(1R,3R,5S)-3-(4-methoxybenzyl)-oxy-8-oxa-bicyclo<3.2.1>octan-6-one | 222172-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,3R,5S)-3-(4-methoxybenzyl)-oxy-8-oxa-bicyclo<3.2.1>octan-6-one
• CAS: 222172-08-9
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: CZWBDYYUWOXIPF-NFAWXSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3R,5S)-3-(4-methoxybenzyl)-oxy-8-oxa-bicyclo<3.2.1>octan-6-one 在 硫酸 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 <(2R,4R,6S)-6-methoxy-4-(4-methoxybenzyl)-oxy-tetrahydropyran-2-yl>-acetic acid methyl ester
  参考文献：
  名称：

  trans-C-Glycosides from 8-oxabicyclo[3.2.1]oct-6-en-3-one — Synthesis of the C3–C13 segment of the phorboxazoles A and B

  摘要：

  The enantiopure and fully resolved C3-C13 segment of the phorboxazoles A and B has been prepared in 14 steps in 24% overall yield starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one. Key steps are the desymmetrization of the oxabicyclic ketone, the anomeric allylation and the asymmetric allylboration. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01196-x
• 作为产物：
  描述：

  exo-8-oxabicyclo[3.2.1]oct-6-en-3-ol 在 四丁基碘化铵 、 sodium hydride 、 (+)-二异松蒎烯基硼烷 、 pyridinium chlorochromate 作用下， 反应 13.0h， 生成 (1R,3R,5S)-3-(4-methoxybenzyl)-oxy-8-oxa-bicyclo<3.2.1>octan-6-one
  参考文献：
  名称：

  trans-C-Glycosides from 8-oxabicyclo[3.2.1]oct-6-en-3-one — Synthesis of the C3–C13 segment of the phorboxazoles A and B

  摘要：

  The enantiopure and fully resolved C3-C13 segment of the phorboxazoles A and B has been prepared in 14 steps in 24% overall yield starting from 8-oxabicyclo[3.2.1]oct-6-en-3-one. Key steps are the desymmetrization of the oxabicyclic ketone, the anomeric allylation and the asymmetric allylboration. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01196-x