N-(p-toluenesulfonyl)-3-amino-3-(4-methoxyphenyl)-1-phenylprop-1-yne

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(p-toluenesulfonyl)-3-amino-3-(4-methoxyphenyl)-1-phenylprop-1-yne
• 英文别名: N-[1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-yl]-4-methylbenzenesulfonamide；N-[1-(4-methoxyphenyl)-3-phenylprop-2-ynyl]-4-methylbenzenesulfonamide
• 化学式: C₂₃H₂₁NO₃S
• 分子量: 391.491
• InChiKey: QBVHBFKLNDUHLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-ol 、 对甲苯磺酰胺 在 bis(acetylacetonato)dioxidomolybdenum(VI) 、 ammonium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以68%的产率得到N-(p-toluenesulfonyl)-3-amino-3-(4-methoxyphenyl)-1-phenylprop-1-yne
  参考文献：
  名称：

  钼（VI）催化的氧，氮和碳亲核试剂直接取代炔丙醇

  摘要：

  开发了由MoO 2（acac）2 / NH 4 PF 6催化的各种氧，氮和碳亲核试剂高效直接取代炔丙醇。通过这种通用实用的方法，可以适度获得良好的功能炔。

  DOI：

  10.1016/j.tetlet.2009.12.128

文献信息

• Al(OTf)3: an efficient recyclable catalyst for direct nucleophilic substitution of the hydroxy group of propargylic alcohols with carbon- and heteroatom-centered nucleophiles to construct C–C, C–O, C–N and C–S bonds
  作者：Mukut Gohain、Charlene Marais、Barend C.B. Bezuidenhoudt

  DOI：10.1016/j.tetlet.2011.12.060

  日期：2012.2

  A general and highly efficient Al(OTf)3-catalyzed methodology has been developed for the direct nucleophilic substitution of the hydroxy group in propargylic alcohols with a variety of carbon- and heteroatom-centered nucleophiles such as alcohols, aromatic compounds, amides, and thiols, leading to the construction of C–C, C–O, C–N and C–S bonds.

  已经开发了一种通用且高效的Al（OTf）3催化方法，用于用各种以碳原子和杂原子为中心的亲核试剂（例如醇，芳族化合物，酰胺和硫醇）直接取代炔丙醇中的羟基，导致建立C–C，C–O，C–N和C–S键。
• Alkynyl Borrowing: Silver-Catalyzed Amination of Secondary Propargylic Alcohols via C(sp³)–C(sp) Bond Cleavage
  作者：Xin Zhuang、Min Zhu、Chuan-Ming Hong、Zhen Luo、Wan-Fang Li、Qing-Hua Li、Qun-Li Luo、Tang-Lin Liu

  DOI：10.1021/acs.joc.2c00297

  日期：2022.4.15

  The silver-catalyzed alkynyl borrowing amination of secondary propargyl alcohols via C(sp3)–C(sp) bond cleavage has been developed. This new strategy was based on the β-alkynyl elimination of propargyl alcohols and alkynyl as the borrowing subject. This alkynyl borrowing amination featured high atom economy, wide functional group tolerance, and high efficiency.

  已经开发了通过 C(sp 3 )-C(sp) 键断裂对仲炔丙醇进行银催化的炔基借位胺化。这种新策略基于炔丙醇的 β-炔基消除和炔基作为借用对象。这种炔基借用胺化具有原子经济性高、官能团耐受性宽、效率高等特点。
• Dimethylzinc-Mediated Alkynylation of Imines
  作者：Lorenzo Zani、Silvia Alesi、Pier Giorgio Cozzi、Carsten Bolm

  DOI：10.1021/jo052273o

  日期：2006.2.1

  [GRAPHICS]The treatment of various aromatic and aliphatic aldimines with a mixture of a terminal alkyne and a commercially available dimethylzinc solution in toluene yields the corresponding protected propargylic amines in moderate to excellent yields. The reaction proceeds in the absence of any activator. These observations led to the development of a three-component synthesis of propargylic amines in which the product was obtained upon mixing an aldehyde with ortho-methoxyaniline and phenylacetylene in the presence of dimethylzinc, through in situ formation of the corresponding imine.