ethyl 6-bromo-2,2-dimethylhex-4-ynoate | 1140383-31-8

• 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: ethyl 6-bromo-2,2-dimethylhex-4-ynoate
• CAS: 1140383-31-8
• 化学式: C₁₀H₁₅BrO₂
• 分子量: 247.132
• InChiKey: JVGHAQUHGQSLOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 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：

  ethyl 6-bromo-2,2-dimethylhex-4-ynoate 、 3-苯基-2-丙炔-1-醇 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.0h， 以78%的产率得到ethyl 2,2-dimethyl-6-(3-phenylprop-2-ynyloxy)hex-4-ynoate
  参考文献：
  名称：

  Synthesis of Unique Scaffolds via Diels−Alder Cycloadditions of Tetrasubstituted Cyclohexadienes

  摘要：

  Diels-Alder cycloadditions of highly substituted cyclohexadienes derived from rhodium-mediated [2 + 2 + 2] cyclizations are reported. Reactive heterodienophiles, including singlet oxygen (O-1(2)), 4-substituted-1,2,4-triazoline-3,5-diones (TADs), and aryl- and acylnitroso compounds were employed, yielding novel heterocyclic products.

  DOI：

  10.1021/ol100318f
• 作为产物：
  描述：

  1,4-二溴-2-丁炔 、 异丁酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到ethyl 6-bromo-2,2-dimethylhex-4-ynoate
  参考文献：
  名称：

  Intramolecular Rhodium-Catalyzed [2+2+2] Cyclizations of Diynes with Enones

  摘要：

  The Rh(I)-catalyzed inter- and intramolecular [2+2+2] cyclization of diynes with alpha,beta-unsaturated enones proceeds with microwave promotion in good yields. This chemistry was applied to the synthesis of (-)-alcyopterosin I.

  DOI：

  10.1021/jo9001678

文献信息

• Synthesis of Unique Scaffolds via Diels−Alder Cycloadditions of Tetrasubstituted Cyclohexadienes
  作者：Amanda L. Jones、John K. Snyder

  DOI：10.1021/ol100318f

  日期：2010.4.2

  Diels-Alder cycloadditions of highly substituted cyclohexadienes derived from rhodium-mediated [2 + 2 + 2] cyclizations are reported. Reactive heterodienophiles, including singlet oxygen (O-1(2)), 4-substituted-1,2,4-triazoline-3,5-diones (TADs), and aryl- and acylnitroso compounds were employed, yielding novel heterocyclic products.
• Intramolecular Rhodium-Catalyzed [2+2+2] Cyclizations of Diynes with Enones
  作者：Amanda L. Jones、John K. Snyder

  DOI：10.1021/jo9001678

  日期：2009.4.3

  The Rh(I)-catalyzed inter- and intramolecular [2+2+2] cyclization of diynes with alpha,beta-unsaturated enones proceeds with microwave promotion in good yields. This chemistry was applied to the synthesis of (-)-alcyopterosin I.