(1S,2S)-N,N'-1,2-cyclohexanediyl-bis(oxalamic acid ethyl ester) | 910116-80-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S,2S)-N,N'-1,2-cyclohexanediyl-bis(oxalamic acid ethyl ester)
• 英文别名: ethyl 2-[[(1S,2S)-2-[(2-ethoxy-2-oxoacetyl)amino]cyclohexyl]amino]-2-oxoacetate
• CAS: 910116-80-2
• 化学式: C₁₄H₂₂N₂O₆
• 分子量: 314.338
• InChiKey: NIWPYXVEBRHFPJ-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S)-N,N'-1,2-cyclohexanediyl-bis(oxalamic acid ethyl ester) 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 77.0h， 生成
  参考文献：
  名称：

  Synthesis and Crystallographic Characterization of Chiral Bis-oxazoline-amides. Fine-Tunable Ligands for Pd-Catalyzed Asymmetric Alkylations

  摘要：

  New chiral chelating C-2 bis-oxazoline-amide ligands (1) exhibiting a highly flexible molecular structure have been prepared in high yield through a versatile synthetic pathway. Combined crystallographic, variable temperature (VT)-NMR, IR, and ESI-MS studies have been carried out to investigate the nature of the 1-Pd complexes that are effective tools in controlling the stereochemical outcome of Pd-catalyzed allylic alkylations (ee up to 98%).

  DOI：

  10.1021/jo060767v
• 作为产物：
  描述：

  (1S,2S)-(+)-1,2-环己二胺 、 草酰氯单乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以89%的产率得到(1S,2S)-N,N'-1,2-cyclohexanediyl-bis(oxalamic acid ethyl ester)
  参考文献：
  名称：

  Synthesis and Crystallographic Characterization of Chiral Bis-oxazoline-amides. Fine-Tunable Ligands for Pd-Catalyzed Asymmetric Alkylations

  摘要：

  New chiral chelating C-2 bis-oxazoline-amide ligands (1) exhibiting a highly flexible molecular structure have been prepared in high yield through a versatile synthetic pathway. Combined crystallographic, variable temperature (VT)-NMR, IR, and ESI-MS studies have been carried out to investigate the nature of the 1-Pd complexes that are effective tools in controlling the stereochemical outcome of Pd-catalyzed allylic alkylations (ee up to 98%).

  DOI：

  10.1021/jo060767v

文献信息

• Supramolecular structures of bis-thionooxalamic acid esters derived from (±)-cyclohexane-1,2-diamine and (±)-1,2-diphenylethylenediamine
  作者：Barbara Piotrkowska、Tadeusz Połoński、Maria Gdaniec

  DOI：10.1107/s0108270107049797

  日期：2007.12.15

  The bis-thionooxalamic acid esters trans-(+/not superset of)-diethyl N, N'-(cyclohexane-1,2-diyl)bis(2-thiooxamate), C14H22N2O4S2, and (+/not superset of)-N,N'-diethyl (1,2-diphenylethane-1,2-diyl)bis(2-thiooxamate), C22H24N2O4S2, both consist of conformationally flexible molecules which adopt similar conformations with approximate C-2 rotational symmetry. The thioamide and ester parts of the thiooxamate group are significantly twisted along the central C-C bond, with the S = C-C = O torsion angles in the range 30.94 (19) - 44.77 (19)degrees. The twisted s-cis conformation of the thionooxamide groups facilitates assembly of molecules into a one-dimensional polymeric structure via intermolecular three-center C = S center dot center dot center dot NH center dot center dot center dot O = C hydrogen bonds and C-H center dot center dot center dot O interactions formed between molecules of the opposite chirality.
• Synthesis and Crystallographic Characterization of Chiral Bis-oxazoline-amides. Fine-Tunable Ligands for Pd-Catalyzed Asymmetric Alkylations
  作者：Vincenzo Giulio Albano、Marco Bandini、Magda Monari、Eleonora Marcucci、Fabio Piccinelli、Achille Umani-Ronchi

  DOI：10.1021/jo060767v

  日期：2006.8.1

  New chiral chelating C-2 bis-oxazoline-amide ligands (1) exhibiting a highly flexible molecular structure have been prepared in high yield through a versatile synthetic pathway. Combined crystallographic, variable temperature (VT)-NMR, IR, and ESI-MS studies have been carried out to investigate the nature of the 1-Pd complexes that are effective tools in controlling the stereochemical outcome of Pd-catalyzed allylic alkylations (ee up to 98%).
• Molecular self-assembly and optical activity of chiral thionooxalamic acid esters
  作者：Barbara Piotrkowska、Maria J. Milewska、Maria Gdaniec、Tadeusz Połoński

  DOI：10.1016/j.tetasy.2007.06.019

  日期：2007.7

  Three chiral bisthionooxalamides were synthesized by acylation with ethyl or (1R)-menthyl chloroxoacetate of the corresponding diamines and subsequent thionation with Lawesson's reagent. Single crystal X-ray diffraction analysis revealed that products 4b-7b self-assemble in the solid state by the ring [N-H center dot center dot center dot O=C, R-2(2) (10)] or chain [N-H center dot center dot center dot S=C, C(4)] hydrogen-bond motifs. Only in the 2 case of 4b was a helical superstructure formed. In racemic compound 6b, the molecules are connected via N-H center dot center dot center dot S=C hydrogen bonds into homochiral chains, similar to those formed in 7b. The solid state CD spectra of chiral bisthionooxalamides are characterized by strong Cotton effects in the region of the thioamide n-pi* transition. Their sign is determined by the helicity of the S=C-C=O unit. (c) 2007 Elsevier Ltd. All rights reserved.