3-((1E)-4-bromo-3-methylbuta-1,3-dienyl)-2,4,4-trimethylcyclohex-2-enone | 929626-31-3

• 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-((1E)-4-bromo-3-methylbuta-1,3-dienyl)-2,4,4-trimethylcyclohex-2-enone
• CAS: 929626-31-3
• 化学式: C₁₄H₁₉BrO
• 分子量: 283.208
• InChiKey: DJJMTRUZZAYCAZ-CGIVJHKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-((1E)-4-bromo-3-methylbuta-1,3-dienyl)-2,4,4-trimethylcyclohex-2-enone 在 4-二甲氨基吡啶 、 氢氟酸 、 碘 、 锌 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 生成 3-((1E)-7-hydroxy-3-methylocta-1,3-dienyl)-2,4,4-trimethylcyclohex-2-enone
  参考文献：
  名称：

  Efficient Generation of a Trisporoid Library by Combination of Synthesis and Biotransformation

  摘要：

  [GRAPHIC]Trisporic acids and their biosynthetic precursors represent a family of powerful fungal pheromones and morphogenetic factors. A highly flexible synthetic protocol is described that (i) provides rapid access to nonfunctionalized early trisporoids from beta-ionone, (ii) includes a regiospecific oxidative functionalization of beta-ionone leading to 1-acetoxy-beta-ionone giving access to functionalized trisporoids, and (iii) utilizes a biotransformation of early synthetic trisporoids by growing cells of Blakeslea trispora to prepare late trisporoids including trisporic acids. The same protocol also provides deuterium-labeled trisporoids such as trisporin B [H-2(3)]-19. Administration of [H-2(3)]-19 to growing cells of the (-)-mating type of B. trispora resulted in the formation of the labeled trisporols [H-2(3)]-20 and [H-2(3)]-21. Growing cultures containing both mating types can be used to prepare trisporic acids from early precursors.

  DOI：

  10.1021/jo062236c
• 作为产物：
  描述：

  2,4,4-trimethyl-3-(3-oxobut-1-enyl)cyclohex-2-enyl acetate 在 manganese(IV) oxide 、 氢氧化钾 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 3-((1E)-4-bromo-3-methylbuta-1,3-dienyl)-2,4,4-trimethylcyclohex-2-enone
  参考文献：
  名称：

  Efficient Generation of a Trisporoid Library by Combination of Synthesis and Biotransformation

  摘要：

  [GRAPHIC]Trisporic acids and their biosynthetic precursors represent a family of powerful fungal pheromones and morphogenetic factors. A highly flexible synthetic protocol is described that (i) provides rapid access to nonfunctionalized early trisporoids from beta-ionone, (ii) includes a regiospecific oxidative functionalization of beta-ionone leading to 1-acetoxy-beta-ionone giving access to functionalized trisporoids, and (iii) utilizes a biotransformation of early synthetic trisporoids by growing cells of Blakeslea trispora to prepare late trisporoids including trisporic acids. The same protocol also provides deuterium-labeled trisporoids such as trisporin B [H-2(3)]-19. Administration of [H-2(3)]-19 to growing cells of the (-)-mating type of B. trispora resulted in the formation of the labeled trisporols [H-2(3)]-20 and [H-2(3)]-21. Growing cultures containing both mating types can be used to prepare trisporic acids from early precursors.

  DOI：

  10.1021/jo062236c

文献信息

• Biological activity of trisporoids and trisporoid analogues in Mucor mucedo (−)
  作者：Doreen Schachtschabel、Christine Schimek、Johannes Wöstemeyer、Wilhelm Boland

  DOI：10.1016/j.phytochem.2005.04.022

  日期：2005.6

  In the course of their sexual interactions, zygomycete fungi communicate via an elaborate series of carotene-derived compounds, namely trisporic acid and its biosynthetic progenitors. A novel building-block strategy allowed the systematic generation of structurally modified trisporoids along with putative early biosynthetic precursors for physiological tests. The impact of discrete structural elements was documented by the ability of individual compounds to induce sexually committed hyphae in Mucor mucedo. The activity screening contributed to establish general structure-function relationships for trisporoid action. Most crucial for activity were the dimension of the longer side chain, the polarity of functional groups at C(4) and C(13), and the number of conjugated double bonds in the side chain. The presence of an oxygen substituent at the cyclohexene ring is not essential for function. The overall biological activity apparently results from the combination of the various structural elements. (c) 2005 Elsevier Ltd. All rights reserved.