1,2-bis[(2S)-2-carbomethoxy-1-pyrrolidinyl]ethane | 56030-26-3

• 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: 1,2-bis[(2S)-2-carbomethoxy-1-pyrrolidinyl]ethane
• 英文别名: 1,2-bis[2(S)-2-carbomethoxy-1-pyrrolidinyl]ethane；N,N'-ethylenebis((S)-proline) dimethyl ester；N,N'-monoethylene bis-(S)-proline dimethyl ester；methyl (2S)-1-[2-[(2S)-2-methoxycarbonylpyrrolidin-1-yl]ethyl]pyrrolidine-2-carboxylate
• CAS: 56030-26-3
• 化学式: C₁₄H₂₄N₂O₄
• 分子量: 284.356
• InChiKey: CNLWOEWDTCZTCW-RYUDHWBXSA-N

物化性质

• 熔点：
  148-151 °C
• 沸点：
  345.6±42.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-bis[(2S)-2-carbomethoxy-1-pyrrolidinyl]ethane 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 240.0h， 生成
  参考文献：
  名称：

  A dansyl-appended N-heterocycle for Cu2+ and S2− recognition via a displacement mode

  摘要：

  A novel L-proline based heterocycle 3 of C-2 symmetry has been designed and synthesized for cation and anion recognition in aqueous solution. Ligand 3 shows a strong affinity to Cu2+ ion, and their interaction induces a remarkable fluorescence quenching in DMSO:H2O = 9:1 (HEPES buffer, 0.01 M, pH 7.4) among various metal ions. Both the in-situ generated and isolated 3-Cu2+ complex exhibit specific fluorescence recovery upon addition of S2-, even in the presence of S2O32-, L-histidine, and thiol-containing amino acids. For this dual functional switch, a combination of H-1 NMR titration, ESI mass and FT-IR spectra suggest that its sensing behavior is via a displacement mode. Sequential "on-off-on" fluorescence bio-imaging of the heterocycle 3 to Cu2+ and S2- was carried out in HeLa cells. (C) 2018 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2018.11.017
• 作为产物：
  描述：

  草酸醛 、 L-脯氨酸甲酯盐酸盐 在 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以80%的产率得到1,2-bis[(2S)-2-carbomethoxy-1-pyrrolidinyl]ethane
  参考文献：
  名称：

  Convenient Preparation of Optically Active N,N’-Disubstituted Piperazines from Various (S)-α-Amino Acid Esters

  摘要：

  在 2 摩尔当量的氰硼氢化钠存在下，将 1 摩尔当量的 N,N'-单乙烯-双(S)-δ-氨基酸二酯二盐酸盐与 1 摩尔当量的乙二醛在甲醇中反应，制备出 N,N,N',N'-二乙烯双(S)-δ-氨基酸二酯二盐酸盐（哌嗪衍生物），收率为 70-80%。使用乙二醛和氰基硼氢化钠从(S)-δ-氨基酸酯盐酸盐中也可以得到类似的前体，产率为 70-80%。

  DOI：

  10.1055/s-1996-4245

文献信息

• Synthesis of Novel L‐Proline Derived Macrocyclic Dioxopolyamines of C₂Symmetry
  作者：Xuemei Yang、Baohua Li、Enqin Fu

  DOI：10.1081/scc-200048458

  日期：2005.1

  A short and convenient synthesis for four novel chiral L‐proline derived macrocyclic dioxopolyamines of C2 symmetry, by condensation of appropriate diester intermediates and polyamines, is reported. These macrocyclic dioxopolyamines may be applied as chiral solvating agents for enantiomeric recognition, and the work also provided a simple and convenient way for the synthesis of the diester intermediates

  摘要 报道了通过适当的二酯中间体和多胺的缩合，短而方便地合成了四种新型手性 L-脯氨酸衍生的 C2 对称的大环二氧多胺。这些大环二氧多胺可作为手性溶剂化剂用于对映体识别，该工作也为二酯中间体的合成提供了一种简便的途径。
• Novel rigid chiral macrocyclic dioxopolyamines derived from l-proline as chiral solvating agents for carboxylic acids
  作者：Xuemei Yang、Xiaojun Wu、Maohai Fang、Quan Yuan、Enqin Fu

  DOI：10.1016/j.tetasy.2004.07.016

  日期：2004.8

  NMR was employed to investigate the chiral recognition ability of two novel l-proline derived rigid chiral macrocyclic dioxopolyamines, (12S)-1,4,7,10-tetraazadicyclo[10.3.0]pentadecane-3,11-dione 1 and (8S,18S)-1,4,10,13,16-pentaazatricyclo[16.3.0.04,8]heneicosane-9,17-dione 2, the latter of which is newly synthesized. The crystal structures of the two macrocyclic compounds were determined by X-ray

  1 H NMR用于研究两种新型的l-脯氨酸衍生的刚性手性大环二氧杂多胺（（12 S）-1,4,7,10-四氮二环[10.3.0] pentadecane-3,11-dione 1的手性识别能力（8 S，18 S）-1,4,10,13,16-五氮杂三环[16.3.0.0 4,8 ] heneicosane-9,17-dione 2，后者是新合成的。通过X射线单晶结构分析确定两种大环化合物的晶体结构。乔布图表明化合物1与（R）-或（S）-扁桃酸形成1：1瞬时络合物，而化合物2与上面的两个客人组成一个1：2的瞬间复合体。通过非线性最小二乘拟合法确定化合物1与（R）-和（S）-扁桃酸的缔合常数。对于我们选择的外消旋羧酸的对映异构体，两个大环均表现出良好的手性识别能力。结果表明，大环dioxopolyamine Ç 2对称性具有比的对映异构体更好识别能力Ç 1对称性。
• Syntheses and crystal structures of oxovanadium(IV) complexes with N,N′-ethylenebis(amino acids)
  作者：Kenji Kawabe、Makoto Tadokoro、Ken Hirotsu、Naohisa Yanagihara、Yoshitane Kojima

  DOI：10.1016/s0020-1693(00)00134-1

  日期：2000.7

  The oxovanadium(IV) complexes with N,N′-ethylenebis(amino acids) ([VO(XeX)(H2O)], where X=A ((S)-Ala), V ((S)-Val) and P ((S)-Pro)) are synthesized and characterized by X-ray analyses and IR spectra. The crystal structure analyses reveal that the geometry around the vanadium cation of each complex is distorted octahedral and is coordinated by a water molecule and the tetradentate N,N′-ethylenebis(amino

  氧钒（IV）与N，N'-亚乙基双（氨基酸）（[VO（XeX）（H 2 O）]，其中X = A（（S）-Ala），V（（S -Val）通过X射线分析和IR光谱合成和表征P和（（S）-Pro））。晶体结构分析表明，每个络合物的钒阳离子周围的几何形状都呈八面体形，并由水分子和具有Δ-顺式-α构型的四齿N，N'-亚乙基双（氨基酸）阴离子配位，其中水氧原子占据赤道配位位置，每个四齿配体的两个仲或叔氮原子之一被反式键合钒氧羰基部分。目前和以前的含氮和氧的配体的VO配合物的键长汇编表明，PeP配体的叔胺基延长了VN键。比较三个五元环（一个乙二胺环和两个氨基酸环）的键角之和表明，环应变主要集中在乙二胺环中，而氨基酸环的应变位于V的赤道面上（IV）离子比另一个氨基酸环中的离子更显着。本发明配合物的红外观察与它们的晶体学研究非常一致。
• STRASAK, M.;MAJER, J.
  作者：STRASAK, M.、MAJER, J.

  DOI：——

  日期：——
• A dansyl-appended N-heterocycle for Cu2+ and S2− recognition via a displacement mode
  作者：Xu Wang、Peng Xia、Xiaohuan Huang

  DOI：10.1016/j.saa.2018.11.017

  日期：2019.3

  A novel L-proline based heterocycle 3 of C-2 symmetry has been designed and synthesized for cation and anion recognition in aqueous solution. Ligand 3 shows a strong affinity to Cu2+ ion, and their interaction induces a remarkable fluorescence quenching in DMSO:H2O = 9:1 (HEPES buffer, 0.01 M, pH 7.4) among various metal ions. Both the in-situ generated and isolated 3-Cu2+ complex exhibit specific fluorescence recovery upon addition of S2-, even in the presence of S2O32-, L-histidine, and thiol-containing amino acids. For this dual functional switch, a combination of H-1 NMR titration, ESI mass and FT-IR spectra suggest that its sensing behavior is via a displacement mode. Sequential "on-off-on" fluorescence bio-imaging of the heterocycle 3 to Cu2+ and S2- was carried out in HeLa cells. (C) 2018 Elsevier B.V. All rights reserved.