N-(naphthalen-1-ylmethyl)prop-2-en-1-amine | 134275-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(naphthalen-1-ylmethyl)prop-2-en-1-amine
• CAS: 134275-02-8
• 化学式: C₁₄H₁₅N
• mdl: MFCD06408397
• 分子量: 197.28
• InChiKey: FZYKMXDMHIZDEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 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-(naphthalen-1-ylmethyl)prop-2-en-1-amine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium aluminium tetrahydride 、 sodium acetate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 苯甲腈 为溶剂， 反应 4.0h， 生成 萘替芬
  参考文献：
  名称：

  Substrate-Directable Heck Reactions with Arenediazonium Salts. The Regio- and Stereoselective Arylation of Allylamine Derivatives and Applications in the Synthesis of Naftifine and Abamines

  摘要：

  The palladium-catalyzed, substrate-directable Heck-Matsuda reaction of allylamine derivatives with arenediazonium salts is reported. The reaction proceeds under mild conditions, with excellent regio- and stereochemical control as a function of coordinating groups present in the allylamine substrate. The distance between the olefin moiety and the carbonylic system seems to play a key role regarding the regiocontrol. The method presents itself as robust, as simple to carry out, and with wide synthetic scope concerning the allylic substrates and the type of arenediazonium employed. The synthetic potential of the method is illustrated by the short total syntheses of the bioactive compounds naftifine, abamine, and abamine SG.

  DOI：

  10.1021/jo201105z
• 作为产物：
  描述：

  Allyl-[1-naphthalen-1-yl-meth-(Z)-ylidene]-amine 在 C₂₁H₃₉NPPd^(1-)*C₂F₃O₂^(1-) 、 苯硅烷 、 水 作用下， 以 氘代氯仿 为溶剂， 反应 6.0h， 以87%的产率得到N-(naphthalen-1-ylmethyl)prop-2-en-1-amine
  参考文献：
  名称：

  Selective hydrosilylation of N-allylimines using a (3-iminophosphine)palladium precatalyst

  摘要：

  利用（3-亚磷腙基）钯催化剂进行氢硅烷基化反应，可以选择性地还原烯丙基亚胺中的亚胺基团。

  DOI：

  10.1039/c5cy01859e

文献信息

• Dearomative Intramolecular (4+3) Cycloadditions of Arenes with Epoxy and Aziridinyl Enolsilanes
  作者：Jesse Ling、Sarah Lam、Kam-Hung Low、Pauline Chiu

  DOI：10.1002/anie.201704155

  日期：2017.7.17

  enolsilanes with benzene, naphthalene, and anthracene derivatives is reported. Highly functionalized polycyclic alcohols and amines are generated under relatively mild reaction conditions with yields up to 89 %. Optically enriched cycloadducts are obtained from cycloadditions of enantiomerically pure epoxides and aziridines.

  报道了环氧和叠氮基烯醇硅烷与苯，萘和蒽衍生物的分子内（4 + 3）环加成。在相对温和的反应条件下可以生成高度官能化的多环醇和胺，收率高达89％。光学富集的环加合物是从对映体纯的环氧化物和氮丙啶的环加成反应中获得的。
• One-Pot Synthesis of Cyclopropane-Fused Cyclic Amidines: An Oxidative Carbanion Cyclization
  作者：Kirana Devarahosahalli Veeranna、Kanak Kanti Das、Sundarababu Baskaran

  DOI：10.1002/anie.201708138

  日期：2017.12.18

  No stopping! An efficient one-pot multistep process enabled the synthesis of novel cyclopropane-fused cyclic amidines with a quaternary center in good yields (see scheme). This method provides ready access to the 3-azabicyclo[n.1.0]alkane framework. The synthetic utility of the CuBr2-mediated oxidative cyclization was demonstrated by a short (four-step) synthesis of the antidepressant drug candidate

  不停！一种高效的一锅多步法能够合成具有四元中心的新型环丙烷稠合的环状am，收率很高（参见方案）。该方法提供了对3-氮杂双环[ n .1.0]烷烃框架的便捷访问。通过抗抑郁药候选药物GSK1360707的短时间（四步）合成，证明了CuBr 2介导的氧化环化的合成效用。
• RADIOACTIVE FLUORINE LABELING PRECURSOR COMPOUND AND METHOD FOR MANUFACTURING RADIOACTIVE FLUORINE LABELED COMPOUND USING THE SAME
  申请人：NIHON MEDI-PHYSICS CO., LTD.

  公开号：US20170066748A1

  公开（公告）日：2017-03-09

  There is provided a labeling precursor compound represented by the following general formula (2): wherein R 1 represents an alkynyl group, an alkynyloxy group, an azide group, an azidoalkyl group, an arylazide group, a monocyclic or condensed polycyclic aryl group or a nitrogen-containing heterocycle; R 2 and R 3 each independently represent an alkyl group or a hydroxyalkyl group which hydroxy group may be protected with a protecting group, and n is an integer of 1 or 2; R 6 represents an alkyl group or —CONR 11 R 12 wherein R 11 and R 12 each independently represent an alkyl group or a monocyclic or condensed polycyclic aryl group; and R 4 , R 5 , R 7 and R 8 each independently represent a hydrogen atom, an alkyl group or an alkoxy group.

  提供了一个标签前体化合物，表示为以下一般式（2）： 其中R1代表炔基，炔氧基，叠氮基，叠氮烷基，芳基叠氮基，单环或缩合多环芳基或含氮杂环；R2和R3分别独立地代表烷基或羟基烷基，其中羟基可能被保护基保护，n为1或2的整数；R6代表烷基或—CONR11R12，其中R11和R12分别独立地代表烷基或单环或缩合多环芳基；而R4、R5、R7和R8分别独立地代表氢原子、烷基或烷氧基。
• Synthesis of Thioalkyne-Substituted Thiazolidine-2-thiones Using Tris(tri­methylsilyl)methyllithium and Carbon Disulfide
  作者：Kazem Safa、Maryam Alyari

  DOI：10.1055/s-0034-1379253

  日期：——

  simple one-pot approach to the synthesis of 5-(iodomethyl)thiazolidine-2-thiones via multicomponent reaction of allylamines, carbon disulfide, and iodine under solvent-free conditions is presented. The obtained 5-(iodomethyl)thiazolidine-2-thiones were converted into silyl-protected­ terminal [(ethynylthio)methyl]-substituted thiazolidine-2-thiones by treatment with lithium 2,2,2-tris(trimethylsilyl)ethanedithioate

  摘要 提出了一种在无溶剂条件下通过烯丙胺，二硫化碳和碘的多组分反应合成5-（碘甲基）噻唑烷-2-硫酮的有效，环保，简单的一锅法。通过用2,2,2-三（三甲基甲硅烷基）乙二硫酸锂处理，将得到的5-（碘甲基）噻唑烷-2-硫酮转化为甲硅烷基保护的末端[（乙炔基硫）甲基]取代的噻唑烷-2-硫酮。三（三甲基甲硅烷基）甲基锂与二硫化碳的反应。 提出了一种在无溶剂条件下通过烯丙胺，二硫化碳和碘的多组分反应合成5-（碘甲基）噻唑烷-2-硫酮的有效，环保，简单的一锅法。通过用2,2,2-三（三甲基甲硅烷基）乙二硫酸锂处理，将得到的5-（碘甲基）噻唑烷-2-硫酮转化为甲硅烷基保护的末端[（乙炔基硫）甲基]取代的噻唑烷-2-硫酮。三（三甲基甲硅烷基）甲基锂与二硫化碳的反应。
• Construction of<scp>3‐Azabicyclo</scp>[3.1.0]hexane Backbone by the Reaction of Allenes with Allylamines<i>via</i>Tandem Michael Addition and<scp>Copper‐Mediated</scp>Oxidative Carbanion Cyclization
  作者：Hui Xu、Teng Han、Xiaoyan Luo、Wei‐Ping Deng

  DOI：10.1002/cjoc.202000405

  日期：2021.3

  A facile synthetic method for the construction of 3‐azabicyclo[3.1.0]hexane in the presence of copper catalyst system was developed. The reaction proceeds through Michael addition of allylamines with allenes followed by copper‐mediated intramolecular oxidative carbanion 5‐exo‐trig radical cyclization, affording potential biologically active 3‐azabicyclo[3.1.0]hexane derivatives in moderate to high

  开发了一种在铜催化剂体系存在下构造3-氮杂双环[3.1.0]己烷的简便合成方法。该反应通过将烯丙胺与烯丙基进行迈克尔加成反应，然后进行铜介导的分子内氧化碳负离子5-外-trig自由基环化，以中等至高产率提供潜在的具有生物活性的3-氮杂双环[3.1.0]己烷衍生物（42％-85 ％）。