5-iodo-1-(4-methoxyphenyl)pent-1-yne | 154476-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-iodo-1-(4-methoxyphenyl)pent-1-yne
• 英文别名: 1-(5-iodo-1-pentyn-1-yl)-4-methoxybenzene；1-(5-iodopent-1-ynyl)-4-methoxybenzene
• CAS: 154476-91-2
• 化学式: C₁₂H₁₃IO
• 分子量: 300.139
• InChiKey: BJVHXAQLEFRUEO-UHFFFAOYSA-N

物化性质

• 沸点：
  340.6±27.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-iodo-1-(4-methoxyphenyl)pent-1-yne 在 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 13.33h， 生成
  参考文献：
  名称：

  Synthesis of 2-Azaspiro[4.6]undec-7-enes from N-Tosyl-N-(3-arylpropargyl)-Tethered 3-Methylcyclohex-2-en-1-ols

  摘要：

  The FeCl3-promoted synthesis of 2-azaspiro[4.6]-undec-7-ene rings proceeds via ring expansion/cyclization/chlorination of N-tosyl-N-(3-arylpropargyl)-tethered 6-methylbicyclo[4.1.0]heptan-2-ols. This azaspirocyclic ring skeleton can also be obtained in one pot from the tert-butyldimethylsilyl-protected N-tosyl-N-(3-arylpropargyl)-tethered 3-methylcyclohex-2-en-1-ols and diethylzinc/diiodomethane.

  DOI：

  10.1021/jo301764g
• 作为产物：
  描述：

  4-碘苯甲醚 在 Pd/Cu 碘 、 三苯基膦 作用下， 生成 5-iodo-1-(4-methoxyphenyl)pent-1-yne
  参考文献：
  名称：

  Synthesis of substituted (α-methylene lactams by rhodium catalysed carbonylation of acetylenic amines

  摘要：

  Reactions of gamma- and beta-aminoalkynes, (2) and (5) with hydrogen and carbon monoxide in the presence of rhodium catalysts give substituted alpha-methylene-2-piperidinones (7) and 2-pyrrolidinones (11).

  DOI：

  10.1016/s0040-4020(01)86969-6

文献信息

• Alkylation of Terminal Alkynes under Zinc Lewis Acid Catalysis and Its Mechanistic Studies
  作者：Mana Osano、Takeru Kida、Kyohei Yonekura、Teruhisa Tsuchimoto

  DOI：10.1002/adsc.201801685

  日期：2019.6.18

  and proton sponge in toluene, terminal alkynes were found to undergo the alkylation by alkyl triflates to provide unsymmetrical internal alkynes. This is the first example that a simple alkyl chain other than benzylic and norbornyl units can be introduced onto the alkynyl carbon atom under Lewis acid catalysis. Mechanistic studies revealed that the activation of the alkyne by the zinc Lewis acid and proton

  用锌路易斯酸催化剂和质子海绵在甲苯中，发现末端炔烃通过烷基三氟甲磺酸酯进行烷基化以提供不对称的内部炔烃。这是第一个实例，可以在路易斯酸催化下将除苄基和降冰片基单元以外的简单烷基链引入炔基碳原子上。机理研究表明，路易斯酸锌和质子海绵对炔烃的活化是引发生成单炔基锌物质的反应的触发点，后者与三氟甲磺酸烷基酯反应生成内部炔烃。在这个系统中，根本的途径是不可能的。
• Enamides and Enesulfonamides as Nucleophiles: Formation of Complex Ring Systems through a Platinum(II)-Catalyzed Addition/Friedel−Crafts Pathway
  作者：Jennifer A. Kozak、Jennifer M. Dodd、Tyler J. Harrison、Katherine J. Jardine、Brian O. Patrick、Gregory R. Dake

  DOI：10.1021/jo901512m

  日期：2009.9.18

  (enesulfonamides and enamides) tethered to an 1-arylalkynyl fragment undergo a platinum(II)-catalyzed tandem alkyne addition/Friedel−Crafts ring closure to form nitrogen-containing polycyclic structures. Regioselectivity in the initial addition of the enesulfonamide or enamide nucleophile to the platinum(II)−alkyne complex is important. Electron-rich arenes and heterocycles led to the formation of products

  拴系到1-芳基炔基片段的环状烯胺衍生物（烯磺酰胺和酰胺）经过铂（II）催化的串联炔烃加成/弗里德勒-克拉夫茨环闭合形成含氮多环结构。在将烯磺酰胺或烯酰胺亲核试剂最初添加到铂（II）-炔烃络合物中时，区域选择性很重要。富电子的芳烃和杂环导致了最初的6-内环化反应形成的产物。给出了此过程的23个示例。
• Diastereoselective Synthesis of 2-Arylmethylene-6-hydroxyspiro[4.5]deca-7-ones via FeCl₃·6H₂O-Catalyzed Spiroannulation/Hydride Transfer of 6-(5-Arylpent-4-yn-1-yl)-7-oxabicyclo[4.1.0]heptan-2-ols
  作者：Hsin-Hui Lin、Kuan-Yi Lee、Yin-An Chen、Chi-Fan Liu、Ming-Chang P. Yeh

  DOI：10.1021/jo5023266

  日期：2014.12.5

  In the presence of a catalytic amount of FeCl3 center dot 6H(2)O, 6-(5-arylpent-4-yn-1-yl)-7-oxabicyclo[4.1.0]heptan-2-ols underwent attack of the pendant acetylene at the iron-activated oxirane to give a vinylic carbocation. Hydride transfer from the carbinol carbon to the newly formed cation center furnished 2-arylmethylene-6-hydroxyspiro[4.5]deca-7-ones in excellent stereoselectivity and good yields.
• Campi Eva M., Chong J. Michael, Jackson W. Roy, Van Der Schoot Marcel, Tetrahedron, 50 (1994) N 8, S 2533-2542
  作者：Campi Eva M., Chong J. Michael, Jackson W. Roy, Van Der Schoot Marcel

  DOI：——

  日期：——