3,4-didehydro-β-ionol | 116296-79-8

• 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: 3,4-didehydro-β-ionol
• 英文别名: 3,4-Didehydro-beta-ionol；(E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-ol
• CAS: 116296-79-8
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: SJICFWRZYCWFOK-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,4-didehydro-β-ionol 在 柠檬酸 作用下， 以 水 为溶剂， 反应 1.0h， 以80%的产率得到2,2,6,7-tetramethylbicyclo<4.3.0>nona-4,7,9(1)-triene
  参考文献：
  名称：

  Identification of new constituents of quince fruit flavor (Cydonia oblonga Mill. = C. vulgaris Pers.)

  摘要：

  DOI：

  10.1021/jo00354a016
• 作为产物：
  描述：

  (3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以4.2 g的产率得到3,4-didehydro-β-ionol
  参考文献：
  名称：

  2-(2-Butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran: A New Degradation Product of 3-Hydroxy-5,6-epoxy-.beta.-ionol

  摘要：

  Identification of 2-(2-butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran diastereomers (4, 5) in various leaves [stinging nettle; sloe tree; strawberry; vine (Riesling); sweet silique (Bunias orientalis)] was achieved by comparison of HRGC retention and spectral (MS; vapor phase FTIR) data with those of synthetic references. Model experiments revealed their acid-catalyzed formation from 3-hydroxy-5,6-epoxy-beta-ionol that was present in glycosidically bound form in the above-mentioned leaves. Assignment of the isomers 4a/4b and 5a/5b was established by NOE experiments. Enantiodifferentiation carried out by on-line coupled multidimensional gas chromatography-mass spectrometry revealed the occurrence of enantiomerically pure 5S enantiomers 4b/5b in the natural sources. A pathway for the selective formation of 4b/5b in nature is proposed.

  DOI：

  10.1021/jf00048a044

文献信息

• A C13-norisoprenoid gentiobioside from quince fruit
  作者：Peter Winterhalter、Sven Harmsen、Franco Trani

  DOI：10.1016/s0031-9422(00)98244-x

  日期：1991.1

  a-D-glucopyranoside] of 3-hydroxy-beta-ionol has been isolated and characterized in quince (Cydonia oblonga) fruit through spectral and chemical studies. Model experiments carried out with this new natural compound revealed its important role as precursor of a number of C13-norisoprenoid flavour compounds of quince essential oil.

  3-羟基-β-紫罗兰醇的β-D-龙胆二糖苷[β-D-吡喃葡萄糖基(1----6)-β-D-吡喃葡萄糖苷]已在榅桲（Cydonia oblonga）果实中通过光谱和化学研究。用这种新的天然化合物进行的模型实验揭示了它作为木瓜精油的许多 C13-降甲异戊二烯风味化合物的前体的重要作用。
• 237. Studies in the polyene series. Part XXXVII. Preparation of 3-dehydro-β-ionone and some 3-substituted β-ionones
  作者：H. B. Henbest

  DOI：10.1039/jr9510001074

  日期：——
• Identification of new constituents of quince fruit flavor (Cydonia oblonga Mill. = C. vulgaris Pers.)
  作者：Masakazu Ishihara、Tomoyuki Tsuneya、Haruyasu Shiota、Minoru Shiga、Kazumi Nakatsu

  DOI：10.1021/jo00354a016

  日期：1986.2
• 2-(2-Butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran: A New Degradation Product of 3-Hydroxy-5,6-epoxy-.beta.-ionol
  作者：Wolfgang Neugebauer、Peter Winterhalter、Peter Schreier

  DOI：10.1021/jf00048a044

  日期：1994.12

  Identification of 2-(2-butenylidene)-3,3-dimethyl-5-(2-oxopropyl)tetrahydrofuran diastereomers (4, 5) in various leaves [stinging nettle; sloe tree; strawberry; vine (Riesling); sweet silique (Bunias orientalis)] was achieved by comparison of HRGC retention and spectral (MS; vapor phase FTIR) data with those of synthetic references. Model experiments revealed their acid-catalyzed formation from 3-hydroxy-5,6-epoxy-beta-ionol that was present in glycosidically bound form in the above-mentioned leaves. Assignment of the isomers 4a/4b and 5a/5b was established by NOE experiments. Enantiodifferentiation carried out by on-line coupled multidimensional gas chromatography-mass spectrometry revealed the occurrence of enantiomerically pure 5S enantiomers 4b/5b in the natural sources. A pathway for the selective formation of 4b/5b in nature is proposed.