(Z)-N1-((R)-1-hydroxy-3-methylbutan-2-yl)-N3-((S)-1-hydroxy-3-methylbutan-2-yl)-2-(thiophen-2-ylmethylene)malonamide | 1201653-12-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (Z)-N1-((R)-1-hydroxy-3-methylbutan-2-yl)-N3-((S)-1-hydroxy-3-methylbutan-2-yl)-2-(thiophen-2-ylmethylene)malonamide
• 英文别名: (S,S)-N,N'-bis(2-hydroxy-1-isopropyl)-2-(2-thienylmethylidene)malonamide
• CAS: 1201653-12-4
• 化学式: C₁₈H₂₈N₂O₄S
• 分子量: 368.497
• InChiKey: UNEJLXCJIYVDSS-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  98.66
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (Z)-N1-((R)-1-hydroxy-3-methylbutan-2-yl)-N3-((S)-1-hydroxy-3-methylbutan-2-yl)-2-(thiophen-2-ylmethylene)malonamide 在 劳森试剂 、 咪唑 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Synthesis of heteroarylidene malonate derived bis(thiazolines) and their application in the catalyzed Friedel–Crafts reaction

  摘要：

  A series of novel heteroarylidene malonate derived bis(thiazoline) ligands 1 and 2 were synthesized and applied to a Friedel-Crafts reaction between indole and alkylidene malonate. The Cu(OTf)(2) complex of ligand 2b bearing a benzyl group afforded moderate to excellent enantioselectivity for the adducts (up to >99% ee). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.003
• 作为产物：
  描述：

  2-(2-噻吩亚甲基)丙二酸二乙酯 在 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (Z)-N1-((R)-1-hydroxy-3-methylbutan-2-yl)-N3-((S)-1-hydroxy-3-methylbutan-2-yl)-2-(thiophen-2-ylmethylene)malonamide
  参考文献：
  名称：

  Synthesis of heteroarylidene malonate derived bis(thiazolines) and their application in the catalyzed Friedel–Crafts reaction

  摘要：

  A series of novel heteroarylidene malonate derived bis(thiazoline) ligands 1 and 2 were synthesized and applied to a Friedel-Crafts reaction between indole and alkylidene malonate. The Cu(OTf)(2) complex of ligand 2b bearing a benzyl group afforded moderate to excellent enantioselectivity for the adducts (up to >99% ee). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.003

文献信息

• Synthesis, Characterization and Antimicrobial Activity of Novel Pharmacophores Incorporating Imidazoline-Oxazoline Scaffold
  作者：Assem Barakat、Abdullah Mohammed Al-Majid、Faisal M. Al-Qahatany、Mohammad Shahidul Islam、Mohamed H.M. Al-Agamy

  DOI：10.5012/bkcs.2014.35.2.562

  日期：2014.2.20

  In this work, synthesis, characterization and antimicrobial activity of series of imidazolines-oxazolines scaffolds 5a-f and 10a-d have been investigated. All the imidazolines-oxazolines derivatives were prepared from acid derivatives 1 and 6a-c, and enantiomerically pure (S)-2-amino-3-methyl-1-butanol in four steps with excellent optical purity. The structures of all newly synthesized compounds have been elucidated by $^1H$, $^13}C$ NMR, GCMS, and IR spectrometry. Their purity was confirmed using elemental analysis. Some newly synthesized compounds were examined to in-vitro antimicrobial activity. Among the prepared products 10d was found to exhibits the most active against all tested bacteria and fungi with minimal inhibitory concentration (MIC) ranged between 21.9 and $42.6\mu}g/mL$.

  在本研究中，合成、表征及一系列咪唑啉-噁唑啉骨架5a-f和10a-d的抗微生物活性进行了探讨。所有咪唑啉-噁唑啉衍生物均由酸类衍生物1和6a-c以及对映体纯净的(S)-2-氨基-3-甲基-1-丁醇经过四步反应合成，且具有极好的光学纯度。所有新合成化合物的结构通过^1H NMR、^13C NMR、GCMS和IR光谱进行了解释。它们的纯度通过元素分析得到确认。部分新合成的化合物进行了体外抗微生物活性测试。在所制备的产品中，10d被发现对所有测试的细菌和真菌具有最高的活性，最小抑菌浓度（MIC）范围为21.9至42.6 μg/mL。
• Highly Enantioselective Friedel–Crafts Reaction of Indole with Alkylidenemalonates Catalyzed by Heteroarylidene Malonate-Derived Bis(oxazoline) Copper(II) Complexes
  作者：Yan-Jin Sun、Nan Li、Zhong-Bo Zheng、Lei Liu、Yan-Bo Yu、Zhao-Hai Qin、Bin Fu

  DOI：10.1002/adsc.200900669

  日期：2009.12

  A series of cheap and easily accessible heteroarylidenemalonate-derived bis(oxazoline) ligands 1 and 2 were synthesized and their copper(II) complexes were applied to the catalytic Friedel–Crafts reaction between indoles and diethyl alkylidenemalonates, Excellent asymmetric enantioselectivities were afforded for the S-enantiomer (up to >99% ee) in isobutyl alcohol, and the R-enantiomer (up to 96.5%

  合成了一系列廉价且易于获得的杂芳基丙二酸酯衍生的双（恶唑啉）配体1和2，并将它们的铜（II）配合物用于吲哚和烷基亚乙基丙二酸酯之间的Friedel-Crafts催化反应，S具有出色的不对称对映选择性-对映异构体（最高> 99％ee）在异丁醇中，R-对映异构体（最高96.5％ee）在二氯甲烷中。