5,9,13-trimethyl-4,8,12-tetradecatrienal | 66408-55-7

• 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: 5,9,13-trimethyl-4,8,12-tetradecatrienal
• 英文别名: 5,9,13-trimethyltetradeca-4,8,12-trienal；farnesyl-acetaldehyde；farnesylacetaldehyde
• CAS: 66408-55-7
• 化学式: C₁₇H₂₈O
• 分子量: 248.409
• InChiKey: IDHMAJKSCCNULC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,9,13-trimethyl-4,8,12-tetradecatrienal 在 4-二甲氨基吡啶 、 Oxone 、 Schwartz's reagent 、 四丙基高钌酸铵 、 Shi's ketone 、 palladium 10% on activated carbon 、 三氟化硼乙醚 、 氢气 、 氧气 、 四丁基硫酸氢铵 、 碳酸氢钠 、 potassium carbonate 、 臭氧 、 N-甲基吗啉氧化物 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 27.58h， 生成 (2S,4aR,5aS,10aR,12aS)-2-((R)-4-((2S,3S,6R)-6-bromo-3-hydroxy-3,7,7-trimethyloxepan-2-yl)-2-hydroxybutan-2-yl)-5a,9,9,12a-tetramethyldecahydro-2H-oxepino[3,2-b]pyrano[2,3-f]oxepin-8(9H)-one
  参考文献：
  名称：

  Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades

  摘要：

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.041
• 作为产物：
  描述：

  (E)-5,7,11-Trimethyl-7-vinyl-dodeca-1,5,10-trien-3-ol 以 neat (no solvent) 为溶剂， 以46%的产率得到5,9,13-trimethyl-4,8,12-tetradecatrienal
  参考文献：
  名称：

  基于双烯丙基醚系统[2,3] -wittig重排的新σ序列：导致不饱和羰基化合物的烯丙基部分区域控制的cc键形成的一般方法

  摘要：

  描述了由不对称双烯丙基醚（1）到1,5-二烯-3-醇（2）的区域控制[2,3] -Wittig重排触发的四个新的sigmatropic序列，它们提供了独特的区域控制方法具有令人感兴趣的分子框架的各种不饱和羰基化合物的合成。新开发的序列包括[2,3] -Wittig-Claisen，串联[2,3] -Wittig-oxy-Cope，串联oxy-Cope-Claisen和串联oxy-Cope-Cope序列。

  DOI：

  10.1016/s0040-4020(01)90580-0

文献信息

• New sigmatropic sequences based on the [2,3] Wittig rearrangement of bis(allylic) ethers. Regiocontrolled joining reactions of two or three allylic moieties leading to unsaturated carbonyl compounds
  作者：K. Mikami、S. Taya、T. Nakai、Y. Fujita

  DOI：10.1021/jo00339a051

  日期：1981.12
• New sigmatropic sequences based on the [2,3]-wittig rearrangement of the bis-allylic ether system
  作者：Kōichi Mikami、Naoyuki Kishi、Takeshi Nakai、Yoshiji Fujita

  DOI：10.1016/s0040-4020(01)90580-0

  日期：1986.1

  Four new sigmatropic sequences triggered by the regiocontrolled [2,3]-Wittig rearrangement of unsymmetrical bis-allylic ethers (1) to the l,5-dien-3-ols (2) arc described, which provide unique, regiocontrolled methods for the synthesis of a wide variety of unsaturated carbonyl compounds possessing interesting molecular frameworks. The newly developed sequences include the [2,3]-Wittig-Claisen, the

  描述了由不对称双烯丙基醚（1）到1,5-二烯-3-醇（2）的区域控制[2,3] -Wittig重排触发的四个新的sigmatropic序列，它们提供了独特的区域控制方法具有令人感兴趣的分子框架的各种不饱和羰基化合物的合成。新开发的序列包括[2,3] -Wittig-Claisen，串联[2,3] -Wittig-oxy-Cope，串联oxy-Cope-Claisen和串联oxy-Cope-Cope序列。
• Total syntheses of the squalene-derived halogenated polyethers ent -dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades
  作者：Brian S. Underwood、Jessica Tanuwidjaja、Sze-Sze Ng、Timothy F. Jamison

  DOI：10.1016/j.tet.2013.04.041

  日期：2013.6

  Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. (C) 2013 Elsevier Ltd. All rights reserved.