N-(3-苯基-2-丙炔-1-基)-2-丙烯-1-胺 | 98729-78-3

• 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: N-(3-苯基-2-丙炔-1-基)-2-丙烯-1-胺
• 英文名称: N-(3-phenylprop-2-yn-1-yl)prop-2-en-1-amine
• 英文别名: N-allyl-N-(3-phenyl-2-propynyl)amine；N-(3-Phenyl-2-propyn-1-YL)-2-propen-1-amine；3-phenyl-N-prop-2-enylprop-2-yn-1-amine
• CAS: 98729-78-3
• 化学式: C₁₂H₁₃N
• mdl: MFCD07406324
• 分子量: 171.242
• InChiKey: KPEAJUQUCTYDHB-UHFFFAOYSA-N

物化性质

• 沸点：
  271.3±23.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  N-(3-苯基-2-丙炔-1-基)-2-丙烯-1-胺 在 di(rhodium)tetracarbonyl dichloride 三乙胺 作用下， 以 二氯甲烷 、 二丁醚 为溶剂， 反应 16.58h， 生成 6-phenyl-2-(toluene-4-sulfonyl)-2,3,3a,4-tetrahydro-1H-cyclopenta[c]pyrrol-5-one
  参考文献：
  名称：

  The rhodium-catalyzed Pauson–Khand reaction

  摘要：

  A rhodium carbonyl complex, [RhCl(CO)(2)](2), serves as a catalyst of the intra- and inter-molecular Pauson-Khand reaction. By the use of the rhodium catalyst, cyclopentenone derivatives are prepared from various 1,6- and 1,7-enynes under 1 arm of CO. Furthermore, this rhodium-catalyzed reaction is accelerated by reducing partial pressure of CO to less than 1 atm. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00835-4
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-醇 在 溴 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(3-苯基-2-丙炔-1-基)-2-丙烯-1-胺
  参考文献：
  名称：

  铑-双苯并二恶英膦复合物催化的醇溶剂均相对映选择性鲍森-坎德型环化反应

  摘要：

  发现手性阻转异构二膦配体（S）-双苯并二恶烷膦在醛脱羰和级联对映选择性Pauson-Khand型反应的合作过程中非常有效。各种1,6-烯炔以良好的收率和对映体过量（最高ee为96％）转化为相应的双环环戊烯酮。这种新的Rh催化均相双重催化系统的吸引人之处在于该反应可以在酒精溶液中进行。

  DOI：

  10.1002/adsc.200505105

文献信息

• Rhodium-Catalyzed Asymmetric Aqueous Pauson-Khand-Type Reaction
  作者：Fuk Yee Kwong、Yue Ming Li、Wai Har Lam、Liqin Qiu、Hang Wai Lee、Chi Hung Yeung、Kin Shing Chan、Albert S. C. Chan

  DOI：10.1002/chem.200401237

  日期：2005.6.20

  operationally simple protocol allows both catalyst and reactants to be handled under air without precautions. Various enynes were transformed to the corresponding bicyclic cyclopentenones in good yield and enantiomeric excess (up to 95 % ee). A study of the electronic effects of the enyne substrates revealed a correlation between the electronic properties of the substrates and the ee value obtained in

  开发了一种有趣的铑催化的不对称含水Pauson-Khand型反应。发现手性阻转异构体二吡啶基二膦配体在该系统中是高度有效的。该操作简单的方案允许催化剂和反应物都在空气中进行处理而无需采取预防措施。将各种烯炔以良好的收率和对映体过量（至多95％ee）转化为相应的双环环戊烯酮。对烯炔底物的电子效应的研究表明，底物的电子性质与Pauson-Khand型反应产物中获得的ee值之间存在相关性。从Hammett研究中观察到线性自由能关系。
• Microwave‐Assisted Rhodium‐Complex‐Catalyzed Cascade Decarbonylation and Asymmetric Pauson–Khand‐Type Cycli­zations
  作者：Hang Wai Lee、Lai Na Lee、Albert S. C. Chan、Fuk Yee Kwong

  DOI：10.1002/ejoc.200800272

  日期：2008.7

  Microwave-assisted Rh–diphosphane-complex-catalyzed dual catalysis is reported. This cooperative process provides [2+2+1] cycloadducts by sequential decarbonylation of aldehyde or formate and carbonylation of enynes within a short period of time. Various O-, N-, and C-tethered enynes were transformed into the corresponding products in good yields. The first enantioselective version of this microwave-accelerated

  报道了微波辅助的 Rh-二膦复合物催化的双催化。这种协同过程通过醛或甲酸酯的顺序脱羰和烯炔的羰基化在短时间内提供 [2+2+1] 环加合物。各种O-、N-和C-系链烯炔以良好的产率转化为相应的产品。实现了这种微波加速级联环化的第一个对映选择性版本。在手性 Rh-(S)-bisbenzodioxanPhos 络合物的存在下，环戊烯酮产品的 ee 值高达 90%。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• Diversity-oriented heterocyclic synthesis using divergent reactivity of N-substituted iso(thio)cyanates
  作者：Jean-François Vincent-Rocan、Joshua S. Derasp、André M. Beauchemin

  DOI：10.1039/c5cc07212c

  日期：——

  Carbon-substituted isocyanates and isothiocyanates are common building blocks in organic synthesis. In contrast, synthetic uses of N-substituted isocyanates and isothiocyanates are severely underdeveloped: few have been reported and their reactivity...

  碳取代的异氰酸酯和异硫氰酸酯是有机合成中常见的组成部分。相比之下，N-取代的异氰酸酯和异硫氰酸酯的合成用途严重不发达：几乎没有报道，并且它们的反应性...
• Iridium-catalyzed cascade decarbonylation/highly enantioselective Pauson–Khand-type cyclization reactions
  作者：Fuk Yee Kwong、Hang Wai Lee、Wai Har Lam、Liqin Qiu、Albert S.C. Chan

  DOI：10.1016/j.tetasy.2006.03.036

  日期：2006.4

  An easily accessible chiral iridium-BINAP complex can effect the cooperative processes of decarbonylation of an aldehyde and cascaded enantioselective Pauson-Khand-type reaction. A survey of ligands revealed that atropisomeric aryl-diphosphine ligands were superior to chiral alkyl-diphosphines in this dual catalysis. Applying the reaction conditions of [IrCl(COD)](2)/(S)-BINAP complex with nonylaldehyde as a CO surrogate at 100 degrees C in anhydrous dioxane solvent, various 1,6-enynes were transformed to the corresponding optically active bicyclic cyclopentenones with excellent enantioselectivities (up to 98% ee). (c) 2006 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Aerobic Intramolecular Carbo- and Amino-Oxygenation of Alkynes for Synthesis of Azaheterocycles
  作者：Kah Kah Toh、Stephen Sanjaya、Sophian Sahnoun、Sin Yee Chong、Shunsuke Chiba

  DOI：10.1021/ol3007106

  日期：2012.5.4

  A synthetic method of highly substituted quinolines has been developed from N-(2-alkynylaryl)enamine carboxylates under Cu-catalyzed aerobic conditions via intramolecular carbo-oxygenation of alkynes. This strategy was further applied for N-alkynylamidines for amino-oxygenation of alkynes, leading to imidazole and quinazoline derivatives.