3-丁炔-1-氧化钠 | 42474-56-6

• 分子结构分类: 有机化合物 - 乙炔化物
• 中文名称: 3-丁炔-1-氧化钠
• 英文名称: sodium 3-butyn-1-oxide
• 英文别名: sodium salt of 4-hydroxy-1-butyne；sodium;but-3-yn-1-olate
• CAS: 42474-56-6
• 化学式: C₄H₅O*Na
• 分子量: 92.0729
• InChiKey: WFXNIUGMCBYSAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.63
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.06
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3-(methylsulfonyl)-5-phenyl-1,2,4-triazine 、 3-丁炔-1-氧化钠 以 四氢呋喃 为溶剂， 以67%的产率得到3-(3-丁炔氧基)-5-苯基-1,2,4-三嗪
  参考文献：
  名称：

  1,2,4-三嗪的进一步分子内反应。呋喃并[2,3- ]吡啶和二氢吡喃并[2,3- ]吡啶的合成

  摘要：

  3-（3-丁炔氧基）-和3-（4-戊氧基）-1,2,4-三嗪容易发生分子内Diels-Alder反应，生成2,3-二氢呋喃（2,3- ）吡啶和二氢吡喃（2， 3- ）吡啶。前者很容易用DDQ脱氢为呋喃（2,3- ）吡啶。

  DOI：

  10.1016/s0040-4039(00)85497-0

文献信息

• Palladium Catalysed Tandem Cyclisation–Anion Capture. Part 5: Cascade Hydrostannylation-bis-cyclisation-intramolecular Anion Capture. Synthesis of Bridged- and Spiro-Cyclic Small and Macrocyclic Heterocycles
  作者：Adele Casaschi、Ronald Grigg、José M Sansano、David Wilson、James Redpath

  DOI：10.1016/s0040-4020(00)00660-8

  日期：2000.9

  A series of O- and N-α,ω-enyne derivatives of 2-iodoarylethers and 2-iodoarylamides undergo palladium catalysed cascade hydrostannylation of the ω-alkyne moiety at 0–25°C followed by bis-cyclisation at 100–110°C terminating in intramolecular sp3–sp2 Stille coupling. These cascades provide a wide range of 5/6 and 5/12–17 membered bicyclic spiro- and bridged-ring heterocycles.

  一系列2-碘代芳基醚和2-碘代芳基酰胺的O-和N -α，ω-烯炔衍生物在0–25°C下经历钯催化的ω-炔烃部分的级联氢化锡烷基化反应，然后在100–110°C下进行双环化终止于分子内sp 3 –sp 2斯蒂勒偶联。这些级联提供了广泛的5/6和5 / 12–17元双环螺环和桥环杂环。
• Attempts at vinyl radical carbonylation through cyclization onto carbonyl and cyano groups
  作者：Pier Carlo Montevecchi、Maria Luisa Navacchia、Piero Spagnolo

  DOI：10.1016/s0040-4020(98)00458-x

  日期：1998.7

  Sulfanylvinyl radicals 4–6, 16, produced from toluenesulfanyl radical addition to alkynes 1–3, 15, gave only products arising from cyclization onto the thiophenyl ring and H-abstraction. No products were obtained deriving from possible 5-membered cyclization onto the esteric or thioesteric carbonyl group. Similar results were obtained from toluenesulfanyl radical addition to alkynyl nitriles 20 and

  Sulfanylvinyl基团4-6，16，从toluenesulfanyl基加至炔烃制备1-3，15，给从环化而产生到噻吩环和H-抽象仅产品。没有得到从可能的五元环化到酯或硫代酯羰基上的产物。从甲苯硫烷基到炔基腈20和24的加成反应也得到了相似的结果，但没有提供任何证据表明5或6元乙烯基自由基环合到脂肪族氰基上。相反，甲苯硫基-和苯硫基-乙烯基基团32和37a均平滑地环化到芳族氰基上，从而生成酮35和39。该协议代表了一种新型的间接自由基羰基化，并提供了一种有用的合成茚满的方法。
• Organocuivreux vinyliques
  作者：A. Alexakis、J. Normant、J. Villieras

  DOI：10.1016/s0022-328x(00)91950-8

  日期：1975.9

  The syn addition of alkylcopper compounds to various alkynes HCC(CH2)2Z (n = 2, 3, Z = X, NEt2, SEt, OR) shows a regio-selectivity dependant on various factors, the major factors being the nature of the function and the solvent. The vinylcopper derivatives thus obtained have been carboxylated, iodinated and alkylated.

  烷基铜化合物向各种炔烃HCC（CH 2）2 Z（n = 2，3，Z = X，NEt 2，SEt，OR）的顺式加成显示区域选择性取决于各种因素，主要因素是功能的性质和溶剂。由此获得的乙烯基铜衍生物已被羧化，碘化和烷基化。
• Intramolekulare diels-alder-reaktionen mit substituierten 1,2,4,5-tetrazinen und 1,2,4-triazinen
  作者：Gunther Seitz、Lucia Görge、Sabine Dietrich

  DOI：10.1016/s0040-4039(00)98733-1

  日期：1985.1

  1,2,4,5-tetrazines as well as 1,2,4-triazines carrying sidechain dienophiles react in an intramolecular Diels-Alder cycloaddition with inverse electron demand to yield novel bicyclic pyridazines and pyridines.

  带有侧链亲二烯体的1,2,4,5-四嗪以及1,2,4-三嗪在分子内Diels-Alder环加成反应中产生反电子需求，从而生成新型双环哒嗪和吡啶。
• Stereoselective Cyclizations and Rearrangements in Vinyl Radicals Promoted by Regioselective Sulfanyl Radical Addition to Enynes
  作者：Pier Carlo Montevecchi、Maria Luisa Navacchia

  DOI：10.1021/jo9701142

  日期：1997.8.1

  Regioselective radical addition of 4-cyanotoluenethiol (1a) to enynes 3-6 leads to vinyl radicals 7-10 that can undergo five- or six-membered cyclization onto styrene or terminal double bonds in competition with 5-exo cyclization onto the aryl ring, The latter affords spiro-cyclohexadienyl radical intermediates which can either be trapped by 2-cyanoisopropyl radicals or give 1,4-aryl migration products. Regioselective radical addition of phenethanethiol (1b) to enynes 3-6 gives radicals 11-14 which undergo five- or six-membered cyclization onto the alkene double bond; the stereoelectronically disfavored 6-exo cyclization can compete with intermolecular hydrogen abstraction and (to a small extent) with 1,5-hydrogen migration. The 5- and 6-(pi-exo)exo cyclization of vinyl radicals 7, 9, 11-13 is highly stereoselective and exclusively or predominately affords products deriving from the (Z)-isomers. Stereochemical evidence indicates that the six-membered endo-cyclization products 30 and 50 could derive from a direct 6-endo cyclization of (E)-radicals (E)-10 and (E)-14 rather than from a 5-exo cyclization/ring expansion process. Sulfanyl radical addition to enynes 3-5 is highly regioselective to the terminal triple bond. In contrast, reaction elf thiols 1a,b with enyne 6 leads to products deriving from sulfanyl radical addition to both the CC triple and double bond. This behavior is accounted for by assuming that sulfanyl radical addition to the alkyne triple bond is not reversible, while the addition to the alkene double bond is. Vinyl radical 10 affords product 33 by a rare 1,4-hydrogen migration/fragmentation process.