-naphthyl)-2,4-oxazolidinedione
  参考文献：
  名称：

  Determination of the absolute stereochemistry and the activation barriers of thermally interconvertible heterocyclic compounds bearing a naphthyl substituent

  摘要：

  The enantiotopic methyl signals of the compounds studied were resolved in the presence of the optically active chiral auxiliary (S)-(+)-2,2,2-trifluoroanthryl ethanol, [(S)-TFAE] via complex formation between (S)-TFAE and the respective compounds. Two different solvation models were proposed for both M and P conformations leading to the assignments of the H-1 NMR signals and thus absolute conformations. The solvation models proposed also explained the strong temperature dependence of the H-1 NMR signals upon cooling. The activation barriers for interconversion between the enantiomers of the compounds studied have been determined by either temperature dependent NMR or enantioresolution on a chiral sorbent via HPLC. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.09.019

文献信息

• 205. Preparation of 3-substituted oxazolid-2,4-diones by cyclisation of N-substituted N-chloroacylcarbamates
  作者：M. Pianka、D. J. Polton

  DOI：10.1039/jr9600000983

  日期：——
• US4367234A
  申请人：——

  公开号：US4367234A

  公开（公告）日：1983-01-04
• US4399296A
  申请人：——

  公开号：US4399296A

  公开（公告）日：1983-08-16
• US4407811A
  申请人：——

  公开号：US4407811A

  公开（公告）日：1983-10-04
• US4448971A
  申请人：——

  公开号：US4448971A

  公开（公告）日：1984-05-15