(1RS,5RS,6SR,7RS)-1-(hydroxymethyl)-7-(4-hydroxyphenyl)-4-oxo-8-oxabicyclo[3.2.1]oct-3-ene-6-carboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1RS,5RS,6SR,7RS)-1-(hydroxymethyl)-7-(4-hydroxyphenyl)-4-oxo-8-oxabicyclo[3.2.1]oct-3-ene-6-carboxylic acid
• 英文别名: (1S,5S,6R,7S)-1-(hydroxymethyl)-7-(4-hydroxyphenyl)-4-oxo-8-oxabicyclo[3.2.1]oct-2-ene-6-carboxylic acid
• 化学式: C₁₅H₁₄O₆
• 分子量: 290.273
• InChiKey: IJGLRFRYPAUECC-RGCMKSIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104.06
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-羟基肉桂酸甲酯 在 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基吡啶 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 34.58h， 生成 (1RS,5RS,6SR,7RS)-1-(hydroxymethyl)-7-(4-hydroxyphenyl)-4-oxo-8-oxabicyclo[3.2.1]oct-3-ene-6-carboxylic acid
  参考文献：
  名称：

  Synthesis of the 5-hydroxymethyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural products descurainin and cartorimine

  摘要：

  Reaction of pyranulose 6 with styrenes 12c or 13 and Et3N in CH2O2 at 25 degrees C afforded the [5+2] cycloadducts 14c and 15, which were hydrolyzed to give the natural products I and descurainin (2) in 24 and 27% overall yield, respectively. Heating pyranulose 6 with cinnamate ester 21 in the presence of 2,6-di-t-butylpyridine in CH3CN at 175 degrees C afforded the [5+2] cycloadduct, which was hydrolyzed to give cartorimine (3) in 13% yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.083

文献信息

• Synthesis of (±)-cartorimine
  作者：Barry B. Snider、James F. Grabowski

  DOI：10.1016/j.tetlet.2004.12.007

  日期：2005.1

  Heating pyranulose 4 and cinnamate 2 in the presence of 2,6-di-t-butylpyridine in CH3CN afforded the [5 divided by 2] cycloadduct, which was hydrolyzed to give 13% of cartorimine (1). (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of the 5-hydroxymethyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural products descurainin and cartorimine
  作者：Barry B. Snider、James F. Grabowski

  DOI：10.1016/j.tet.2005.10.083

  日期：2006.5

  Reaction of pyranulose 6 with styrenes 12c or 13 and Et3N in CH2O2 at 25 degrees C afforded the [5+2] cycloadducts 14c and 15, which were hydrolyzed to give the natural products I and descurainin (2) in 24 and 27% overall yield, respectively. Heating pyranulose 6 with cinnamate ester 21 in the presence of 2,6-di-t-butylpyridine in CH3CN at 175 degrees C afforded the [5+2] cycloadduct, which was hydrolyzed to give cartorimine (3) in 13% yield. (c) 2006 Elsevier Ltd. All rights reserved.