(2R,4S)-4-(4-benzyloxybenzyl)-2-phenyl-5-oxodioxolane | 1141933-40-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4S)-4-(4-benzyloxybenzyl)-2-phenyl-5-oxodioxolane
• 英文别名: (2R,5S)-2-phenyl-5-[(4-phenylmethoxyphenyl)methyl]-1,3-dioxolan-4-one
• CAS: 1141933-40-5
• 化学式: C₂₃H₂₀O₄
• 分子量: 360.409
• InChiKey: UDKZOMRHTWGSHV-JTHBVZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4S)-4-(4-benzyloxybenzyl)-2-phenyl-5-oxodioxolane 、 2-溴乙酸苄酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 以65%的产率得到benzyl [(2R,4S)-4-(4-benzyloxybenzyl)-2-phenyl-5-oxodioxolan-4-yl]acetate
  参考文献：
  名称：

  (R)-Eucomic acid, a leaf-opening factor of the model organism, Lotus japonicus

  摘要：

  In the post-genomic era, the biological activity of endogenous metabolites can be linked to genomic information via its target protein. Consequently, studies concerned with the identification of endogenous bioactive metabolites from model organisms should be undertaken. (R)-Eucomic acid (1) was identified as an endogenous metabolite concerning leaf movement in the model legume, Lotus japonicus. Absolute stereochemistry was investigated by comparison of physical characteristics of natural and synthetic enantiomers of 1. Identification of endogenous metabolites in a model legume would be particularly advantageous for further studies on the chemical biology of this biologically intriguing phenomenon. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.097
• 作为产物：
  描述：

  苯甲醛 、 (S)-3-(4-苄氧基苯基)-2-羟基丙酸 在 硫酸 、 对甲苯磺酸 作用下， 以 乙酸乙酯 、 正戊烷 为溶剂， 反应 24.0h， 以23%的产率得到(2S,4S)-4-(4-benzyloxybenzyl)-2-phenyl-5-oxodioxolane
  参考文献：
  名称：

  (R)-Eucomic acid, a leaf-opening factor of the model organism, Lotus japonicus

  摘要：

  In the post-genomic era, the biological activity of endogenous metabolites can be linked to genomic information via its target protein. Consequently, studies concerned with the identification of endogenous bioactive metabolites from model organisms should be undertaken. (R)-Eucomic acid (1) was identified as an endogenous metabolite concerning leaf movement in the model legume, Lotus japonicus. Absolute stereochemistry was investigated by comparison of physical characteristics of natural and synthetic enantiomers of 1. Identification of endogenous metabolites in a model legume would be particularly advantageous for further studies on the chemical biology of this biologically intriguing phenomenon. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.11.097

文献信息

• (R)-Eucomic acid, a leaf-opening factor of the model organism, Lotus japonicus
  作者：Masahiro Okada、Sungwook Park、Takahiro Koshizawa、Minoru Ueda

  DOI：10.1016/j.tet.2008.11.097

  日期：2009.3

  In the post-genomic era, the biological activity of endogenous metabolites can be linked to genomic information via its target protein. Consequently, studies concerned with the identification of endogenous bioactive metabolites from model organisms should be undertaken. (R)-Eucomic acid (1) was identified as an endogenous metabolite concerning leaf movement in the model legume, Lotus japonicus. Absolute stereochemistry was investigated by comparison of physical characteristics of natural and synthetic enantiomers of 1. Identification of endogenous metabolites in a model legume would be particularly advantageous for further studies on the chemical biology of this biologically intriguing phenomenon. (C) 2008 Elsevier Ltd. All rights reserved.