(E)-N-(3-phenyl-2-propenyl)-1-naphthalenamine | 98978-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N-(3-phenyl-2-propenyl)-1-naphthalenamine
• 英文别名: trans-N-cinnamylnaphthalen-1-amine；N-(3-phenylallyl)-1-naphthylamine；N-[(E)-3-phenylprop-2-enyl]naphthalen-1-amine
• CAS: 98978-53-1
• 化学式: C₁₉H₁₇N
• 分子量: 259.351
• InChiKey: CYLXFMNXWCACBH-JXMROGBWSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  465.3±24.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  (E)-N-(3-phenyl-2-propenyl)-1-naphthalenamine 以9%的产率得到
  参考文献：
  名称：

  INADA SEISAKU; KURATA RYU-ICHIRO, BULL. CHEM. SOC. JAP., 1981, 54, NO 5, 1581-1582

  摘要：

  DOI：
• 作为产物：
  描述：

  3-苯基丙-2-烯-1-醇 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 吡啶 、 三乙烯二胺 、 (R)-1-naphthyl chiral phosphoramidite 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 (E)-N-(3-phenyl-2-propenyl)-1-naphthalenamine
  参考文献：
  名称：

  原位生成活化的环金属化铱催化剂后，芳香胺的对映选择性烯丙基化。

  摘要：

  DOI：

  10.1002/anie.200460276

文献信息

• Direct and indirect reductive amination of aldehydes and ketones with solid acid-activated sodium borohydride under solvent-free conditions
  作者：Byung Tae Cho、Sang Kyu Kang

  DOI：10.1016/j.tet.2005.04.039

  日期：2005.6

  A simple and convenient procedure for reductive amination of aldehydes and ketones using sodium borohydride activated by boric acid, p-toluenesulfonic acid monohydrate or benzoic acid as reducing agent under solvent-free conditions is described.

  描述了一种简单方便的程序，用于在无溶剂条件下，使用硼酸，对甲苯磺酸一水合物或苯甲酸作为还原剂活化的硼氢化钠还原性胺化醛和酮。
• Magnetite (Fe3O4) silica based organic–inorganic hybrid copper(ii) nanocatalyst: a platform for aerobic N-alkylation of amines
  作者：Rakesh K. Sharma、Yukti Monga、Aditi Puri、Garima Gaba

  DOI：10.1039/c3gc40818c

  日期：——

  A magnetically recoverable, efficient and selective copper based nanocatalyst has been synthesised via covalent grafting of 2-acetylthiophene on a silica coated magnetic nanosupport followed by metallation with copper acetate. The obtained organic–inorganic hybrid nanomaterial has been characterized by electron microscopy techniques (SEM and TEM with EDS), XRD, VSM, FT-IR and AAS. The catalytic performance of the novel nano-catalyst is evaluated in the active transformation of various aromatic amines to industrially-important alkylated amines. The nanocomposites afford high turnover frequency and high selectivity for amines under aerobic conditions. Furthermore, the heterogeneous nature of the catalyst allows easy magnetic recovery and regeneration, which makes the present protocol highly beneficial to address the industrial needs and environmental concerns.

  通过共价接枝2-乙酰噻吩于涂覆二氧化硅的磁性纳米载体上，随后以乙酸铜进行金属化处理，成功合成了一种磁性可回收、高效且选择性的铜基纳米催化剂。该获得的有机-无机杂化纳米材料通过电子显微技术（SEM和TEM配备EDS）、XRD、VSM、FT-IR和AAS进行了表征。这种新型纳米催化剂的催化性能在多种芳香胺向工业重要的烷基化胺的活性转化过程中得到了评估。在有氧条件下，纳米复合材料表现出高周转频率和高胺类选择性。此外，催化剂的非均质性质使得其易于通过磁性进行回收和再生，这使得本协议在满足工业需求和环境关切方面具有高度益处。
• Direct palladium(0)-catalyzed amination of allylic alcohols with aminonaphthalenes
  作者：Yi-Jen Shue、Shyh-Chyun Yang、Hwe-Chen Lai

  DOI：10.1016/s0040-4039(02)02861-7

  日期：2003.2

  The direct activation of CO bonds in allylic alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium reagents. The palladium-catalyzed amination of allylic alcohols using aminonaphthalenes gave N-allylic naphthylamines in good yields. The monoallylation products are formed in the main.

  通过在钛试剂的存在下进行反应，已经加速了钯配合物在烯丙基醇中对CO键的直接活化。使用氨基萘的钯催化的烯丙基醇的胺化以良好的收率得到了N-烯丙基萘胺。单烯丙基化产物在主体中形成。
• Synthesis and structure-activity relationships of naftifine-related allylamine antimycotics
  作者：Anton Stuetz、Apostolos Georgopoulos、Waltraud Granitzer、Gabor Petranyi、Daniel Berney

  DOI：10.1021/jm00151a019

  日期：1986.1

  Naftifine (1) is the first representative of the new antifungal allylamine derivatives. Its biological activity is strictly bound to specific structural requirements that are unrelated to those of known antifungals. A tertiary allylamine function seems to be a prerequisite for activity against fungi. By systematic variation of the individual structural elements in 1, detailed structure-activity relationships are defined in which the phenyl ring is the structural feature permitting the widest variations. Versatile synthetic routes to allylamine derivatives and comparative biological data are presented.
• A Convenient and Efficient Route for the Allylation of Aromatic Amines and α-Aryl Aldehydes with Alkynes in the Presence of a Pd(0)/PhCOOH Combined Catalyst System
  作者：Nitin T. Patil、Huanyou Wu、Isao Kadota、Yoshinori Yamamoto

  DOI：10.1021/jo0485684

  日期：2004.12.1

  The allylation of aromatic amines with alkynes proceeded smoothly in the presence of catalytic amounts of Pd(PPh3)(4) and benzoic acid. The allylation products were obtained in high yields in a regio- and stereoselective manner. The effect of various groups on the nitrogen atom of anilines was studied. Regardless of the substituent (electron withdrawing or electron donating) on the aromatic ring, the reaction proceeded well. Various functionalities, including -CH3, -OMe, -Cl, -CN, -COOMe, -NO2 and -COCH3 were tolerated under the reaction conditions. Similarly, the allylation of alpha-aryl aldehydes proceeded well with the same level of regio- and stereoselectivity as the allylation of aromatic amines. This reaction provides the second example of the transition metal catalyzed direct alpha-allylation of aldehydes.