N-benzyl-5-phenylpent-4-yn-1-amine | 175347-87-2

• 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-5-phenylpent-4-yn-1-amine
• CAS: 175347-87-2
• 化学式: C₁₈H₁₉N
• 分子量: 249.356
• InChiKey: PERAGQUFVOSXGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-5-phenylpent-4-yn-1-amine 在 三甲基氯硅烷 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 (3Z)-1-benzyl-3-[chloro(phenyl)methylidene]piperidine
  参考文献：
  名称：

  Aprotic Chloride and Bromide-promoted Alkyne-Iminium Ion Cyclizations

  摘要：

  DOI：

  10.3987/com-95-s96
• 作为产物：
  描述：

  5-苯基-4-戊炔-1-醇 在 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.5h， 生成 N-benzyl-5-phenylpent-4-yn-1-amine
  参考文献：
  名称：

  钴 (II) 基金属自由基催化对炔丙基 C(sp3)?H 键的化学选择性胺化

  摘要：

  已经通过钴 (II) 基金属基催化对 N-双同炔氨磺酰基叠氮化物证明了炔丙 C(sp 3 )  H 键的高度化学选择性分子内胺化。在 D 2h对称酰胺卟啉配体 3,5-Di t Bu-IbuPhyrin 的支持下，钴 (II) 催化的 C  H 胺化在中性和非氧化条件下有效进行，无需任何添加剂，并生成 N 2作为唯一的副产品。金属自由基胺化适用于二级和三级炔丙C H 底物具有异常高的官能团耐受性，从而为功能化炔丙胺衍生物的高产合成提供了一种直接方法。

  DOI：

  10.1002/anie.201400557

文献信息

• Highly Efficient and Regioselective Platinum(II)-Catalyzed Tandem Synthesis of Multiply Substituted Indolines and Tetrahydroquinolines
  作者：Xin-Yuan Liu、Chi-Ming Che

  DOI：10.1002/anie.200805383

  日期：2009.3.16

  special advantage: The platinum(II)‐catalyzed tandem cyclization of aminoalkynes with 1,3‐diketones offers a new and highly efficient method for the synthesis of indolines and tetrahydroquinolines (see scheme; M.S.=molecular sieves). This transformation affords good to excellent product yields with high regio‐ and chemoselectivity under mild reaction conditions.

  一个特殊的优势：带有1,3-二酮的铂（Ⅱ）催化的氨基炔的串联环化为合成二氢吲哚和四氢喹啉提供了一种高效的新方法（见方案； MS =分子筛）。在温和的反应条件下，这种转化可提供良好的产品收率，具有很高的区域选择性和化学选择性。
• Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition
  作者：Aireal D. Jenkins、Ananda Herath、Minsoo Song、John Montgomery

  DOI：10.1021/ja206722t

  日期：2011.9.14

  Strategies for the reductive cycloaddition of enals or enoates with alkynes have been developed. The enal-alkyne cycloaddition directly affords cyclopentenols, whereas the enoate-alkyne cycloaddition affords the analogous cyclopentenones. The mechanism of these processes likely involves formation and protonation of a metallacyclic intermediate. The general strategy provides a straightforward entry

  已经开发了烯醛或烯酸酯与炔烃的还原环加成的策略。烯醛-炔环加成直接提供环戊烯醇，而烯酸酯-炔环加成提供类似的环戊烯酮。这些过程的机制可能涉及金属环中间体的形成和质子化。一般策略提供了从简单、稳定的 π 系统到五元环产品的直接入口。
• Evolution of Efficient Strategies for Enone−Alkyne and Enal−Alkyne Reductive Couplings
  作者：Wei Li、Ananda Herath、John Montgomery

  DOI：10.1021/ja9083607

  日期：2009.11.25

  Strategies for the reductive coupling of enones or enals with alkynes have been developed. The reducing agents employed include organozincs, organoboranes, organosilanes, and methanol. The latter of these strategies is simple, cost-effective, and tolerant of many functional groups. Isotopic labeling strategies have provided supporting evidence for the mechanistic proposals.
• Highly Chemoselective and Stereoselective Synthesis of <i>Z</i>-Enol Silanes
  作者：Ananda Herath、John Montgomery

  DOI：10.1021/ja802844v

  日期：2008.7.1

  Three-component nickel-catalyzed couplings of enals, alkynes, and silanes have been developed as a new entry to enol silanes. The enol silane and a trisubstituted alkene are both formed with > 98:2 stereoselectively, and the reaction tolerates a broad range of functionality including aldehydes, ketones, esters, free hydroxyls, and basic secondary amines. A mechanistic pathway involving the formation of a metallacycle that possesses and eta(1) nickel O-enolate motif explains the high level of stereoselection.
• Highly Selective Construction of Medium-Sized Lactams by Palladium-Catalyzed Intramolecular Hydroaminocarbonylation of Aminoalkynes
  作者：Yue Hu、Hanmin Huang

  DOI：10.1021/acs.orglett.7b02284

  日期：2017.10.6

  A novel palladium-catalyzed intramolecular hydro-aminocarbonylation of aminoalkynes has been developed. This direct and operationally simple protocol provides a rapid and reliable approach to a diverse array of valuable seven- and eight-membered lactams with high chemoselectivity and regioselectivity. The high selectivity might be attributed to rational tuning the electronic nature of the amine moiety and the palladium catalyst, which enabled this transformation to proceed in the absence of acidic or any other additives under fairly mild reaction conditions. This method paves the way for the synthesis of medium-sized lactams.