(-)-hemibourgeanic acid β-lactone | 62856-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (-)-hemibourgeanic acid β-lactone
• 英文别名: (1'R,3R,3'R)-3-methyl-4-(1',3'-dimethylpentyl)-2-oxetanone；(3S,4S)-3-methyl-4-[(2R,4R)-4-methylhexan-2-yl]oxetan-2-one
• CAS: 62856-67-1
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: UATPZIBZBLZGIV-IMSYWVGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (-)-hemibourgeanic acid β-lactone 在 正丁基锂 、 双氧水 、 臭氧 作用下， 生成 (2S,3S,4R,6R)-3-hydroxy-2,4,6-trimethyl-octanoic acid (1S,2R,4R)-1-((S)-1-carboxyethyl)-2,4-dimethyl-hexyl ester
  参考文献：
  名称：

  Synthesis of the lichen metabolite (+)-bourgeanic acid and conformational analysis of its dilactone

  摘要：

  DOI：

  10.1021/jo00311a009
• 作为产物：
  描述：

  (2E)-1-溴-2-甲基-2-丁烯 在 Rh(norbornadiene)(bis(diphenylphosphino)butane)(+)BF4(-) 吡啶 、 2,6-二甲基吡啶 、 chromium dichloride 、 sodium chlorite 、 lithium aluminium tetrahydride 、 2-甲基-2-丁烯 、 草酰氯 、 二甲基硫 、 氢氟酸 、 氢气 、 臭氧 、 二甲基亚砜 、 三乙胺 、 苯磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 89.5h， 生成 (-)-hemibourgeanic acid β-lactone
  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

• WHITE, JAMES D.;JOHNSON, ALAN T., J. ORG. CHEM., 55,(1990) N4, C. 5938-5940
  作者：WHITE, JAMES D.、JOHNSON, ALAN T.

  DOI：——

  日期：——
• Synthesis of the lichen metabolite (+)-bourgeanic acid and conformational analysis of its dilactone
  作者：James D. White、Alan T. Johnson

  DOI：10.1021/jo00311a009

  日期：1990.11
• 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.