(3S,4R,5R,7R)-3,5,7-trimethyl-1-nonen-4-ol

• 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: (3S,4R,5R,7R)-3,5,7-trimethyl-1-nonen-4-ol
• 英文别名: (3S,4R,5R,7R)-3,5,7-trimethylnon-1-en-4-ol
• 化学式: C₁₂H₂₄O
• 分子量: 184.322
• InChiKey: MRFPSPKNLTWPJV-KXNHARMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (3S,4R,5R,7R)-3,5,7-trimethyl-1-nonen-4-ol 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以1.03 g的产率得到(3S,4R,5R,7R)-4-O-(tert-butyl-dimethylsilyl)-3,5,7-trimethyl-1-nonen-4-ol
  参考文献：
  名称：

  高草甘膦A的合成研究：（2 R，3 R，4 R，6 R）-3-羟基-2,4,6-三甲基辛酸的立体选择性合成

  摘要：

  （2 R，3 R，4 R，6 R）-3-羟基-2,4,6-三甲基辛酸的高效且高度立体控制的合成，该酸将高草甘膦A的N末端酰化，从碘乙烷和（S，S）-伪麻黄碱丙酰胺开始设计9个步骤，平均总收率36％。所得β-羟基酸与天然片段的1 H和13 C NMR和旋光数据的比较明确验证了构型分配为（2 R，3 R，4 R，6 R）。

  DOI：

  10.1016/j.tet.2009.02.069
• 作为产物：
  描述：

  (2E)-1-溴-2-甲基-2-丁烯 在 Rh(norbornadiene)(bis(diphenylphosphino)butane)(+)BF4(-) chromium dichloride 、 lithium aluminium tetrahydride 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.25h， 生成 (3S,4R,5R,7R)-3,5,7-trimethyl-1-nonen-4-ol
  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.
• Synthetic studies on homophymine A: stereoselective synthesis of (2R,3R,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid
  作者：Filomena Bellotta、Maria Valeria D'Auria、Valentina Sepe、Angela Zampella

  DOI：10.1016/j.tet.2009.02.069

  日期：2009.5

  highly stereocontrolled synthesis of (2R,3R,4R,6R)-3-hydroxy-2,4,6-trimethyloctanoic acid, the β-hydroxy acid unit that acylates the N-terminus of homophymine A, has been devised starting from iodoethane and (S,S)-pseudoephedrine propionamide in 9 steps and 36% average overall yield. Comparison of the 1H and 13C NMR and optical rotation data of the resulting β-hydroxy acid with the natural fragment

  （2 R，3 R，4 R，6 R）-3-羟基-2,4,6-三甲基辛酸的高效且高度立体控制的合成，该酸将高草甘膦A的N末端酰化，从碘乙烷和（S，S）-伪麻黄碱丙酰胺开始设计9个步骤，平均总收率36％。所得β-羟基酸与天然片段的1 H和13 C NMR和旋光数据的比较明确验证了构型分配为（2 R，3 R，4 R，6 R）。