4-oxo-2,3-didehydro-7,8-dihydro-β-ionone | 20026-81-7

• 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: 4-oxo-2,3-didehydro-7,8-dihydro-β-ionone
• 英文别名: 3-(3'-oxobutyl)-2,4,4-trimethylcyclohexa-2,5-dienone；2,4,4-Trimethyl-3-(3-oxobutyl)cyclohexa-2,5-dien-1-one
• CAS: 20026-81-7
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: FQBSMSHWOZHTFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(3'-hydroxybutyl)-2,4,4-trimethylcyclohexa-2,5-dienone 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.25h， 以20 g的产率得到4-oxo-2,3-didehydro-7,8-dihydro-β-ionone
  参考文献：
  名称：

  Synthesis of Natural Oxygenated Monocarbocyclic Sesquiterpenoids from 6,7-Epoxygeranyl Acetate

  摘要：

  Natural sesquiterpenes 5-(2/,5'-epoxy-2',6',6'-trimethyl)cyclohexyl-3-methyl-1-penten-3-ol (5), cis-3-[(E)-5'-hydroxy-3'-methyl-3'-pentenyl]-2,2-dimethyl-4-methylenecyclohexanol (elegansidiol) (6), 4-(5'-acetoxy-2',6',6'-trimethyl)cyclohex-2'-enyl-3-methyl-1-penten-3-ol (7) and 5-acetoxy-3-(3-hydroxy-3-methylpent-4-enyl)2,4,4-trimethylcyclohex-2-enone (8) were prepared from 6,7-epoxygeranyl acetate (9), via (2',5'-epoxy-2',6',6'-trimethyl)cyclohexylmethyl tosylate (10), for the first time. 5 is an intermediate in the synthesis of the sesquiterpene-coumarin ether (+/-)-farnesiferol C (1). The preparation of suitable intermediates for synthesising related natural farmesiferol B (3) and D (4) is also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00560-3

文献信息

• Fermentation of Fragrances: Biotransformation of ?-Ionone by Lasiodiplodia theobromae
  作者：Victor Krasnobajew、Daniel Helmlinger

  DOI：10.1002/hlca.19820650532

  日期：1982.7.28

  Pre-grown mycelia of Lasiodiplodia theobromae ATCC 28570 transform β-ionone (1) into a large variety of metabolites, by mainly degrading the side-chain of the β-ionone molecule by a C2-unity. The enzyme system responsible for this degradation is proposed to be an oxygenase, which gives rise to the formation of the main product β-cyclo-homogeraniol (8) in analogy to a Baeyer- Villiger oxidation. Further

  拉氏单胞菌ATCC 28570的预先生长的菌丝体主要通过C 2统一降解β-紫罗兰酮分子的侧链，从而将β-紫罗兰酮（1）转变为多种代谢产物。有人提出负责这种降解的酶系统是一种加氧酶，它类似于Baeyer- Villiger氧化反应，导致形成了主要产物β-环-香薄荷醇（8）。Lasiodiplodia的进一步酶促作用，例如氢化和羟基化，导致一些尚未描述的β-紫罗兰酮代谢物的积累。

表征谱图