2-methylene-undec-9-ynoic acid (S)-1-methylallyl ester | 292643-09-5

• 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: 2-methylene-undec-9-ynoic acid (S)-1-methylallyl ester
• 英文别名: [(2S)-but-3-en-2-yl] 2-methylideneundec-9-ynoate
• CAS: 292643-09-5
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: FCCZQZYABZLEQH-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methylene-undec-9-ynoic acid (S)-1-methylallyl ester 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以70%的产率得到5-(S)-methyl-3-(non-7-ynyl)-(5H)-furan-2-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
• 作为产物：
  描述：

  1-碘代丙炔 、 2-(bromomethyl)acrylic acid (S)-1-methylallyl ester 、 在 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 15.25h， 以70%的产率得到2-methylene-undec-9-ynoic acid (S)-1-methylallyl ester
  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%.