tert-butyl 4-methylpent-4-enoate | 1338575-63-5

• 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: tert-butyl 4-methylpent-4-enoate
• CAS: 1338575-63-5
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: IGVOOVOMGZONNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  tert-butyl 4-methylpent-4-enoate 、 (E)-3-methylbut-3-en-2-one O-pivaloyl oxime 在 六氟异丙醇 、 [Cp*^CF3Rh(MeCN)₃](SbF₆)₂ 、 cesium acetate 作用下， 反应 12.0h， 以92%的产率得到(R)-tert-butyl 3-(3,5,6-trimethyl-2,3-dihydropyridin-3-yl)propanoate
  参考文献：
  名称：

  Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C–H Activation

  摘要：

  alpha,beta-Unsaturated - oxime pivalates are proposed to undergo reversible C(sp(2))-H insertion with cationic Rh (III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to. convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.

  DOI：

  10.1021/jacs.5b04946
• 作为产物：
  描述：

  4-甲基戊-4-烯腈 在 二碳酸二叔丁酯 、 氯化镁 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 生成 tert-butyl 4-methylpent-4-enoate
  参考文献：
  名称：

  Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C–H Activation

  摘要：

  alpha,beta-Unsaturated - oxime pivalates are proposed to undergo reversible C(sp(2))-H insertion with cationic Rh (III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to. convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.

  DOI：

  10.1021/jacs.5b04946

文献信息

• Copper-Catalyzed Iminoiodane-Mediated Aminolactonization of Olefins: Application to the Synthesis of 5,5-Disubstituted Butyrolactones
  作者：Delphine Karila、Loïc Leman、Robert H. Dodd

  DOI：10.1021/ol202436a

  日期：2011.11.4

  A copper(I)-catalyzed reaction of a variety of 4-aryl-pent-4-enoates with nosyliminolodane generated in situ provides the corresponding 5-aryl-5. nosylamidomethylbutyrolactones. The reaction presumably proceeds via an aziridine intermediate, which could be isolated in one case.
• Expedient Access to 2,3-Dihydropyridines from Unsaturated Oximes by Rh(III)-Catalyzed C–H Activation
  作者：Fedor Romanov-Michailidis、Kassandra F. Sedillo、Jamie M. Neely、Tomislav Rovis

  DOI：10.1021/jacs.5b04946

  日期：2015.7.22

  alpha,beta-Unsaturated - oxime pivalates are proposed to undergo reversible C(sp(2))-H insertion with cationic Rh (III) complexes to furnish five-membered metallacycles. In the presence of 1,1-disubstituted olefins, these species participate in irreversible migratory insertion to give, after reductive elimination, 2,3-dihydropyridine products in good yields. Catalytic hydrogenation can then be used to. convert these molecules into piperidines, which are important structural components of numerous pharmaceuticals.