(R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one | 1329428-58-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one
• 英文别名: (4R)-3-[(E)-3-(2,5-dimethoxy-4-methylphenyl)prop-2-enoyl]-4-phenyl-1,3-oxazolidin-2-one
• CAS: 1329428-58-1
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: SPIQQGYSWBFIJN-FVNWOWOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one 在 sodium tetrahydroborate 、 copper(I) bromide dimethylsulfide complex 、 二甲基硫 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.17h， 生成 (R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid
  参考文献：
  名称：

  Enantioselective syntheses of the assigned structures of the helibisabonols A and B

  摘要：

  The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the sigma-symmetrical diol (route a) and a diastereoselective conjugate addition of the methyl to the enone with a chiral auxiliary (route b) we constructed the key tertiary stereogenic center at the benzylic position (C7) and then used an asymmetric dihydroxylation for assembling the C10 stereogenic center. In addition, possible diastereoisomers of the natural products were prepared and detailed comparisons of the H-1 and C-13 NMR spectra were conducted. As a result, the structure originally assigned to helibisabonol A may be revised to (7R,10R)-1. In the case of helibisabonol B, the (7R,10R)-2 would be reasonable based on a comparison of the NMR data and the biogenetic parallelism with helibisabonol A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.064
• 作为产物：
  描述：

  1-溴-2,5-二甲氧基-4-甲基苯 、 (R)-3-acryloyl-4-phenyloxazolidin-2-one 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以81%的产率得到(R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Enantioselective syntheses of the assigned structures of the helibisabonols A and B

  摘要：

  The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the sigma-symmetrical diol (route a) and a diastereoselective conjugate addition of the methyl to the enone with a chiral auxiliary (route b) we constructed the key tertiary stereogenic center at the benzylic position (C7) and then used an asymmetric dihydroxylation for assembling the C10 stereogenic center. In addition, possible diastereoisomers of the natural products were prepared and detailed comparisons of the H-1 and C-13 NMR spectra were conducted. As a result, the structure originally assigned to helibisabonol A may be revised to (7R,10R)-1. In the case of helibisabonol B, the (7R,10R)-2 would be reasonable based on a comparison of the NMR data and the biogenetic parallelism with helibisabonol A. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.064

文献信息

• Enantioselective syntheses of the assigned structures of the helibisabonols A and B
  作者：Akari Miyawaki、Mayu Osaka、Makoto Kanematsu、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tet.2011.03.064

  日期：2011.9

  The enantioselective syntheses of the compounds with the assigned structures of the helibisabonols A and B have been accomplished. Using an enzymatic desymmetrization of the sigma-symmetrical diol (route a) and a diastereoselective conjugate addition of the methyl to the enone with a chiral auxiliary (route b) we constructed the key tertiary stereogenic center at the benzylic position (C7) and then used an asymmetric dihydroxylation for assembling the C10 stereogenic center. In addition, possible diastereoisomers of the natural products were prepared and detailed comparisons of the H-1 and C-13 NMR spectra were conducted. As a result, the structure originally assigned to helibisabonol A may be revised to (7R,10R)-1. In the case of helibisabonol B, the (7R,10R)-2 would be reasonable based on a comparison of the NMR data and the biogenetic parallelism with helibisabonol A. (C) 2011 Elsevier Ltd. All rights reserved.