3-(3-(3,4,5-Trimethoxyphenyl)prop-1-(E)-enyl)-4-(R)-ethyloxazolidin-2-one | 1296671-51-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3-(3,4,5-Trimethoxyphenyl)prop-1-(E)-enyl)-4-(R)-ethyloxazolidin-2-one
• CAS: 1296671-51-6
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: JCFFDOIITUHLSN-STMXVASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(3-(3,4,5-Trimethoxyphenyl)prop-1-(E)-enyl)-4-(R)-ethyloxazolidin-2-one 、 (E)-methyl 4-(benzo[d][1,3]dioxol-5-yl)-2-oxobut-3-enoate 在 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 作用下， 以 环己烷 为溶剂， 反应 168.0h， 以34%的产率得到(2R,3R,4S)-4-(benzo[d][1,3]dioxol-5-yl)-3-(3,4,5-trimethoxybenzyl)-2-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-3,4-dihydro-2H-pyran-6-carboxylic acid methyl ester
  参考文献：
  名称：

  New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin

  摘要：

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.097
• 作为产物：
  描述：

  3,4,5-三甲氧基肉桂酸 在 lithium aluminium tetrahydride 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 3-(3-(3,4,5-Trimethoxyphenyl)prop-1-(E)-enyl)-4-(R)-ethyloxazolidin-2-one
  参考文献：
  名称：

  New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin

  摘要：

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.097