N-(p-toluenesulfonyl)-3-amino-3-phenyl-1-(trimethylsilyl)prop-1-yne | 879208-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(p-toluenesulfonyl)-3-amino-3-phenyl-1-(trimethylsilyl)prop-1-yne
• 英文别名: 4-methyl-N-(1-phenyl-3-trimethylsilylprop-2-ynyl)benzenesulfonamide
• CAS: 879208-17-0
• 化学式: C₁₉H₂₃NO₂SSi
• 分子量: 357.549
• InChiKey: ZTLBBDNDGSBRRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(p-toluenesulfonyl)-3-amino-3-phenyl-1-(trimethylsilyl)prop-1-yne 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到4-methyl-N-(1-phenylprop-2-yn-1-yl)benzenesulfonamide
  参考文献：
  名称：

  Dimethylzinc-Mediated Alkynylation of Imines

  摘要：

  [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.

  DOI：

  10.1021/jo052273o
• 作为产物：
  描述：

  1-苯基-3-三甲基硅烷-2-丙炔-1-醇 、 对甲苯磺酰胺 在 silver tetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以30%的产率得到N-(p-toluenesulfonyl)-3-amino-3-phenyl-1-(trimethylsilyl)prop-1-yne
  参考文献：
  名称：

  炔基借用：通过 C(sp3)–C(sp) 键裂解银催化的仲炔丙醇胺化

  摘要：

  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。

  DOI：

  10.1021/acs.joc.2c00297

文献信息

• Regioselective synthesis of highly functionalized alkenylboronates by Cu-catalyzed borylation of propargylic silylalkynes
  作者：Yeong Eun Kim、DingXi Li、Jaesook Yun

  DOI：10.1039/c5dt00144g

  日期：——

  High regioselectivity was achieved in the Cu(I)-catalyzed borylation of internal propargylic alkynes with a silyl substituent to afford multifunctionalized alkenylboron compounds. While both the silyl and propargylic substituents are known to act as directing groups, a N-heterocyclic carbene (NHC)–Cu complex furnished β-vinylboronate products (relative to Si) with high selectivity.

  在内部炔丙基炔烃与甲硅烷基取代基的Cu（I）催化的硼化中获得了高区域选择性，从而提供了多官能化的烯基硼化合物。众所周知，甲硅烷基和炔丙基取代基都可以作为导向基团，而N-杂环卡宾（NHC）-Cu络合物可提供高选择性的β-乙烯基硼酸酯产品（相对于Si）。
• Gold(III)-Catalyzed Propargylic Substitution Reaction Followed by Cycloisomerization for Synthesis of Poly-Substituted Furans from N-Tosylpropargyl Amines with 1,3-Dicarbonyl Compounds
  作者：Nobuyoshi Morita、Shingo Uchida、Hitomi Chiaki、Naho Ishii、Kentaro Tanikawa、Kosaku Tanaka、Yoshimitsu Hashimoto、Osamu Tamura

  DOI：10.3390/molecules29020378

  日期：——

  The treatment of N-tosylpropargyl amines 1 with 1,3-dicarbonyl compounds 2 in the presence of AuBr3 (5 mol%) and AgOTf (15 mol%) afforded poly-substituted furans 3 in good-to-high yields via the gold-catalyzed cleavage of the sp3 carbon–nitrogen bond.

  在 AuBr3 （5 mol%） 和 AgOTf （15 mol%） 存在下，用 1,3-二羰基化合物 2 处理 N-甲苯磺酰丙炔氨胺 1，通过金催化裂解 sp3 碳-氮键，以良好到高的产率得到多取代呋喃 3。
• Redox-Neutral Synthesis of β-Amino Aldehydes from Imines by an Alkynylation/Hydration Sequence
  作者：Aurélie Labonne、Lorenzo Zani、Lukas Hintermann、Carsten Bolm

  DOI：10.1021/jo070745o

  日期：2007.7.1

  N-Protected beta-amino aldehydes have been prepared starting from imines through a sequence involving a Zn-mediated direct alkynylation followed by a Ru-catalyzed anti-Markovnikov alkyne hydration. The rate and the efficiency of the latter reaction are enhanced by the use of microwave irradiation. The possibility to carry out a one-pot Ru-catalyzed hydration/oxidation process from a terminal alkyne to a carboxylic acid was demonstrated, which provided direct access to a N-protected beta-amino acid from the corresponding terminal alkyne.