1-(4-氟苯基)-2-丙炔-1-胺 | 226698-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-氟苯基)-2-丙炔-1-胺
• 英文名称: (+/-)-1-(4-fluorophenyl)-2-propynylamine
• 英文别名: 1-(4-Fluorophenyl)prop-2-yn-1-amine
• CAS: 226698-96-0
• 化学式: C₉H₈FN
• mdl: MFCD18825395
• 分子量: 149.168
• InChiKey: WVPIGYWIRWLMMC-UHFFFAOYSA-N

物化性质

• 沸点：
  211.9±25.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基)-2-丙炔-1-胺 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 Candida antarctica lipase 作用下， 以 甲苯 为溶剂， 生成 (R)-2-[(acetamino)(4-fluorophenyl)methyl]-1,3-butadiene
  参考文献：
  名称：

  Microwave-assisted ethylene–alkyne cross-metathesis: synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes

  摘要：

  Chiral 1-arylpropargyl amides, which are resistant to undergoing ethylene-alkyne cross-metathesis at atmospheric pressure, were reacted under microwave irradiation to afford enantiomerically enriched 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes within a few minutes. Enantiomerically enriched amides underwent ethylene-alkyne cross-metathesis with retention of configuration at the propargylic/allylic position. A series of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes were synthesised with ee >= 95%; these latter compounds could be used as building blocks for the synthesis of new antifungal and antiaromatase agents. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.002
• 作为产物：
  描述：

  (+/-)-N-[1-(4-fluorophenyl)-2-propynyl]acetamide 在 盐酸 作用下， 生成 1-(4-氟苯基)-2-丙炔-1-胺
  参考文献：
  名称：

  微波辅助点击化学合成对映体纯的α-[4-（1-取代）-1,2,3-三唑-4-基]-苄基乙酰胺：寻求新的潜在抗微生物剂

  摘要：

  手性1-苯基-2-丙炔基胺是合成与联苯苄唑有关的抗真菌剂和抗芳香酶的重要组成部分。在此报告中，已采用微波辅助的Cu（I）催化的“点击化学”方法轻松生成对映体纯的α-[4-（1-取代）-1,2,3-三唑-从外消旋炔丙基胺开始的4-基]苄基乙酰胺。这些化合物可以代表用于合成新的抗微生物剂的容易获得的中间体。

  DOI：

  10.1016/j.tetasy.2007.06.007

文献信息

• Synthesis of enantiomerically pure α-[4-(1-substituted)-1,2,3-triazol-4-yl]-benzylacetamides via microwave-assisted click chemistry: towards new potential antimicrobial agents
  作者：Daniele Castagnolo、Filippo Dessì、Marco Radi、Maurizio Botta

  DOI：10.1016/j.tetasy.2007.06.007

  日期：2007.6

  Chiral 1-phenyl-2-propynylamines are important building blocks for the synthesis of antifungal and antiaromatase agents related to bifonazole. In this report, a microwave-assisted Cu(I)-catalyzed ‘click chemistry’ approach has been employed to easily generate a small library of enantiomerically pure α-[4-(1-substituted)-1,2,3-triazol-4-yl]benzylacetamides starting from racemic propargylamines. These

  手性1-苯基-2-丙炔基胺是合成与联苯苄唑有关的抗真菌剂和抗芳香酶的重要组成部分。在此报告中，已采用微波辅助的Cu（I）催化的“点击化学”方法轻松生成对映体纯的α-[4-（1-取代）-1,2,3-三唑-从外消旋炔丙基胺开始的4-基]苄基乙酰胺。这些化合物可以代表用于合成新的抗微生物剂的容易获得的中间体。
• Resolution of (±)-1-Aryl-2-propynylamines via Acyltransfer Catalyzed by <i>Candida antarctica</i> Lipase
  作者：Flavia Messina、Maurizio Botta、Federico Corelli、Manfred P. Schneider、Fabio Fazio

  DOI：10.1021/jo982513i

  日期：1999.5.1
• Metal-Free Cascade Approach toward Polysubstituted Indolizines from Chromone-Based Michael Acceptors
  作者：Thomas Lepitre、Raphael Le Biannic、Mohamed Othman、Ata Martin Lawson、Adam Daïch

  DOI：10.1021/acs.orglett.7b00309

  日期：2017.4.21

  An efficient cascade transformation toward indolizine-based molecules has been developed. This process leads to the rapid construction of two C-N bonds and one C-C bond without the need of any metal catalysis. The approach involves easily accessible chromone-based Michael acceptors and propargylamine derivatives as starting materials. This cascade constitutes a novel and very competitive alternative to the well reported strategies using pyridine or pyrrole derivatives for accessing the indolizine ring with substituents at uncommon C-positions
• Microwave-assisted ethylene–alkyne cross-metathesis: synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes
  作者：Daniele Castagnolo、Michela L. Renzulli、Elena Galletti、Federico Corelli、Maurizio Botta

  DOI：10.1016/j.tetasy.2005.08.002

  日期：2005.9

  Chiral 1-arylpropargyl amides, which are resistant to undergoing ethylene-alkyne cross-metathesis at atmospheric pressure, were reacted under microwave irradiation to afford enantiomerically enriched 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes within a few minutes. Enantiomerically enriched amides underwent ethylene-alkyne cross-metathesis with retention of configuration at the propargylic/allylic position. A series of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes were synthesised with ee >= 95%; these latter compounds could be used as building blocks for the synthesis of new antifungal and antiaromatase agents. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of pyrazino[1,2-<i>b</i>]indazoles <i>via</i> cascade cyclization of indazole aldehydes with propargylic amines
  作者：Zeng-Hui Wu、Heng-Tong Qu、Ben-Jun Han、Jia-Xin Yang、Xiang-Wei Chang、Cheng-Tao Feng

  DOI：10.1039/d4ob00051j

  日期：——

  An efficient intermolecular annulation of indazole aldehydes with propargylic amines has been developed for the synthesis of pyrazinoindazoles under catalyst- and additive-free conditions. This straightforward methodology was found to feature a wide substrate scope, high atom economy and environmental advantages. The bioactivity results of these new pyrazino[1,2-b]indazoles showed that some of them

  已经开发出吲唑醛与炔丙胺的有效分子间成环反应，用于在无催化剂和添加剂的条件下合成吡嗪并吲唑。人们发现这种简单的方法具有底物范围广、原子经济性高和环境优势的特点。这些新型吡嗪并[1,2- b ]吲唑类化合物的生物活性结果表明，其中一些化合物表现出显着的抗真菌活性。