(+/-)-4-(1'-hydroxy-2'-difluoromethyl-2',6'-dimethylcyclohexyl)but-3-yn-2-ol | 164359-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-4-(1'-hydroxy-2'-difluoromethyl-2',6'-dimethylcyclohexyl)but-3-yn-2-ol
• CAS: 164359-88-0
• 化学式: C₁₃H₂₀F₂O₂
• 分子量: 246.297
• InChiKey: WWYCISIEUNXRDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+/-)-4-(1'-hydroxy-2'-difluoromethyl-2',6'-dimethylcyclohexyl)but-3-yn-2-ol 在 manganese(IV) oxide 、 红铝 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 反应 45.0h， 生成 (+/-)-(2E,4E)-methyl 5-(6'-difluoromethyl-2',6'-dimethyl-1'-cyclohexen-1'-yl)-3-methyl-2,4-pentadienoate
  参考文献：
  名称：

  8′,8′-Difluoro- and 8′,8′,8′-trifluoroabscisic acids as highly potent, long-lasting analogues of abscisic acid

  摘要：

  Racemic 8',8'-difluoroabscisic acid (difluoro-ABA) and 8',8',8'-trifluoroabscisic acid (trifluoro-ABA) were synthesized as highly potent, long-lasting analogues of abscisic acid (ABA). The individual optical isomers were obtained by optical resolution of the racemic mixture by HPLC with a chiral column. (+)-8',8'-Difluoro-ABA and (+)-8',8',8'-trifluoro-ABA inhibited the elongation of rice seedlings six and 30 times more strongly, respectively, than (+)-ABA. These analogues also showed double the (+)-ABA-induced inhibition of lettuce seed germination. In causing stomatal closure and inhibiting the induction of alpha-amylase by gibberellin A(3), these analogues were equally as effective as ( +)-ABA. The high activity in the assays over a long period suggested that the metabolism of difluoro- and trifluoro-ABAs was delayed. (-)-Enantiomers were equal to, or weaker than(-)-ABA in the assays.

  DOI：

  10.1016/0031-9422(94)00693-n
• 作为产物：
  描述：

  (+/-)-2-formyl-2,6-dimethyl-1-cyclohexanone 在 正丁基锂 、 二乙胺基三氟化硫 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 (+/-)-4-(1'-hydroxy-2'-difluoromethyl-2',6'-dimethylcyclohexyl)but-3-yn-2-ol
  参考文献：
  名称：

  8′,8′-Difluoro- and 8′,8′,8′-trifluoroabscisic acids as highly potent, long-lasting analogues of abscisic acid

  摘要：

  Racemic 8',8'-difluoroabscisic acid (difluoro-ABA) and 8',8',8'-trifluoroabscisic acid (trifluoro-ABA) were synthesized as highly potent, long-lasting analogues of abscisic acid (ABA). The individual optical isomers were obtained by optical resolution of the racemic mixture by HPLC with a chiral column. (+)-8',8'-Difluoro-ABA and (+)-8',8',8'-trifluoro-ABA inhibited the elongation of rice seedlings six and 30 times more strongly, respectively, than (+)-ABA. These analogues also showed double the (+)-ABA-induced inhibition of lettuce seed germination. In causing stomatal closure and inhibiting the induction of alpha-amylase by gibberellin A(3), these analogues were equally as effective as ( +)-ABA. The high activity in the assays over a long period suggested that the metabolism of difluoro- and trifluoro-ABAs was delayed. (-)-Enantiomers were equal to, or weaker than(-)-ABA in the assays.

  DOI：

  10.1016/0031-9422(94)00693-n