(2S)-2-methyl-4-[14-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]tetradec-7-ynyl]-2H-furan-5-one | 292643-11-9

• 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: (2S)-2-methyl-4-[14-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]tetradec-7-ynyl]-2H-furan-5-one
• CAS: 292643-11-9
• 化学式: C₂₄H₃₄O₄
• 分子量: 386.532
• InChiKey: AXEHGKJKUFZUEI-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (2S)-2-methyl-4-[14-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]tetradec-7-ynyl]-2H-furan-5-one 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 乙醇 、 正己烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.17h， 以94%的产率得到13,13'-Dehydrohomoancepsenolide
  参考文献：
  名称：

  Concise Synthesis of (S,S)-(+)-Dehydrohomoancepsenolide

  摘要：

  [GRAPHICS]A concise total synthesis of the bis-butenolide 3 in optically active form is reported. Key steps are a zinc mediated "three component coupling" with formation of dienyne 9 which undergoes ring closing metathesis (RCM) on treatment with (PCy3)(2)Cl2Ru=CHPh. Dimerization of the resulting butenolide 11 is then achieved via alkyne metathesis using (tBuO)(3)W=CCMe3 as the catalyst. A Lindlar reduction completes this synthesis which delivers product 3 in only five steps with an overall yield of 25%.

  DOI：

  10.1021/ol006122d
• 作为产物：
  描述：

  2-methylene-undec-9-ynoic acid (S)-1-methylallyl ester 在 Tris(t-butoxy)(2,2-dimethylpropylidyne)tungsten(VI), 98% Schrock Alkyne Metathesis Catalyst 、 Grubbs catalyst first generation 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 45.0h， 生成 (2S)-2-methyl-4-[14-[(2S)-2-methyl-5-oxo-2H-furan-4-yl]tetradec-7-ynyl]-2H-furan-5-one
  参考文献：
  名称：

  Concise Synthesis of (S,S)-(+)-Dehydrohomoancepsenolide

  摘要：

  [GRAPHICS]A concise total synthesis of the bis-butenolide 3 in optically active form is reported. Key steps are a zinc mediated "three component coupling" with formation of dienyne 9 which undergoes ring closing metathesis (RCM) on treatment with (PCy3)(2)Cl2Ru=CHPh. Dimerization of the resulting butenolide 11 is then achieved via alkyne metathesis using (tBuO)(3)W=CCMe3 as the catalyst. A Lindlar reduction completes this synthesis which delivers product 3 in only five steps with an overall yield of 25%.

  DOI：

  10.1021/ol006122d

文献信息

• Concise Synthesis of (<i>S,S</i>)-(+)-Dehydrohomoancepsenolide
  作者：Alois Fürstner、Thorsten Dierkes

  DOI：10.1021/ol006122d

  日期：2000.8.1

  [GRAPHICS]A concise total synthesis of the bis-butenolide 3 in optically active form is reported. Key steps are a zinc mediated "three component coupling" with formation of dienyne 9 which undergoes ring closing metathesis (RCM) on treatment with (PCy3)(2)Cl2Ru=CHPh. Dimerization of the resulting butenolide 11 is then achieved via alkyne metathesis using (tBuO)(3)W=CCMe3 as the catalyst. A Lindlar reduction completes this synthesis which delivers product 3 in only five steps with an overall yield of 25%.