N-benzyl-3-phenyl-N-(3-phenylprop-2-yn-1-yl)prop-2-yn-1-amine | 345983-67-7

• 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-benzyl-3-phenyl-N-(3-phenylprop-2-yn-1-yl)prop-2-yn-1-amine
• 英文别名: N-benzyl-3-phenyl-N-(3-phenylprop-2-ynyl)prop-2-yn-1-amine
• CAS: 345983-67-7
• 化学式: C₂₅H₂₁N
• 分子量: 335.448
• InChiKey: RTXCAPLIDZCHCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Methylallylmagnesium Chloride 、 N-benzyl-3-phenyl-N-(3-phenylprop-2-yn-1-yl)prop-2-yn-1-amine 在 chromium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 4.33h， 以83%的产率得到8-aza-8-benzyl-3,3-dimethyl-2,5-diphenylbicyclo[4.3.0]nona-1,5-diene
  参考文献：
  名称：

  在CrCl3催化下，由甲基烯丙基铬酸酯或甲基烯丙基氯化镁介导的1,6-二炔的新型[2 + 2 + 2]环化。

  摘要：

  DOI：

  10.1021/ja015746r
• 作为产物：
  描述：

  聚合甲醛 、 苯基乙炔基三甲基硅烷 、 苄胺 在 copper(II) bis(trifluoromethanesulfonate) 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以80%的产率得到N-benzyl-3-phenyl-N-(3-phenylprop-2-yn-1-yl)prop-2-yn-1-amine
  参考文献：
  名称：

  Facile and Selective Synthesis of Propargylic Amines and 1,6-Diynes: One-Pot Three-Component Coupling Reactions of Alkynylsilanes, Aldehydes and Amines by a Cooperative Catalytic System Comprised of CuCl and Cu(OTf)₂

  摘要：

  Described herein is a three-component coupling reaction of alkynylsilanes, aldehydes and amines by a cooperative catalytic system comprised of CuCl and Cu(OTf)(2), leading to the production of a variety of propargyl amine derivatives. This catalytic system was successfully applied to the practical preparation of 1,6-diyne derivatives via twice-performed, domino-type coupling reactions.

  DOI：

  10.1055/s-2008-1077790

文献信息

• Site-Selective Labeling of Native Proteins by a Multicomponent Approach
  作者：Maheshwerreddy Chilamari、Landa Purushottam、Vishal Rai

  DOI：10.1002/chem.201605938

  日期：2017.3.17

  functionalization of proteins is an indispensable tool. Yet, selective labeling of native proteins has been an arduous task. The limited success of chemical methods allows N‐terminus protein labeling, but the examples with side‐chain residues are rare. Herein, we surpass this challenge through a multicomponent transformation that operates under physiological conditions in the presence of a protein, aldehyde, acetylene

  蛋白质的化学功能化是必不可少的工具。然而，天然蛋白质的选择性标记是一项艰巨的任务。化学方法取得的成功有限，可以进行N末端蛋白质标记，但是带有侧链残基的例子很少。在这里，我们通过在蛋白质，醛，乙炔和铜配体复合物存在下在生理条件下运行的多组分转化克服了这一挑战。该方法导致标记了九种不同蛋白质中的一个赖氨酸残基。
• Mild and Catalyst-Free Petasis/Decarboxylative Domino Reaction: Chemoselective Synthesis of <i>N</i>-Benzyl Propargylamines
  作者：Huangdi Feng、Huihui Jia、Zhihua Sun

  DOI：10.1021/jo502349a

  日期：2014.12.5

  domino reactions are attractive for assembling functionalized compounds. To this end, a one-pot catalyst-free chemoselective synthesis of N-benzyl propargylamines is reported with good functional group compatibility. This mild process involves in situ formation of an active amine through Petasis reaction of primary amines, formaldehyde solution, and boronic acids, which reacts with propiolic acids to give

  多组分多米诺反应对于组装功能化化合物具有吸引力。为此，报道了具有良好官能团相容性的N-苄基炔丙基胺的一锅无催化剂的化学选择性合成。这种温和的过程涉及通过伯胺，甲醛溶液和硼酸的Petasis反应在原位形成活性胺，后者与丙酸反应，通过脱羧偶联反应以高达94％的收率得到产物。
• PROCESS FOR PRODUCTION OF SUBSTITUTED BENZENE
  申请人：Okamoto Sentaro

  公开号：US20100168441A1

  公开（公告）日：2010-07-01

  Disclosed is a process for production of a substituted benzene, which comprises intramolecularly and/or intermolecularly trimerizing a triple bond in an alkyne in the presence of a transition metal catalyst to yield a substituted benzene compound. In the process, the transition metal catalyst is prepared from an iminomethylpyridine represented by the formula (1) or (2), a transition metal salt or a hydrate thereof, and a reducing agent in a reaction system and is used to perform the trimerization. The process can be used in any one of the intramolecular cyclization of a triyne compound, the cyclization of a diyne compound or an alkyne compound and the intermolecular cyclization of three molecules of an alkyne compound, is excellent in economic effectiveness and operability, and is practically advantageous. wherein R 1 and R 3 independently represent a linear or cyclic C 1 -C 20 aliphatic hydrocarbon group or the like; R 2 represents a hydrogen atom or the like; X represents a hydrogen atom, O or the like; and Y represents O, S or the like.

  揭示了一种生产取代苯的过程，包括在过渡金属催化剂存在下，使炔烃中的三键进行分子内和/或分子间三聚化，从而产生取代苯化合物。在该过程中，过渡金属催化剂由式（1）或（2）表示的亚甲基吡啶胺、过渡金属盐或其水合物以及还原剂在反应系统中制备，并用于进行三聚化反应。该过程可用于三炔化合物的分子内环化、双炔化合物或炔烃的环化，以及三分子炔烃的分子间环化，具有经济效益和操作性优越，并在实际中具有优势。其中，R1和R3独立表示线性或环状的C1-C20脂肪烃基或类似物；R2表示氢原子或类似物；X表示氢原子、氧或类似物；Y表示氧、硫或类似物。
• Synthesis of cyclopentadienones catalyzed by methylidynetricobalt nonacarbonyl
  作者：Takumichi Sugihara、Akihito Wakabayashi、Hiroko Takao、Hiroshi Imagawa、Mugio Nishizawa

  DOI：10.1039/b107985a

  日期：2001.11.22

  Easily prepared and air-stable methylidynetricobalt nonacarbonyl could be used as a catalyst for the intramolecular [2 + 2 + 1]-cocyclization of diynes and carbon monoxide producing cyclopentadienones.

  容易制备且空气稳定的亚甲基炔丙基九碳烯可以用作二炔与一氧化碳的环戊二烯酮分子内[2 + 2 + 1]-共环化的催化剂。
• Facile and Selective Synthesis of Propargylic Amines and 1,6-Diynes: One-Pot Three-Component Coupling Reactions of Alkynylsilanes, Aldehydes and Amines by a Cooperative Catalytic System Comprised of CuCl and Cu(OTf)₂
  作者：Norio Sakai、Naoki Uchida、Takeo Konakahara

  DOI：10.1055/s-2008-1077790

  日期：2008.6

  Described herein is a three-component coupling reaction of alkynylsilanes, aldehydes and amines by a cooperative catalytic system comprised of CuCl and Cu(OTf)(2), leading to the production of a variety of propargyl amine derivatives. This catalytic system was successfully applied to the practical preparation of 1,6-diyne derivatives via twice-performed, domino-type coupling reactions.