3-methylnon-1-en-4-yn-3-ol | 103273-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methylnon-1-en-4-yn-3-ol
• 英文别名: 3-methyl-non-1-en-4-yn-3-ol；3-Methyl-non-1-en-4-in-3-ol
• CAS: 103273-23-0
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: QWJXRMOCPQGALF-UHFFFAOYSA-N

物化性质

• 沸点：
  61-61.5 °C(Press: 3.5 Torr)
• 密度：
  0.897±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3-methylnon-1-en-4-yn-3-ol 在 palladium(II) iodide 亚硫酸 、 potassium iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 3.0h， 生成 5-ethyl-3-methyl-2-pentylfuran
  参考文献：
  名称：

  A General and Facile Synthesis of Substituted Furans by Palladium-Catalyzed Cycloisomerization of (Z)-2-En-4-yn-1-ols

  摘要：

  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.

  DOI：

  10.1021/jo990847h
• 作为产物：
  描述：

  1-己炔 在 lithium amide 、 乙醚 、 氨 作用下， 生成 3-methylnon-1-en-4-yn-3-ol
  参考文献：
  名称：

  HYPNOTICS AND ANTICONVULSANTS. I. TERTIARY ACETYLENIC CARBINOLS

  摘要：

  DOI：

  10.1021/jo01369a014

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。
• Pd-Catalyzed Enantioselective (3+2)-Cycloaddition of Vinyl-Substituted Oxyallyl Carbonates with Isocyanates and Ketones
  作者：Xuemei Pan、Limei Yu、Simin Wang、Rui Wu、Chunyan Ou、Minghui Xu、Bin Chen、Yuanji Gao、Hai-Liang Ni、Ping Hu、Bi-Qin Wang、Peng Cao

  DOI：10.1021/acs.orglett.2c00290

  日期：2022.3.25

  C,O-dipole for enantioselective Pd-catalyzed (3+2) cycloaddition. The corresponding oxyallyl-Pd species was weakly nucleophilic to react with activated carbonyl compounds, affording multisubstituted and enantioenriched oxazolidinones and 1,3-dioxolanes with a high degree of chemo- and stereoselectivity. The synthetic transformations of oxazolidinone product were carried out to build enantioenriched

  乙烯基取代的碳酸氧烯丙酯被用作一种新的 C,O-偶极子，用于对映选择性 Pd 催化的 (3+2) 环加成反应。相应的 oxyallyl-Pd 物质具有弱亲核性，可与活性羰基化合物反应，从而提供具有高度化学和立体选择性的多取代和对映体富集的恶唑烷酮和 1,3-二氧戊环。对恶唑烷酮产物进行合成转化以构建对映体富集的α-手性氨基酮和环氧衍生物。
• Novel Synthesis of Substituted Thiophenes by Palladium-Catalyzed Cycloisomerization of (<i>Z</i>)-2-En-4-yne-1-thiols
  作者：Bartolo Gabriele、Giuseppe Salerno、Alessia Fazio

  DOI：10.1021/ol991297c

  日期：2000.2.1

  [reaction: see text] The first example of palladium-catalyzed cycloisomerization of (Z)-2-en-4-yne-1-thiols 1 to give substituted thiophenes 2 is reported. Cycloisomerization reactions are carried out under nitrogen at 25-100 degrees C in N,N-dimethylacetamide as the solvent in the presence of catalytic amounts of PdI2 in conjunction with KI to give the corresponding thiophenes in 43-94% yield.

  [反应：见正文]报告了钯催化的（Z）-2-en-4-yne-1-thiols 1的环异构化反应，得到取代的噻吩2的第一个例子。在催化量的PdI2和KI存在下，在氮气，25-100℃，N，N-二甲基乙酰胺为溶剂的条件下，进行环异构化反应，得到相应的噻吩，收率为43-94％。
• Versatile Synthesis of Pyrrole-2-acetic Esters and (Pyridine-2-one)-3-acetic Amides by Palladium-Catalyzed, Carbon Dioxide-Promoted Oxidative Carbonylation of (Z)-(2-En-4-ynyl)amines
  作者：Bartolo Gabriele、Giuseppe Salerno、Alessia Fazio、Lucia Veltri

  DOI：10.1002/adsc.200606085

  日期：2006.10

  The oxidative carbonylation of readily available (Z)-(2-en-4-ynyl)amines, catalyzed by the PdI2-KI system, selectively afforded in satisfactory yields (40–95 %) either pyrrole-2-acetic ester or (pyridine-2-one)-3-acetic amide derivatives, depending on the susbtitution pattern of the substrate and the reaction conditions. The presence of an excess of carbon dioxide proved in most cases to be beneficial

  由PdI 2 -KI体系催化的，易于获得的（Z）-（2-en-4-ynyl）胺的氧化羰基化选择性地提供了令人满意的产率（40-95％）的吡咯-2-乙酸酯或（吡啶-2-酮）-3-乙酰胺衍生物，取决于底物的取代方式和反应条件。在大多数情况下，过量二氧化碳的存在对反应速率和产物选择性都有利。
• 52. Studies in the polyene series. Part XVI. The condensation of αβ-unsaturated ketones with 1-hexyne
  作者：J. Cymerman、I. M. Heilbron、E. R. H. Jones

  DOI：10.1039/jr9440000144

  日期：——