Hexanoic acid (E)-3-(5-oxo-2,5-dihydro-furan-3-yl)-allyl ester | 184780-68-5

• 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: Hexanoic acid (E)-3-(5-oxo-2,5-dihydro-furan-3-yl)-allyl ester
• 英文别名: [(E)-3-(5-oxo-2H-furan-3-yl)prop-2-enyl] hexanoate
• CAS: 184780-68-5
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: HUYVHPMTCVVOFV-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Hexanoic acid (E)-3-(5-oxo-2,5-dihydro-furan-3-yl)-allyl ester 在 甲基磺酰胺 、 AD-mix-β 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以72%的产率得到4-(1,2-dihydroxy-5-oxodecyl)furan-2(5H)-one
  参考文献：
  名称：

  Enantioselective Syntheses of Syributin 1 and Novel C-Glycosidic Elicitors Syringolides 1 and 2

  摘要：

  Concise enantioselective syntheses of syributin 1 (3) and the novel nonproteinaceous C-glycosidic elicitors syringolides 1 and 2 (1 and 2, respectively), isolated from Pseudomonas syringae pv. tomato, are described. Syributin 1 was synthesized in one step by the Sharpless catalytic asymmetric dihydroxylation (AD reaction) of (1'E)-3-(3'-(octanoyloxy)-1'-propenyl)but-2-en-4-olide (13) in 72% yield with >98% ee. Furthermore, alkylation of (1'R,2'R)-3-[1'-(tert-butyldimethylsiloxy)-2,3'- (isopropylidenedioxy)propyl]but-2-en-4-olide (20), prepared from (1'E)-3-[3'-(tert-butyldimethylsiloxy)-1'-propenyl]but-2-en-4-olide (11) by the AD reaction, with hexanal or octanal by Jefford's procedure at the a position to the lactone carbonyl group gave adduct 21 or 22 in good yield. Oxidation of 21 or 2;2, followed by removal of the protecting groups, provided syringolide 1 or 2, respectively.

  DOI：

  10.1021/jo961362l
• 作为产物：
  描述：

  3-[(E)-3-[tert-butyl(dimethyl)silyl]oxyprop-1-enyl]-2H-furan-5-one 在 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 Hexanoic acid (E)-3-(5-oxo-2,5-dihydro-furan-3-yl)-allyl ester
  参考文献：
  名称：

  Enantioselective Syntheses of Syributin 1 and Novel C-Glycosidic Elicitors Syringolides 1 and 2

  摘要：

  Concise enantioselective syntheses of syributin 1 (3) and the novel nonproteinaceous C-glycosidic elicitors syringolides 1 and 2 (1 and 2, respectively), isolated from Pseudomonas syringae pv. tomato, are described. Syributin 1 was synthesized in one step by the Sharpless catalytic asymmetric dihydroxylation (AD reaction) of (1'E)-3-(3'-(octanoyloxy)-1'-propenyl)but-2-en-4-olide (13) in 72% yield with >98% ee. Furthermore, alkylation of (1'R,2'R)-3-[1'-(tert-butyldimethylsiloxy)-2,3'- (isopropylidenedioxy)propyl]but-2-en-4-olide (20), prepared from (1'E)-3-[3'-(tert-butyldimethylsiloxy)-1'-propenyl]but-2-en-4-olide (11) by the AD reaction, with hexanal or octanal by Jefford's procedure at the a position to the lactone carbonyl group gave adduct 21 or 22 in good yield. Oxidation of 21 or 2;2, followed by removal of the protecting groups, provided syringolide 1 or 2, respectively.

  DOI：

  10.1021/jo961362l

文献信息

• Enantioselective Syntheses of Syributin 1 and Novel C-Glycosidic Elicitors Syringolides 1 and 2
  作者：Toshio Honda、Hirotake Mizutani、Kazuo Kanai

  DOI：10.1021/jo961362l

  日期：1996.1.1

  Concise enantioselective syntheses of syributin 1 (3) and the novel nonproteinaceous C-glycosidic elicitors syringolides 1 and 2 (1 and 2, respectively), isolated from Pseudomonas syringae pv. tomato, are described. Syributin 1 was synthesized in one step by the Sharpless catalytic asymmetric dihydroxylation (AD reaction) of (1'E)-3-(3'-(octanoyloxy)-1'-propenyl)but-2-en-4-olide (13) in 72% yield with >98% ee. Furthermore, alkylation of (1'R,2'R)-3-[1'-(tert-butyldimethylsiloxy)-2,3'- (isopropylidenedioxy)propyl]but-2-en-4-olide (20), prepared from (1'E)-3-[3'-(tert-butyldimethylsiloxy)-1'-propenyl]but-2-en-4-olide (11) by the AD reaction, with hexanal or octanal by Jefford's procedure at the a position to the lactone carbonyl group gave adduct 21 or 22 in good yield. Oxidation of 21 or 2;2, followed by removal of the protecting groups, provided syringolide 1 or 2, respectively.