endo-6-(4-hydroxy-3-methoxyphenyl)-5-(hydroxymethyl)-8-oxabicyclo[3.2.1]oct-3-en-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: endo-6-(4-hydroxy-3-methoxyphenyl)-5-(hydroxymethyl)-8-oxabicyclo[3.2.1]oct-3-en-2-one
• 英文别名: (1S,5S,6R)-6-(4-hydroxy-3-methoxyphenyl)-5-(hydroxymethyl)-8-oxabicyclo[3.2.1]oct-3-en-2-one
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: SBABHRISUMETAV-WKPIXPDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  Acetic acid (1S,5S,7R)-7-(4-hydroxy-3-methoxy-phenyl)-4-oxo-8-oxa-bicyclo[3.2.1]oct-2-en-1-ylmethyl ester 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以69 mg的产率得到endo-6-(4-hydroxy-3-methoxyphenyl)-5-(hydroxymethyl)-8-oxabicyclo[3.2.1]oct-3-en-2-one
  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

• Catalytic Asymmetric Synthesis of the <i>endo</i>-6-Aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one Natural Product from <i>Ligusticum chuanxing</i> via 1,3-Dipolar Cycloaddition of a Formyl-Derived Carbonyl Ylide Using Rh₂(<i>S</i>-TCPTTL)₄
  作者：Naoyuki Shimada、Taiki Hanari、Yasunobu Kurosaki、Koji Takeda、Masahiro Anada、Hisanori Nambu、Motoo Shiro、Shunichi Hashimoto

  DOI：10.1021/jo101175b

  日期：2010.9.3

  The reaction of a six-membered cyclic formyl-carbonyl ylide derived from α-diazo-β-ketoester with phenylacetylene derivatives under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh2(S-TCPTTL)4, provides cycloadducts containing an 8-oxabicyclo[3.2.1]octane ring system in up to 97% ee. This represents the first example of an enantioselective 1,3-dipolar cycloaddition

  六元环状甲酰基羰基叶立德的反应从α重氮基β酮酯与苯乙炔衍生物的二铑的催化下（II）四[ Ñ -tetrachlorophthaloyl-（小号） -叔-leucinate]的Rh 2（S- TCPTTL）4，提供包含高达97％ee的8-氧杂双环[3.2.1]辛烷环系统的环加合物。这代表了环状甲酰基-羰基内酯的对映选择性1，3-偶极环加成的第一个例子。使用该催化过程中，不对称合成内切-6-芳基-8-氧杂双环[3.2.1]辛-3-烯-2-酮的天然产物1从藁传兴园艺。已经实现。