(S,S)-N,N'-bis(2-hydroxy-1-benzyl)-2-(2-thienylmethylidene)malonamide | 1201653-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S,S)-N,N'-bis(2-hydroxy-1-benzyl)-2-(2-thienylmethylidene)malonamide
• CAS: 1201653-17-9
• 化学式: C₂₆H₂₈N₂O₄S
• 分子量: 464.585
• InChiKey: PSLXSPPWDUDHFI-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  (S,S)-N,N'-bis(2-hydroxy-1-benzyl)-2-(2-thienylmethylidene)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 N1,N3-bis((S)-1-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-2-yl)-2-(thiophen-2-ylmethylene)propanebis(thioamide)
  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 (S,S)-N,N'-bis(2-hydroxy-1-benzyl)-2-(2-thienylmethylidene)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

• 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。