2-methyldodec-1-en-3-yn-5-yl but-3-enoate | 1385017-84-4

• 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-methyldodec-1-en-3-yn-5-yl but-3-enoate
• CAS: 1385017-84-4
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: LARNEBKMTQPMFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 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：

  一氧化碳 、 2-methyldodec-1-en-3-yn-5-yl but-3-enoate 在 di(rhodium)tetracarbonyl dichloride 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-2-methyl-5-octylidene-4-oxocyclopent-1-en-1-yl but-3-enoate 、 (Z)-2-methyl-5-octylidene-4-oxocyclopent-1-en-1-yl but-3-enoate
  参考文献：
  名称：

  Diastereoselective [4 + 1] Cycloaddition of Alkenyl Propargyl Acetates with CO Catalyzed by [RhCl(CO)₂]₂

  摘要：

  A class of alkenyl propargyl acetates, RCH(OAc)C CC(CH3)=CH2 (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.

  DOI：

  10.1021/jo3009403
• 作为产物：
  描述：

  正辛醛 、 2-甲基-1-丁烯-3-炔 在 4-二甲氨基吡啶 、 正丁基锂 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-methyldodec-1-en-3-yn-5-yl but-3-enoate
  参考文献：
  名称：

  Diastereoselective [4 + 1] Cycloaddition of Alkenyl Propargyl Acetates with CO Catalyzed by [RhCl(CO)₂]₂

  摘要：

  A class of alkenyl propargyl acetates, RCH(OAc)C CC(CH3)=CH2 (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.

  DOI：

  10.1021/jo3009403

文献信息

• Diastereoselective [4 + 1] Cycloaddition of Alkenyl Propargyl Acetates with CO Catalyzed by [RhCl(CO)₂]₂
  作者：Wei Chen、Jia-Hui Tay、Xiao-Qi Yu、Lin Pu

  DOI：10.1021/jo3009403

  日期：2012.7.20

  A class of alkenyl propargyl acetates, RCH(OAc)C CC(CH3)=CH2 (5), are found to undergo [4 + 1] cycloaddition with CO (1 atm) in the presence of [RhCl(CO)(2)](2) in refluxing 1,2-dichloroethane to give cyclopentenones (6) in good yields. It has been demonstrated that, when the R group of 5 is a phenyl group bearing o-electron-withdrawing substituents up to 10:1 diastereoselectivity and 96% yield can be achieved for the [4 + 1] cycloaddition. This process provides a convenient method to construct highly functionalized cyclopentenones that are useful in organic synthesis.