(Z)-4-Methyl-hex-3-en-5-yn-2-ol | 101011-92-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-Methyl-hex-3-en-5-yn-2-ol
• 英文别名: 4-methylhex-3-en-5-yn-2-ol
• CAS: 101011-92-1
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: KWBZOHFUMTYBNC-UHFFFAOYSA-N

物化性质

• 沸点：
  71.5-72 °C(Press: 20 Torr)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-4-Methyl-hex-3-en-5-yn-2-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 5-硝基-2-(4-硝基苯基)-1H-咪唑
  参考文献：
  名称：

  Carbonylation of Alkynyl Epoxides:  Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives

  摘要：

  The carbonylation of alkynyl oxiranes catalyzed by (MePh2)(4)Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethanol derivatives, 4,5-dihydrofuran-3-ol derivatives are obtained stereoselectively. These products arise from the spontaneous cyclization of a dihydroxyallenyl ester intermediate.

  DOI：

  10.1021/jo971303n
• 作为产物：
  描述：

  3-戊烯-2-酮 在 硫酸 作用下， 以 乙醚 为溶剂， 生成 (Z)-4-Methyl-hex-3-en-5-yn-2-ol
  参考文献：
  名称：

  Carbonylation of Alkynyl Epoxides:  Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives

  摘要：

  The carbonylation of alkynyl oxiranes catalyzed by (MePh2)(4)Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethanol derivatives, 4,5-dihydrofuran-3-ol derivatives are obtained stereoselectively. These products arise from the spontaneous cyclization of a dihydroxyallenyl ester intermediate.

  DOI：

  10.1021/jo971303n

文献信息

• Synthesis of N-Acyl Pyrroles and Isoindoles from Oxime Ester Precursors via Transition-Metal-Catalyzed Iminocarboxylation
  作者：Daesung Lee、Siyuan Su

  DOI：10.1055/s-0042-1751377

  日期：——

  3-enyne and an ortho-alkynylarene moiety, followed by a spontaneous O→N acyl migration of the enol carboxylate intermediate to generate N-acyl pyrroles and isoindoles. The reaction scope for pyrrole synthesis is general, whereas the formation of isoindoles has a relatively narrow scope because of their instability.

  我们描述了 Pt(II)- 和 Fe(III)- 催化的与 1,3-烯炔和邻-炔芳烃部分共轭的肟酯的亚氨基羧化反应，随后烯醇羧酸酯中间体的自发 O→N 酰基迁移生成N-酰基吡咯和异吲哚。吡咯合成的反应范围一般，而异吲哚的形成则因其不稳定性而范围相对狭窄。
• 10.1021/acs.orglett.4c01916
  作者：Lin, Tao-Yan、Li, Meng-Die、Wang, Rui、Wang, Xinru

  DOI：10.1021/acs.orglett.4c01916

  日期：——

  space for the development of chiral anthrone derivatives is largely limited. By utilizing the potential of the copper-catalyzed remote asymmetric yne-allylic substitution reaction, we describe the first example of copper-catalyzed highly regio- and enantioselective remote yne-allylic substitution on various yne-allylic esters with anthrones under a mild reaction condition, which afforded a range of enantioenriched

  蒽酮是许多天然产物和药物化学品中的关键结构基序。然而，由于其独特的三环芳香结构，手性蒽酮衍生物的开发合成空间受到很大限制。通过利用铜催化远程不对称炔烯丙基取代反应的潜力，我们描述了铜催化在温和反应条件下用蒽酮对各种炔烯丙酯进行高度区域和对映选择性远程炔烯丙基取代的第一个例子，它提供了一系列对映体富集的 1,3-烯炔，在 51 个实例中表现出广泛的官能团耐受性。
• Carbonylation of Alkynyl Epoxides:  Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives
  作者：Marcelo E. Piotti、Howard Alper

  DOI：10.1021/jo971303n

  日期：1997.11.1

  The carbonylation of alkynyl oxiranes catalyzed by (MePh2)(4)Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethanol derivatives, 4,5-dihydrofuran-3-ol derivatives are obtained stereoselectively. These products arise from the spontaneous cyclization of a dihydroxyallenyl ester intermediate.