meso-(1R,4S,6s)-6-(benzyloxy)cyclohept-2-ene-1,4-diol | 217025-86-0

• 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: meso-(1R,4S,6s)-6-(benzyloxy)cyclohept-2-ene-1,4-diol
• CAS: 217025-86-0
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: WRXVWFTXDAHVTE-WDNDVIMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  meso-(1R,4S,6s)-6-(benzyloxy)cyclohept-2-ene-1,4-diol 在 四氧化锇 吡啶 、 4-二甲氨基吡啶 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 20.0h， 生成 meso-(1R,2S,3S,5s,7R)-5-(benzyloxy)-3,7-bis((2,2-dimethylpropionyl)oxy)cycloheptane-1,2-diol
  参考文献：
  名称：

  Reagent Control of Geometric Selectivity and Enantiotopic Group Preference in Asymmetric Horner−Wadsworth−Emmons Reactions with meso-Dialdehydes

  摘要：

  Results from asymmetric Horner-Wadsworth-Emmons reactions between chiral phosphsnate reagents 3a-d, which contain (1R,2S,5R)-8-phenylmenthol as a chiral auxiliary, and meso-dialdehydes 6 and 14 are presented. It was found that both the geometric selectivities and the levels of asymmetric induction depended on the structure of the phosphonate (i.e., the alkyl group R-1 in the phosphoryl unit) and to a certain extent also on the reaction conditions. Furthermore, the nature of the protecting group used on the a-oxygen substituent in dialdehydes 14 influenced the outcome somewhat. By an appropriate choice of reagent and conditions, either (E)- or (Z)-monoaddition products could be obtained geometrically pure and with good to excellent diastereoselectivities, in synthetically useful yields. Analyses of the absolute configurations of the products showed that the (E)-selective reagents (3a-c) and the (Z)-selective phosphonate 3d reacted at opposite enantiotopic carbonyl groups in the substrates. A mechanistic model which accounts for the products formed is presented.

  DOI：

  10.1021/jo981102z
• 作为产物：
  描述：

  6-(benzyloxy)-1,3-cycloheptadiene 在 palladium diacetate manganese(IV) oxide 、 氢氧化钾 、 对苯醌 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 0.5h， 生成 meso-(1R,4S,6s)-6-(benzyloxy)cyclohept-2-ene-1,4-diol
  参考文献：
  名称：

  Reagent Control of Geometric Selectivity and Enantiotopic Group Preference in Asymmetric Horner−Wadsworth−Emmons Reactions with meso-Dialdehydes

  摘要：

  Results from asymmetric Horner-Wadsworth-Emmons reactions between chiral phosphsnate reagents 3a-d, which contain (1R,2S,5R)-8-phenylmenthol as a chiral auxiliary, and meso-dialdehydes 6 and 14 are presented. It was found that both the geometric selectivities and the levels of asymmetric induction depended on the structure of the phosphonate (i.e., the alkyl group R-1 in the phosphoryl unit) and to a certain extent also on the reaction conditions. Furthermore, the nature of the protecting group used on the a-oxygen substituent in dialdehydes 14 influenced the outcome somewhat. By an appropriate choice of reagent and conditions, either (E)- or (Z)-monoaddition products could be obtained geometrically pure and with good to excellent diastereoselectivities, in synthetically useful yields. Analyses of the absolute configurations of the products showed that the (E)-selective reagents (3a-c) and the (Z)-selective phosphonate 3d reacted at opposite enantiotopic carbonyl groups in the substrates. A mechanistic model which accounts for the products formed is presented.

  DOI：

  10.1021/jo981102z