(1'S,3'S)-(Z)-5-(1'-hydroxy-2',2'-dimethyl-6'-methylene-3'-tetrahydropyranyloxycyclohexyl)-3-methyl-2-penten-4-yn-1-yl-tetrahydropyranyl ether | 170311-02-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1'S,3'S)-(Z)-5-(1'-hydroxy-2',2'-dimethyl-6'-methylene-3'-tetrahydropyranyloxycyclohexyl)-3-methyl-2-penten-4-yn-1-yl-tetrahydropyranyl ether
• CAS: 170311-02-1
• 化学式: C₂₅H₃₈O₅
• 分子量: 418.574
• InChiKey: XLGIKMQXCOUDCV-QMPCCMIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1'S,3'S)-(Z)-5-(1'-hydroxy-2',2'-dimethyl-6'-methylene-3'-tetrahydropyranyloxycyclohexyl)-3-methyl-2-penten-4-yn-1-yl-tetrahydropyranyl ether 在 manganese(IV) oxide 、 氰化钠 、 溶剂黄146 、 红铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 52.0h， 生成 (+)-(1'S,3'S)-methyl-1',3'-dihydroxy-γ-ionylideneacetate
  参考文献：
  名称：

  Chiral synthesis and stomatal closure activities of γ-pseudo- and dihydro-abscisic acids

  摘要：

  Analogues of abscisic acid (ABA) were prepared from chiral cyclohexanone building blocks. Synthetic (1'R, 3'S)-1',3'-gamma-dihydroxy-gamma-ionylideneacetic acid and (R)-1'-hydroxy-3'-oxo-gamma-ionylideneacetic acid (tentatively named gamma-pseudo-ABA) provided authentic data for new metabolities isolated from Cercospora cruenta. Both enantiomers of 2', 3'-dihydroABA were also prepared. Only the (1'S, 2'S)-isomer of 2', 3'-dihydroABA induced substantial closure of stomata on the epidermal strips of Commelina communis.

  DOI：

  10.1016/0031-9422(95)00374-g
• 作为产物：
  描述：

  (Z)-3-Methyl-2-penten-4-ynyl tetrahydropyranyl ether 、 (-)-(S)-2,2-dimethyl-6-methylene-3-tetrahydropyranoxy-1-cyclohexanone 在 溴化乙啶 、 magnesium 作用下， 生成 (1R,5S)-2,6,6-Trimethyl-1-[(Z)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-pent-3-en-1-ynyl]-5-(tetrahydro-pyran-2-yloxy)-cyclohex-2-enol 、 (1'R,3'S)-(Z)-5-(1'-hydroxy-2',2'-dimethyl-6'-methylene-3'-tetrahydropyranyloxycyclohexyl)-3-methyl-2-penten-4-yn-1-yl-tetrahydropyranyl ether 、 (1'S,3'S)-(Z)-5-(1'-hydroxy-2',2'-dimethyl-6'-methylene-3'-tetrahydropyranyloxycyclohexyl)-3-methyl-2-penten-4-yn-1-yl-tetrahydropyranyl ether
  参考文献：
  名称：

  Chiral synthesis and stomatal closure activities of γ-pseudo- and dihydro-abscisic acids

  摘要：

  Analogues of abscisic acid (ABA) were prepared from chiral cyclohexanone building blocks. Synthetic (1'R, 3'S)-1',3'-gamma-dihydroxy-gamma-ionylideneacetic acid and (R)-1'-hydroxy-3'-oxo-gamma-ionylideneacetic acid (tentatively named gamma-pseudo-ABA) provided authentic data for new metabolities isolated from Cercospora cruenta. Both enantiomers of 2', 3'-dihydroABA were also prepared. Only the (1'S, 2'S)-isomer of 2', 3'-dihydroABA induced substantial closure of stomata on the epidermal strips of Commelina communis.

  DOI：

  10.1016/0031-9422(95)00374-g