[2'E,6'E]-5-[8'-acetoxy-2',6'-dimethylocta-2',6'-dienyl]-3-methyl-2(5H)-furanone | 133727-03-4

• 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: [2'E,6'E]-5-[8'-acetoxy-2',6'-dimethylocta-2',6'-dienyl]-3-methyl-2(5H)-furanone
• 英文别名: [(2E,6E)-3,7-dimethyl-8-(4-methyl-5-oxo-2H-furan-2-yl)octa-2,6-dienyl] acetate
• CAS: 133727-03-4
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: RWEGFTQUMKMZJU-SWZPTJTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  [2'E,6'E]-5-[8'-acetoxy-2',6'-dimethylocta-2',6'-dienyl]-3-methyl-2(5H)-furanone 在 三(2-氯乙基)胺 、 偶氮二甲酸二异丙酯 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 7.0h， 生成 [2E,6E]-3,7-dimethyl-8-(4'-methyl-2'-furanyl)-2,6-octadienyl azide
  参考文献：
  名称：

  A Concise Synthesis of Siphonodictidine

  摘要：

  Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoroacetate-induced alkylation of 6 with omega-bromogeranyl acetate 7 gave the key gamma-lactone intermediate 8, which on subsequent reduction, conversion of the hydroxyl into the amino group, and amidination afforded siphonodictidine (1) in an overall yield of 25.7% from 6.

  DOI：

  10.1021/np0400860
• 作为产物：
  描述：

  3-甲基-2(5H)-呋喃酮 在 AgOCOF₃ 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 [2'E,6'E]-5-[8'-acetoxy-2',6'-dimethylocta-2',6'-dienyl]-3-methyl-2(5H)-furanone
  参考文献：
  名称：

  A Concise Synthesis of Siphonodictidine

  摘要：

  Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoroacetate-induced alkylation of 6 with omega-bromogeranyl acetate 7 gave the key gamma-lactone intermediate 8, which on subsequent reduction, conversion of the hydroxyl into the amino group, and amidination afforded siphonodictidine (1) in an overall yield of 25.7% from 6.

  DOI：

  10.1021/np0400860

文献信息

• JEFFORD, CHARLES W.;HUANG, PING-ZHONG;ROSSIER, JEAN-CLAUDE;SLEDESKI, ADAM+, SYNLETT.,(1990) N2, C. 745-746
  作者：JEFFORD, CHARLES W.、HUANG, PING-ZHONG、ROSSIER, JEAN-CLAUDE、SLEDESKI, ADAM+

  DOI：——

  日期：——
• A Concise Synthesis of Siphonodictidine
  作者：Charles W. Jefford、Jean-Claude Rossier、John Boukouvalas、Adam W. Sledeski、Ping-Zhong Huang

  DOI：10.1021/np0400860

  日期：2004.8.1

  Siphonodictidine (1) has been synthesized for the first time in a concise and regiocontrolled manner by using 2-(tert-butyldimethylsiloxy)-3-methylfuran (6) as the crucial building block. The silver trifluoroacetate-induced alkylation of 6 with omega-bromogeranyl acetate 7 gave the key gamma-lactone intermediate 8, which on subsequent reduction, conversion of the hydroxyl into the amino group, and amidination afforded siphonodictidine (1) in an overall yield of 25.7% from 6.