1-[(1S)-1-苯基乙基]咪唑 | 129696-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-[(1S)-1-苯基乙基]咪唑
• 英文名称: (S)-(-)-[1-phenylethyl]-1H-imidazole
• 英文别名: 1-[(1S)-1-phenylethyl]-1H-imidazole；(S)-N-sec-phenethylimidazole；1-(S)-(phenylethyl)imidazole；S-1-(phenylethyl)imidazole；1-[(1S)-1-phenylethyl]imidazole
• CAS: 129696-60-2
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: ZXIUPWHIKAQKOG-JTQLQIEISA-N

物化性质

• 沸点：
  307.6±11.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[(1S)-1-苯基乙基]咪唑 在 potassium tert-butylate 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 64.0h， 生成 1-[2-(3,5-dimethylpyrazol-1-yl)ethyl]-3-((S)-1-phenylethyl)-3H-imidazol-2-ylidene
  参考文献：
  名称：

  新型NHC配体的分子或胶体钯体系的不同催化行为

  摘要：

  在这项工作中，我们描述了一种新的N-杂环卡宾（NHC）配体的合成，该配体是从杂吡唑-咪唑骨架，即1- [2-（3,5-二甲基吡唑-1-基）乙基] -3衍生而来的-（（S）-1-苯乙基）-3H-咪唑-2-亚烷基（L）。此配体已用作钯（0）纳米粒子（Pd NPs）的有机金属合成的稳定剂。L具有比碳前HLCI对应物更好的稳定效果，允许形成分离的P​​d NP，而HLCl产生聚集的NP。另外，合成并表征了L和HLCl的分子Pd（II）配位化合物，以更好地理解这些配体的配位方式。分子钯和胶体钯体系都已在催化CC偶联过程中得到了进一步测试。根据催化系统，已观察到三种不同类型的反应：i）Suzuki-Miyaura反应是与Pd分子配合物发生的；ii）始终检测到次级反应，即底物的脱卤，并且iii）用胶体催化剂观察到两个溴芳烃分子之间的CC均偶联。

  DOI：

  10.1039/c7dt02729j
• 作为产物：
  描述：

  N-[(1S)-phenylethyl]ethane-1,2-diamine 在 barium permanganate 、 4 A molecular sieve 、 溶剂黄146 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 21.0h， 生成 1-[(1S)-1-苯基乙基]咪唑
  参考文献：
  名称：

  New chiral imidazolinic derivatives

  摘要：

  Novel C-2 substituted 4,5-dihydroimidazoles and imidazoles bearing an N-linked stereogenic group were rapidly prepared from a chiral primary amine. Quaternization of these derivatives resulted in a range of scalemic room temperature ionic liquids. The ability of the imidazolium species to act as reaction medium and/or phase transfer catalyst was also assessed. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.014

文献信息

• Mitsunobu alkylation of imidazole: a convenient route to chiral ionic liquids
  作者：Eun Jin Kim、Soo Y. Ko、Edward K. Dziadulewicz

  DOI：10.1016/j.tetlet.2004.11.144

  日期：2005.1

  The Mitsunobu protocol offers a convenient route from imidazole to N-alkyl-substituted imidazoles, precursors to imidazolium-based ionic liquids, and is particularly useful for preparing chiral ionic liquids.

  Mitsunobu协议提供了从咪唑到N-烷基取代的咪唑（基于咪唑鎓的离子液体的前体）的便捷途径，特别适用于制备手性离子液体。
• Easy preparation of Cp*-functionalized N-heterocyclic carbenes and their coordination to rhodium and iridium
  作者：André Pontes da Costa、Mercedes Sanaú、Eduardo Peris、Beatriz Royo

  DOI：10.1039/b901195a

  日期：——

  A simple high-yielding method for the preparation of a tetramethylcyclopentadienyl-NHC ligand is described. This ligand has been successfully coordinated to Rh and Ir. A related Cp*-NHC ligand with a -CH(2)CMePh- linker between the Cp* and the NHC is also described, together with its coordination to Rh and Ir. This latter ligand, affords the orthocyclometallation of the phenyl ring yielding a constrained

  描述了用于制备四甲基环戊二烯基-NHC配体的简单的高产率方法。该配体已成功配位至Rh和Ir。还描述了在Cp *和NHC之间带有-CH（2）CMePh-接头的相关Cp * -NHC配体，及其与Rh和Ir的配位。后一种配体提供苯环的邻环金属化，从而产生约束结构，其中配体是三齿的。所有配合物均已被充分表征，并描述了其晶体结构。还报道了关于仲醇的β-烷基化和苯胺与伯醇的N-烷基化的初步催化结果。
• Synthesis of novel room temperature chiral ionic liquids: application as reaction media for the heck arylation of aza-endocyclic acrylates
  作者：Julio C. Pastre、Yves Génisson、Nathalie Saffon、Jany Dandurand、Carlos R. D. Correia

  DOI：10.1590/s0103-50532010000500009

  日期：——

  New achiral and chiral RTILs were prepared using novel and/or optimized synthetic routes. These new series of imidazolinium, imidazolium, pyridinium and nicotine-derived ionic liquids were fully characterized including differential scanning calorimetry (DSC) analysis. The performance of these achiral and chiral room temperature ionic liquids (RTILs) was demonstrated by means of the Heck arylation of endocyclic acrylates employing arenediazonium salts and aryl iodides. The Heck arylations performed in the presence of these ionic entities, either as a solvent or as an additive, were effective leading to complete conversion of the substrate and good to excellent yield of the Heck adduct. In spite of the good performances, no asymmetric induction was observed in any of the cases studied. Two new diastereoisomeric NHC-palladium complexes were prepared in good yields from a chiral imidazolium salt and their structure characterized by X-ray diffraction. Overall, the Heck arylations employing arenediazonium tetrafluoroborates in RTILs were more effective than the traditional protocols employing aryl iodides in terms of reactivity and yields.
• A homochiral tripodal receptor with selectivity for sodium (R)-2-aminopropionate over sodium (S)-2-aminopropionate
  作者：Joshua Howarth、Nameer A Al-Hashimy

  DOI：10.1016/s0040-4039(01)01108-x

  日期：2001.8

  This paper describes the synthesis and use o a homochiral tripodal imidazolium salt that can distinguish between sodium (R)-2-aminopropionate and sodium (S)-2-aminopropionate. The imidazolium Salt complexes With the (R) enantiomer but not with the (S) enantiomer. (C) 2001 Elsevier Science Ltd. All rights reserved.
• An investigation of the catalytic potential of mono- and dicationic imidazolium N-heterocyclic carbenes in the benzoin condensation
  作者：Murat Emrah Mavis、Cigdem Yolacan、Feray Aydogan

  DOI：10.1016/j.tetlet.2010.06.099

  日期：2010.8

  The catalytic potential of imidazolium salts in the benzoin condensation was investigated. Various aromatic aldehydes were tested in the benzoin condensation under the optimised protocol to afford alpha-hydroxyketones using N-heterocyclic carbenes derived from mono- and dicationic imidazolium salts. The products were obtained in good yields within short reaction times. Dicationic imidazolium salts with a long aliphatic chain between the imidazole rings were found to be more effective pre-catalysts for the benzoin condensation in comparison to the corresponding monocationic salts having the same aliphatic chain length. (C) 2010 Elsevier Ltd. All rights reserved.