1-(but-2-ynyl)naphthalene | 138102-19-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(but-2-ynyl)naphthalene
• 英文别名: 1-But-2-ynylnaphthalene
• CAS: 138102-19-9
• 化学式: C₁₄H₁₂
• 分子量: 180.249
• InChiKey: KGLROCNVKCPVMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(but-2-ynyl)naphthalene 、 频那醇硼烷 在 C₄₁H₃₆Cl₂CoP₂ 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 生成 (Z)-4,4,5,5-tetramethyl-2-(1-(naphthalen-1-yl)but-2-en-2-yl)-1,3,2-dioxaborolane 、 C₂₀H₂₅BO₂
  参考文献：
  名称：

  高区域选择性钴催化内炔烃的硼氢化

  摘要：

  利用新开发的环丙烷基二膦配体修饰的钴催化剂，实现了不对称内炔烃的高选择性硼氢化反应，该反应具有独特的区域选择性、广泛的底物范围和良好的官能团相容性。目前的协议能够合成新的烯基硼酸盐，并提高了生物活性化合物的合成效率。

  DOI：

  10.1002/anie.202208473
• 作为产物：
  描述：

  naphthalen-1-ylmethyl but-2-ynoate 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以88%的产率得到1-(but-2-ynyl)naphthalene
  参考文献：
  名称：

  Decarboxylative Benzylations of Alkynes and Ketones

  摘要：

  Benzyl esters of propiolic and beta-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.

  DOI：

  10.1021/ja1035557

文献信息

• A new practical method for the synthesis of acetylenes.
  作者：Jean Boivin、Laurent Elkaim、Paul G. Ferro、Samir Z. Zard

  DOI：10.1016/s0040-4039(00)92375-x

  日期：1991.9

  The reaction of isaxazol-5-ones derived from β-keto esters and hydroxylamine with sodium nitrite and ferrous sulphate in aqueous acetic acid affords the corresponding acetylenes in moderate to good yield.

  衍生自β-酮酸酯和羟胺的异恶唑-5-酮与亚硝酸钠和硫酸亚铁在乙酸水溶液中的反应以中等至良好的产率提供了相应的乙炔。
• Decarboxylative Benzylations of Alkynes and Ketones
  作者：Robert R. P. Torregrosa、Yamuna Ariyarathna、Kalicharan Chattopadhyay、Jon A. Tunge

  DOI：10.1021/ja1035557

  日期：2010.7.14

  Benzyl esters of propiolic and beta-keto acids undergo catalytic decarboxylative coupling when treated with appropriate palladium catalysts. Such decarboxylative couplings allow the benzylation of alkynes without the use of strong bases and/or organometallics. This allows the synthesis of sensitive benzylic alkynes that are prone to undergo isomerizations under basic conditions. Additionally, decarboxylation facilitates the site-specific benzylation of diketones and ketoesters under mild, base-free conditions. Ultimately, the methodology described expands our ability to cross-couple medicinally relevant heterocycles.
• Highly Regioselective Cobalt‐Catalyzed Hydroboration of Internal Alkynes
  作者：Yan‐Dong Zhang、Xiao‐Yu Li、Qian‐Kun Mo、Wen‐Bin Shi、Jia‐Bao Zhao、Shou‐Fei Zhu

  DOI：10.1002/anie.202208473

  日期：2022.9.5

  A highly selective hydroboration of unsymmetrical internal alkynes featuring unique regioselectivity, broad substrate scope and good functional group compatibility was realized by using cobalt catalysts modified with newly developed cyclopropane-based diphosphine ligands. The current protocol enabled the synthesis of novel alkenyl borates and improved the synthetic efficiency of bioactive compounds

  利用新开发的环丙烷基二膦配体修饰的钴催化剂，实现了不对称内炔烃的高选择性硼氢化反应，该反应具有独特的区域选择性、广泛的底物范围和良好的官能团相容性。目前的协议能够合成新的烯基硼酸盐，并提高了生物活性化合物的合成效率。