methyl (E,2S,3S,4R)-3-hydroxy-2,4,6-trimethyloct-6-enoate | 1027073-57-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (E,2S,3S,4R)-3-hydroxy-2,4,6-trimethyloct-6-enoate
• CAS: 1027073-57-9
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: GKAPICKFCKCHML-MHVQYWQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E,2S,3S,4R)-3-hydroxy-2,4,6-trimethyloct-6-enoate 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 methyl hemibourgeanate 、 methyl 6-epihemibourgeanate
  参考文献：
  名称：

  Synthesis of the Aliphatic Depside (+)-Bourgeanic Acid

  摘要：

  The lichen metabolite (+)-bourgeanic acid (1) was synthesized in 12 steps and 3.4% overall yield from (R)-2-methyl-1-iodobutane (53) by a sequence which confirmed that this aliphatic depside is the self-esterification product of (2S,3S,4R,6R)-2,4,6-trimethyl-3-hydroxyoctanoic acid. Alkylation of the enolate of (S)-N-propionylprolinol (48) with 53 gave the amide 60 which was transformed to (2R,4R)-2,4-dimethylhexanal (4). The latter was reacted with the crotylboronate 68, prepared from (S,S)-(-)-diisopropyltartrate, to afford (3R,4S,5R,7R)-3,5,7-trimethyl-1-nonen-4-ol (65) as the major diastereomer. Protection followed by ozonolysis and oxidation furnished (-)-hemibourgeanic acid (2). The beta-lactone 73 derived from 2 was used to acylate 65, and the resulting ester 74 was subjected to oxidative ozonolysis to yield (+)-1.

  DOI：

  10.1021/jo00091a022
• 作为产物：
  描述：

  (2'S,4S)-(E)-3-(2',4'-dimethyl-4'-hexenoyl)-4-isopropyl-1,3-oxazolidin-2-one 在 lithium aluminium tetrahydride 、 cerium(III) chloride 、 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 methyl (E,2S,3S,4R)-3-hydroxy-2,4,6-trimethyloct-6-enoate
  参考文献：
  名称：

  Synthesis of the Aliphatic Depside (+)-Bourgeanic Acid

  摘要：

  The lichen metabolite (+)-bourgeanic acid (1) was synthesized in 12 steps and 3.4% overall yield from (R)-2-methyl-1-iodobutane (53) by a sequence which confirmed that this aliphatic depside is the self-esterification product of (2S,3S,4R,6R)-2,4,6-trimethyl-3-hydroxyoctanoic acid. Alkylation of the enolate of (S)-N-propionylprolinol (48) with 53 gave the amide 60 which was transformed to (2R,4R)-2,4-dimethylhexanal (4). The latter was reacted with the crotylboronate 68, prepared from (S,S)-(-)-diisopropyltartrate, to afford (3R,4S,5R,7R)-3,5,7-trimethyl-1-nonen-4-ol (65) as the major diastereomer. Protection followed by ozonolysis and oxidation furnished (-)-hemibourgeanic acid (2). The beta-lactone 73 derived from 2 was used to acylate 65, and the resulting ester 74 was subjected to oxidative ozonolysis to yield (+)-1.

  DOI：

  10.1021/jo00091a022

文献信息

• Synthesis of the Aliphatic Depside (+)-Bourgeanic Acid
  作者：James D. White、Alan T. Johnson

  DOI：10.1021/jo00091a022

  日期：1994.6

  The lichen metabolite (+)-bourgeanic acid (1) was synthesized in 12 steps and 3.4% overall yield from (R)-2-methyl-1-iodobutane (53) by a sequence which confirmed that this aliphatic depside is the self-esterification product of (2S,3S,4R,6R)-2,4,6-trimethyl-3-hydroxyoctanoic acid. Alkylation of the enolate of (S)-N-propionylprolinol (48) with 53 gave the amide 60 which was transformed to (2R,4R)-2,4-dimethylhexanal (4). The latter was reacted with the crotylboronate 68, prepared from (S,S)-(-)-diisopropyltartrate, to afford (3R,4S,5R,7R)-3,5,7-trimethyl-1-nonen-4-ol (65) as the major diastereomer. Protection followed by ozonolysis and oxidation furnished (-)-hemibourgeanic acid (2). The beta-lactone 73 derived from 2 was used to acylate 65, and the resulting ester 74 was subjected to oxidative ozonolysis to yield (+)-1.