2,4,4-trimethyl-3-((1E,3E)-3-methyl-7-oxo-octa-1,3-dienyl)cyclohex-2-enone | 77399-83-8

• 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: 2,4,4-trimethyl-3-((1E,3E)-3-methyl-7-oxo-octa-1,3-dienyl)cyclohex-2-enone
• 英文别名: trisporin B；2,4,4-trimethyl-3-[(1E,3E)-3-methyl-7-oxoocta-1,3-dienyl]cyclohex-2-en-1-one
• CAS: 77399-83-8
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: NRECYSCADKAJKM-GSSAJISUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,4-trimethyl-3-((1E,3E)-3-methyl-7-oxo-octa-1,3-dienyl)cyclohex-2-enone 在 (+)-mating type Blakeslea trispora cells 作用下， 反应 48.0h， 生成 methyl 2-((1E,3E)-7-hydroxy-3-methylocta-1,3-dienyl)-1,3-dimethyl-4-oxocyclohex-2-enecarboxylate
  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：

  6-甲基-5-庚烯-2-酮 、 (E)-2,4,4-trimethyl-3-(3'-methyl-1',3'-butadienyl)-2-cyclohexen-1-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 生成 trisporin B 、 2,4,4-trimethyl-3-((1E,3E)-3-methyl-7-oxo-octa-1,3-dienyl)cyclohex-2-enone
  参考文献：
  名称：

  三孢菌素的一种方便的跨复分解方法

  摘要：

  使用交叉复分解是关键步骤的策略已制备了三个系列的三孢菌素。已证明该反应是高度区域选择性的，使得具有1，1-取代的烯烃的α-或β-紫罗兰酮衍生物与三取代的烯烃结合。通过光谱方法已经确定了新形成的烯烃的立体化学。

  DOI：

  10.1016/j.tet.2009.09.074

文献信息

• Efficient Generation of a Trisporoid Library by Combination of Synthesis and Biotransformation
  作者：Doreen Schachtschabel、Wilhelm Boland

  DOI：10.1021/jo062236c

  日期：2007.2.1

  [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.
• A convenient cross-metathesis approach to trisporins
  作者：Cristóbal López-Sánchez、Carmen Hernández-Cervantes、Antonio Rosales、Míriam Álvarez-Corral、Manuel Muñoz-Dorado、Ignacio Rodríguez-García

  DOI：10.1016/j.tet.2009.09.074

  日期：2009.11

  cross-metathesis is the key step. This reaction has proved to be highly regioselective, allowing the combination of α- or β-ionone derivatives having a 1,1-disustituted olefin with trisubstituted alkenes. The stereochemistry of the newly formed olefins has been established by spectroscopic means.

  使用交叉复分解是关键步骤的策略已制备了三个系列的三孢菌素。已证明该反应是高度区域选择性的，使得具有1，1-取代的烯烃的α-或β-紫罗兰酮衍生物与三取代的烯烃结合。通过光谱方法已经确定了新形成的烯烃的立体化学。