(+)-(1'S,3'S)-methyl-1',3'-dihydroxy-γ-ionylideneacetate | 162585-04-8

• 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)-methyl-1',3'-dihydroxy-γ-ionylideneacetate
• 英文别名: methyl (2Z,4E)-5-[(1R,3S)-1,3-dihydroxy-2,2-dimethyl-6-methylidenecyclohexyl]-3-methylpenta-2,4-dienoate
• CAS: 162585-04-8
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: GDJVPFNQWRXIFX-RGFNJTRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(1'S,3'S)-methyl-1',3'-dihydroxy-γ-ionylideneacetate 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以71%的产率得到(+)-(R)-methyl-1'-hydroxy-3'-oxo-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：

  (+)-(1'S,3'S)-(2Z,4E)-5-(1',3'-dihydroxy-2',2'-dimethyl-6'-methylenecyclohexyl)-3-methyl-2,4-pentadiene-1-ol 在 manganese(IV) oxide 、 氰化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 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

文献信息

• Isolation and metabolism of 3′-hydroxy-γ-ionylideneacetic acids in Cercospora cruenta
  作者：Hiroshi Yamamoto、Takayuki Oritani、Takeshi Morita、Akira Tanaka

  DOI：10.1016/0031-9422(94)00702-u

  日期：1995.1

  Four isomers of 3'-hydroxy-gamma-ionylideneacetic acid were isolated from Cercospora cruenta cultures. The ratio of isomers was found to be 44:24:21:11 for (2Z,4E)-(1'S,3'S)-, (2Z,4E)-(1'S,3'R)-, (2E,4E)-(1'S,3'S)- and (2E,4E)-(1'S,3'R)-3'-hydroxy-gamma-acid, respectively. Feeding experiments with [C-14] labelled (2Z, 4E)-(1'S, 3'S)-3'-hydroxy-gamma-acid showed high incorporation into 1',3'-dihydroxy-gamma-acid and 1'-hydroxy-3'-oxo-gamma-acid, but not into 4'-hydroxy-gamma-acids. This result suggested that 3'-hydroxy-gamma-acids were not involved in the ABA biosynthetic pathway. The biological activities of these new metabolites were compared with those of known ABA biosynthetic intermediates.
• Chiral synthesis and stomatal closure activities of γ-pseudo- and dihydro-abscisic acids
  作者：Hiroshi Yamamoto、Takayuki Oritani

  DOI：10.1016/0031-9422(95)00374-g

  日期：1995.11

  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.