1-[(2S)-1-methoxy-3-methylbutan-2-yl]-1H-imidazole | 497830-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[(2S)-1-methoxy-3-methylbutan-2-yl]-1H-imidazole
• 英文别名: (S)-1-[1-(hydroxymethyl)-2-methylpropyl]imidazole；L-2-(1-imidazolyl)-3-methylbutanol；rac-(S)-2-(1H-Imidazol-1-yl)-3-methylbutan-1-ol；(2S)-2-imidazol-1-yl-3-methylbutan-1-ol
• CAS: 497830-20-3
• 化学式: C₈H₁₄N₂O
• 分子量: 154.212
• InChiKey: MIBHIRIHFZKRPH-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(2S)-1-methoxy-3-methylbutan-2-yl]-1H-imidazole 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 122.0h， 生成 (S)-1-(1-methoxy-3-methylbutan-2-yl)-3-(2,3,4,5,6-pentamethylbenzyl)-1H-imidazol-3-ium bromide
  参考文献：
  名称：

  Chelating alkoxy NHC–Rh(I) complexes and their applications in the arylation of aldehydes

  摘要：

  In this study, new rhodium(I) complexes (5 and 6) have been prepared by the reaction of [RhCI(COD)](2) with a series of imidazolium salts (3 and 4), which were obtained from a chiral amino alcohol. The catalytic activities of these complexes were tested in the arylation of aldehydes. It was found that the synthesized rhodium complexes were highly effective catalysts for the arylation of aldehydes in short reaction times (5 mm, TOF = 1193 h(-1)). However, the obtained ee values (up to 32% ee) remained low. We have proposed a mechanism for the arylation reaction of aldehydes, which is confirmed via F-19 NMR spectroscopy. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.125
• 作为产物：
  描述：

  (S)-2-(1-imidazolyl)-3-methylbutyricacidethylester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以60%的产率得到1-[(2S)-1-methoxy-3-methylbutan-2-yl]-1H-imidazole
  参考文献：
  名称：

  由天然氨基酸合成手性离子液体。

  摘要：

  首次通过简单，直接的方法从天然氨基酸合成了一个含有一个手性碳（10a-c）的手性咪唑鎓离子液体。手性IL的特性与流行的离子液体非常相似。

  DOI：

  10.1021/jo020503i

文献信息

• Synthesis of Novel Chiral Thioether Ligands Containing Imidazole Rings Based on Natural Amino Acids
  作者：Pu Mao、Yajing Cai、Yongmei Xiao、Liangru Yang、Yuan Xue、Maoping Song

  DOI：10.1080/10426501003671460

  日期：2010.11.23

  Using commercially available natural amino acids (L-Val, L-Leu, L-Phe) as chiral precursors, a series of N-substituted imidazole derivatives containing chiral groups was synthesized from the condensation reaction of amino acids, formaldehyde, glyoxal, and ammonia. Through esterification, reduction, chlorination, and subsequent substitution by thiols, chiral thioethers containing imidazole rings were

  以市售天然氨基酸（L-Val、L-Leu、L-Phe）为手性前体，通过氨基酸、甲醛、乙二醛、氨的缩合反应合成了一系列含有手性基团的N-取代咪唑衍生物. 通过酯化、还原、氯化以及随后的硫醇取代，合成了含有咪唑环的手性硫醚，并优化了合成条件。所有中间体和最终产物均通过 NMR、ESI MS、HR MS 和 IR 进行表征。
• Synthesis of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles from 1,2-amino alcohols
  作者：Yuki Matsuoka、Yasuhiro Ishida、Daisuke Sasaki、Kazuhiko Saigo

  DOI：10.1016/j.tet.2006.05.079

  日期：2006.8

  A highly versatile method for the preparation of enantiopure 1-substituted, 1,2-disubstituted, and 1,4,5-trisubstituted imidazoles was developed by using the cyclocondensation reaction of a 1,2-dicarbonyl compound, an aldehyde, a 1,2-amino alcohol, and ammonium acetate.

  通过使用1,2-二羰基化合物，醛，1,1和1,2-二羰基化合物的环缩合反应，开发了一种高度通用的方法，用于制备对映体纯的1-取代的，1,2-二取代的和1,4,5-三取代的咪唑。 2-氨基醇和乙酸铵。
• Cyclophane-Type Imidazolium Salts with Planar Chirality as a New Class of N-Heterocyclic Carbene Precursors
  作者：Yuki Matsuoka、Yasuhiro Ishida、Daisuke Sasaki、Kazuhiko Saigo

  DOI：10.1002/chem.200800942

  日期：2008.10.20

  Cyclophane-type imidazolium salts with planar chirality were synthesized from enantiopure 2-amino alcohols, of which the N(1) and N(3) positions were connected with a bridge. The structural profiles of the imidazolium salts and their derivative N-heterocyclic carbenes (NHCs) were investigated by means of several analyses. The chiral NHCs derived from these imidazolium salts were found to catalyze the

  由对映体纯的2-氨基醇合成了具有平面手性的环烷型咪唑鎓盐，其中N（1）和N（3）位置通过桥连接。咪唑鎓盐及其衍生物N-杂环卡宾（NHCs）的结构轮廓通过数种分析方法进行了研究。已发现衍生自这些咪唑鎓盐的手性NHC借助烯类的“共轭”蛋白酚催化酮类的α，β-不饱和醛与酮的不对称交叉环化，从而得到具有良好或优异性能的目标γ-内酯对映选择性（高达94％ee）。基于NHC及其中间体的预期结构，以及产品的绝对构型，提出了一种可行的立体控制机制。
• Catalytic activity of chiral chelating <i>N</i>-heterocyclic carbene palladium complexes towards asymmetric allylic alkylation
  作者：Liangru Yang、Yunfei Li、Pu Mao、Jinwei Yuan、Yongmei Xiao

  DOI：10.1080/10426507.2018.1546177

  日期：2019.8.3

  Abstract The catalytic activity of a series of chiral heteroaryl coordinated chelating N-heterocyclic carbene (NHC) palladium complexes towards asymmetric allylic alkylation (AAA) were presented here. The effects of different N-substituents, NHC backbones and chelate rings on the catalytic activity and the enantioselectivity of the alkylation of (E)-1,3-diarylallyl acetates with dialkyl malonate were

  摘要 本文介绍了一系列手性杂芳基配位螯合 N-杂环卡宾 (NHC) 钯配合物对不对称烯丙基烷基化 (AAA) 的催化活性。研究了不同N-取代基、NHC主链和螯合环对(E)-1,3-二芳基烯丙酯乙酸酯与丙二酸二烷基酯烷基化的催化活性和对映选择性的影响。结果表明，在优化条件下，带有吡啶基配位五元螯合环的配合物3a、3b和3i表现出较高的催化活性和手性诱导效率。以高收率和中等ee值获得相应的烷基化产物。此外，发现(E)-1,3-二芳基烯丙基乙酸酯的取代基和亲核试剂的类型也影响结果。
• Modular Synthesis of a New Type of Chiral Bis(carbene) Ligand from <scp>L</scp> ‐Valinol and Iridium(I) and Rhodium(I) Complexes Thereof
  作者：Ulrich Nagel、Claus Diez

  DOI：10.1002/ejic.200800933

  日期：2009.3

  chiral bis(imidazol-2-ylidene) ligands, and their rhodium(I) and iridium(I) complexes, have been prepared by a simple six-step synthesis starting from commercially available enantiomerically pure L-valinol. The stepwise introduction of the imidazoles makes it possible to create chiral bis(NHC) complexes with different substituents at the terminal nitrogen atoms. Formation of IrI and RhI complexes by

  新的手性双 (咪唑-2-亚基) 配体及其铑 (I) 和铱 (I) 配合物已通过简单的六步合成从市售对映体纯 L-缬氨醇开始制备。咪唑的逐步引入可以产生在末端氮原子上具有不同取代基的手性双（NHC）配合物。根据金属和反应条件，通过一锅金属转移反应形成 IrI 和 RhI 配合物会产生不同比例的内型和外型立体异构体。通过结晶获得非对映体纯材料。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)