(Z)-3-methylnon-2-en-4-yn-1-ol | 250358-85-1

• 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: (Z)-3-methylnon-2-en-4-yn-1-ol
• CAS: 250358-85-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: MGLJHHIRJOMZDV-NTMALXAHSA-N

物化性质

• 沸点：
  259.9±23.0 °C(Predicted)
• 密度：
  0.907±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-3-methylnon-2-en-4-yn-1-ol 在 吡啶 、 三溴化磷 作用下， 以 乙醚 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-benzyl(3-methylnon-2-en-4-ynyl)amine
  参考文献：
  名称：

  钯催化的（Z）-（2-en-4-ynyl）胺的环异构化：取代吡咯的新合成

  摘要：

  （Z）-（2-En-4-ynyl）amines 1带有一个内部三键，在催化量的PdCl 2和KCl的作用下，在25-100°C的无水N，N中经历平滑的环异构化反应，形成吡咯2 -二甲基乙酰胺。当三键为末端时，发生自发的未催化环化为相应的吡咯。

  DOI：

  10.1016/s0040-4039(00)02206-1
• 作为产物：
  描述：

  (Z)-3-甲基戊-2-烯-4-炔-1-醇 在 正丁基锂 、 对甲苯磺酸 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 48.75h， 生成 (Z)-3-methylnon-2-en-4-yn-1-ol
  参考文献：
  名称：

  Palladium-Catalyzed Alkoxycarbonylation of (Z)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates

  摘要：

  Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.

  DOI：

  10.1021/ol102989q

文献信息

• General and Regioselective Synthesis of Substituted Pyrroles by Metal-Catalyzed or Spontaneous Cycloisomerization of (<i>Z</i>)-(2-En-4-ynyl)amines
  作者：Bartolo Gabriele、Giuseppe Salerno、Alessia Fazio

  DOI：10.1021/jo034850j

  日期：2003.10.1

  A general and regioselective synthesis of substituted pyrroles 2 by cycloisomerization of readily available (Z)-(2-en-4-ynyl)amines 1 is reported. Spontaneous cycloisomerization leading to 2 occurred in the course of preparation of enynamines bearing a terminal triple bond or a triple bond substituted with a phenyl or a CH2OTHP group. When the triple bond was substituted with an alkyl or alkenyl group

  据报道，通过容易获得的（Z）-（2-en-4-炔基）胺1的环异构化，一般和区域选择性地合成取代的吡咯2。在制备带有末端三键或被苯基或CH 2 OTHP基团取代的三键的烯胺的过程中发生自发的环异构化反应，导致2。当三键被烷基或烯基取代时，烯胺是稳定的并且可以通过金属催化转化为相应的吡咯。发现CuCl2是用于在C-3处取代的底物进行环异构化的出色催化剂，而PdX2与KX（X = Cl，I）结合使用则是在C-3处未取代的烯胺反应的优良催化剂。
• Intramolecular Carboxyamidation of Alkyne‐Tethered <i>O</i>‐Acylhydroxamates through Formation of Fe(III)‐Nitrenoids
  作者：Siyuan Su、Yu Zhang、Peng Liu、Donald J. Wink、Daesung Lee

  DOI：10.1002/chem.202303428

  日期：2024.1.26

  induced spontaneous or 4-(dimethylamino)pyridine-catalyzed O→O or O→N acyl group migration can generate a wide variety of N,O-containing heterocycles. DFT study suggests the Fe-nitrenoid intermediate preferentially reacts in a radical manifold to mediates a stepwise C−N/C−O bond formation rather than a concerted [3+2] cycloaddition mechanism.

  Zip and shift : 炔烃束缚的O-酰基异羟肟酸酯的分子内羧酰胺化，然后是热诱导自发或4-(二甲氨基)吡啶催化的O→O或O→N酰基迁移，可以生成多种含N 、 O的杂环。 DFT 研究表明，Fe-氮烯类中间体优先在自由基流形中反应，介导逐步的 C−N/C−O 键形成，而不是协调一致的 [3+2] 环加成机制。
• A General and Facile Synthesis of Substituted Furans by Palladium-Catalyzed Cycloisomerization of (<i>Z</i>)-2-En-4-yn-1-ols
  作者：Bartolo Gabriele、Giuseppe Salerno、Egidio Lauria

  DOI：10.1021/jo990847h

  日期：1999.10.1

  A general and facile synthesis of furans, based on Pd(II)-catalyzed cycloisomerization of (Z)-2-en-4-yn-1-ols, is described. Cycloisomerization reactions are carried out at 25-100 degrees C in the presence of a very simple catalytic system, consisting of K2PdI4, under essentially neutral conditions. This new methodology is very versatile and can be applied to the synthesis of a variety of substituted furans, including particularly fragile, naturally occurring furans such as rosefuran. Efficient synthetic approaches for the regioselective synthesis of suitably substituted (Z)-2-en-4-yn-1-ols have been developed.
• A New Co₂(CO)₈-Mediated Tandem [5 + 1]/[2 + 2 + 1]-Cycloaddition Reaction:  A One-Pot Synthesis of Tricyclic δ-Lactones from <i>cis</i>-Epoxy Ene-ynes
  作者：Arjan Odedra、Chang-Jung Wu、Reniguntala J. Madhushaw、Su-Lein Wang、Rai-Shung Liu

  DOI：10.1021/ja0346633

  日期：2003.8.1

  In the presence of Co2(CO)8 and CO, cis-epoxyalkynes bearing a tether olefin undergo a tandem [5 + 1]/[2 + 2 + 1]-cycloaddition to give tricyclic delta-lactones efficiently in a one-pot operation. The reaction mechanism is proposed to involve a cobalt-coordinated cyclic allene species.
• An Efficient and General Synthesis of Furan-2-acetic Esters by Palladium-Catalyzed Oxidative Carbonylation of (<i>Z</i>)-2-En-4-yn-1-ols
  作者：Bartolo Gabriele、Giuseppe Salerno、Francesca De Pascali、Mirco Costa、Gian Paolo Chiusoli

  DOI：10.1021/jo990848+

  日期：1999.10.1

  A variety of (Z)-2-en-4-yn-1-ols have been carbonylated under oxidative conditions to give substituted furan-a-acetic esters in good yields. The cyclization-alkoxycarbonylation process occurs in alcoholic media at 50-70 degrees C and under 100 atm pressure of a 9:1 mixture of carbon monoxide and air in the presence of catalytic amounts of PdI2 in conjunction with KI. The proposed reaction pathway involves the in situ isomerization of the initially formed (E)-2-[(alkoxycarbonyl)methylene]-2,5-dihydrofuran species, which in some cases have been isolated and shown to be the intermediates.