ethyl (E)-2-methyl-2-penten-4-ynoate | 548757-28-4

• 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: ethyl (E)-2-methyl-2-penten-4-ynoate
• 英文别名: ethyl (E)-2-methylpent-2-en-4-ynoate；ethyl (2E)-2-methylpent-2-en-4-ynoate
• CAS: 548757-28-4
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: GNTNWQISZABCHU-VOTSOKGWSA-N

物化性质

• 沸点：
  169.0±23.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 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 (E)-2-methyl-2-penten-4-ynoate 在 四(三苯基膦)钯 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以72%的产率得到(2E,8E)-2,9-Dimethyl-deca-2,8-diene-4,6-diynedioic acid diethyl ester
  参考文献：
  名称：

  Highly Satisfactory Alkynylation of Alkenyl Halides via Pd-Catalyzed Cross-Coupling with Alkynylzincs and Its Critical Comparison with the Sonogashira Alkynylation

  摘要：

  [GRAPHICS]The Pd-catalyzed alkynylation of various alkenyl halides and triflates with alkynylzincs proceeds well even with alkynyl derivatives containing electron-withdrawing groups. The reaction appears to be highly general. Noteworthy is that the corresponding Sonogashira reactions under various reported conditions are significantly less satisfactory in all cases performed in this study.

  DOI：

  10.1021/ol030010f
• 作为产物：
  描述：

  ethyl (E)-2-methyl-5-(trimethylsilyl)pent-2-en-4-ynoate 在 四丁基氟化铵 、 三乙胺 、 氯化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.33h， 以92%的产率得到ethyl (E)-2-methyl-2-penten-4-ynoate
  参考文献：
  名称：

  Total Synthesis of the Hsp90 Inhibitor Geldanamycin

  摘要：

  An enantioselective synthesis of the Hsp90 inhibitor geldanamycin was achieved in 20 linear steps and 2.0% overall yield from 2-methoxyhydroquinone. The synthesis is highlighted by a regio- and stereoselective hydroboration reaction; a Sc(OTf)(3)/Et(3)SiH-mediated pyran ring-opening reaction; an enantioselective crotylation to simultaneously install the C8-C9 (E)-trisubstituted olefin, the C10 and C11 stereocenters; a chelation-controlled asymmetric metallated acetylide addition; and an intramolecular copper(I)-mediated aryl amidation reaction to close the 19-membered macrolactam.

  DOI：

  10.1021/ol800749w

文献信息

• Highly Satisfactory Alkynylation of Alkenyl Halides via Pd-Catalyzed Cross-Coupling with Alkynylzincs and Its Critical Comparison with the Sonogashira Alkynylation
  作者：Ei-ichi Negishi、Mingxing Qian、Fanxing Zeng、Luigi Anastasia、David Babinski

  DOI：10.1021/ol030010f

  日期：2003.5.1

  [GRAPHICS]The Pd-catalyzed alkynylation of various alkenyl halides and triflates with alkynylzincs proceeds well even with alkynyl derivatives containing electron-withdrawing groups. The reaction appears to be highly general. Noteworthy is that the corresponding Sonogashira reactions under various reported conditions are significantly less satisfactory in all cases performed in this study.
• Total Synthesis of the Hsp90 Inhibitor Geldanamycin
  作者：Hua-Li Qin、James S. Panek

  DOI：10.1021/ol800749w

  日期：2008.6.1

  An enantioselective synthesis of the Hsp90 inhibitor geldanamycin was achieved in 20 linear steps and 2.0% overall yield from 2-methoxyhydroquinone. The synthesis is highlighted by a regio- and stereoselective hydroboration reaction; a Sc(OTf)(3)/Et(3)SiH-mediated pyran ring-opening reaction; an enantioselective crotylation to simultaneously install the C8-C9 (E)-trisubstituted olefin, the C10 and C11 stereocenters; a chelation-controlled asymmetric metallated acetylide addition; and an intramolecular copper(I)-mediated aryl amidation reaction to close the 19-membered macrolactam.