(R,R)-N,N-bis(2-hydroxy-1-phenylethyl)ethanediamide | 649551-38-2

• 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: (R,R)-N,N-bis(2-hydroxy-1-phenylethyl)ethanediamide
• 英文别名: N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]ethanediamide；N~1~,N~2~-Bis[(1R)-2-hydroxy-1-phenylethyl]ethanediamide；N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]oxamide
• CAS: 649551-38-2
• 化学式: C₁₈H₂₀N₂O₄
• 分子量: 328.368
• InChiKey: UVLNKDDDIQAUAY-HOTGVXAUSA-N

物化性质

• 熔点：
  226-227 °C
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,R)-N,N-bis(2-hydroxy-1-phenylethyl)ethanediamide 在 sodium hydroxide 、 氯化亚砜 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成 (4R,4R)-4,4-二苯基-4,4,5,5-四氢-2,2-双噁唑
  参考文献：
  名称：

  A new photoluminescent CuI2N6 chromophore

  摘要：

  一种新型 CuI2N6 发色团与 2,2′-双[(4R)-苯基]-1,3-噁唑啉（L）分离在光学纯的三链螺旋[Cu2L3](ClO4)2 中，该发色团在甲醇中于室温下显示光致发光（发射最大值 λem = 385 nm；量子产率 ϕ = 1.6 × 10-4；寿命 τ≈ 2 ns），以及在 77 K 时（λem = 430 nm；τ = 0.89 ± 0.13 s）。

  DOI：

  10.1039/b105442m
• 作为产物：
  描述：

  草酸二甲酯 、 D-苯甘氨醇 以 甲醇 为溶剂， 反应 0.5h， 以98%的产率得到(R,R)-N,N-bis(2-hydroxy-1-phenylethyl)ethanediamide
  参考文献：
  名称：

  锰催化不对称转移氢化使用手性草酰胺配体的酮

  摘要：

  探索了在新型锰催化剂存在下使用异丙醇 (IPA) 作为氢供体的酮的不对称转移氢化。选择性和活性系统很容易由 [MnBr(CO)5] 和廉价的 C 2 对称双草酰胺配体原位生成。在优化的反应条件下，Mn 衍生的催化剂与相关的钌催化剂相比具有更高的对映选择性。

  DOI：

  10.1055/s-0037-1611669
• 作为试剂：
  描述：

  4-甲基-2-戊酮 在 五羰基溴化锰(I) 、 potassium tert-butylate 、 异丙醇 、 (R,R)-N,N-bis(2-hydroxy-1-phenylethyl)ethanediamide 作用下， 反应 20.0h， 生成 (S)-(+)-4-甲基-2-戊醇 、 (R)-(-)-4-甲基-2-戊醇
  参考文献：
  名称：

  锰催化不对称转移氢化使用手性草酰胺配体的酮

  摘要：

  探索了在新型锰催化剂存在下使用异丙醇 (IPA) 作为氢供体的酮的不对称转移氢化。选择性和活性系统很容易由 [MnBr(CO)5] 和廉价的 C 2 对称双草酰胺配体原位生成。在优化的反应条件下，Mn 衍生的催化剂与相关的钌催化剂相比具有更高的对映选择性。

  DOI：

  10.1055/s-0037-1611669

文献信息

• Chiral Bis(amino alcohol)oxalamide Gelators—Gelation Properties and Supramolecular Organization: Racemate versus Pure Enantiomer Gelation
  作者：Janja Makarević、Milan Jokić、Zlata Raza、Zoran Štefanić、Biserka Kojić-Prodić、Mladen Žinić

  DOI：10.1002/chem.200304573

  日期：2003.11.21

  Four new chiral bis(amino alcohol)oxalamides (1-4: amino alcohol=leucinol, valinol, phenylglycinol, and phenylalaninol, respectively) have been prepared as low-molecular-weight organic gelators. Their gelation properties towards various organic solvents and mixtures were determined and these were then compared to related bis(amino acid) oxalamide gelators. Spectroscopic (FTIR, (1)H NMR) and X-ray diffraction

  作为低分子量有机胶凝剂，已经制备了四种新的手性双（氨基醇）草酰胺（1-4：氨基醇＝亮氨醇，缬氨醇，苯基甘醇和苯基丙氨醇）。确定了它们对各种有机溶剂和混合物的胶凝特性，然后将其与相关的双（氨基酸）草酰酰胺胶凝剂进行了比较。光谱（FTIR，（1）H NMR）和X射线衍射研究表明，亲脂性溶剂中（S，S）-1和消旋体1（rac-1）的主要组织基序涉及反双层的形成。（S，S）-1的X射线晶体结构也显示了这种双层结构。rac-2的晶体结构揭示了氢键键合聚集体的介观双层。在形成的双层中，胶凝剂分子通过草酰胺单元和OH基团之间的氢键连接而连接，而层间相互作用是通过亮氨酸的iBu基团之间的亲脂性相互作用实现的。草酸酰胺meso-1缺乏任何胶凝能力，只能单层结晶。rac-1在二氯甲烷中形成不稳定的凝胶；由于对称的介观双层的形成，这易于结晶。相反，rac-1在芳族溶剂中形成稳定的凝胶；相反，rac-1形成稳定的
• METHOD FOR PRODUCING OPTICALLY ACTIVE BISAMIDO ALCOHOL COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1698616A1

  公开（公告）日：2006-09-06

  It is provided that a method for producing an optically active bisamidoalcohol compound represented by the formula (3): wherein R1 represents a C1-6 alkyl group, an optionally substituted phenyl group, an optionally substituted aralkyl group or a hydrogen atom, or two R1s, which are bonded to the same carbon atom, are bonded to form a ring together with the carbon atom to which they are bonded, R2 represents a C1-6 alkyl group, an optionally substituted phenyl group, a 1-naphthyl group, a 2-naphthyl group or an optionally substituted aralkyl group, R3 and R4 are the same or different, and each represents a hydrogen atom or C1-3 alkyl group, m represents an integer of 0 to 2, and * represents an asymmetric center, which comprises reacting an optically active aminoalcohol compound represented by the formula (1): wherein R1, R2 and * are as defined above, with a diester compound represented by the formula (2): wherein R3, R4 and m are as defined above and R5 represents a C1-3 alkyl group, in the presence of a lithium compound.

  本发明提供了一种生产由式（3）代表的光学活性双氨基醇化合物的方法： 其中 R1 代表 C1-6 烷基、任选取代的苯基、任选取代的芳烷基或氢原子，或两个 R1 与同一碳原子键合，与其键合的碳原子一起形成环、 R2 代表 C1-6 烷基、任选取代的苯基、1-萘基、2-萘基或任选取代的芳基、 R3 和 R4 相同或不同，各自代表氢原子或 C1-3 烷基、 m 代表 0 至 2 的整数，以及 * 代表不对称中心，其中包括与由式（1）代表的光学活性氨基醇化合物反应： 其中 R1、R2 和 * 如上定义、 与式 (2) 所代表的二酯化合物反应： 其中 R3、R4 和 m 如上定义，R5 代表 C1-3 烷基、 在锂化合物存在下。
• New modulated design and synthesis of chiral CuII/SnIV bimetallic potential anticancer drug entity: In vitro DNA binding and pBR322 DNA cleavage activity
  作者：Sartaj Tabassum、Girish Chandra Sharma、Farukh Arjmand

  DOI：10.1016/j.saa.2012.01.020

  日期：2012.5

  A new chiral ligand scaffold L derived from (R)-2-amino-2-phenyl ethanol and diethyl oxalate was isolated and thoroughly characterized by various spectroscopic methods. The ligand L was allowed to react with CuCl2 center dot 2H(2)O and NiCl2 center dot 6H(2)O to achieve monometallic complexes 1 and 2, respectively. Subsequently modulation of 1 and 2 was carried out in the presence of SnCl4 center dot 5H(2)O to obtain heterobimetallic potential drug candidates 3 and 4 possessing (Cu-II/Sn-IV and Ni-II/Sn-IV) metallic cores, respectively and characterized by elemental analysis and spectroscopic data including H-1, C-13 and Sn-119 NMR in case of 3 and 4. In vitro DNA binding studies revealed that complex 3 avidly binds to DNA as quantified by K-b and K-sv values. Complex 3 exhibits a remarkable DNA cleavage activity (concentration dependent) with pBR322 DNA and the cleavage activity of 3 was significantly enhanced in the presence of activators and follows the order H2O2 > Asc > MPA > GSH. Complex 3 cleave pBR322 DNA via hydrolytic pathway and accessible to major groove of DNA. (C) 2012 Elsevier B.V. All rights reserved.
• Method for producing optically active bisamidoalcohol compound
  申请人：Itagaki Makoto

  公开号：US20070100163A1

  公开（公告）日：2007-05-03

  It is provided that a method for producing an optically active bisamidoalcohol compound represented by the formula (3): wherein R 1 represents a C1-6 alkyl group, an optionally substituted phenyl group, an optionally substituted aralkyl group or a hydrogen atom, or two R 1 s, which are bonded to the same carbon atom, are bonded to form a ring together with the carbon atom to which they are bonded, R 2 represents a C1-6 alkyl group, an optionally substituted phenyl group, a 1-naphthyl group, a 2-naphthyl group or an optionally substituted aralkyl group, R 3 and R 4 are the same or different, and each represents a hydrogen atom or C1-3 alkyl group, m represents an integer of 0 to 2, and * represents an asymmetric center, which comprises reacting an optically active aminoalcohol compound represented by the formula (1): wherein R 1 , R 2 and * are as defined above, with a diester compound represented by the formula (2): wherein R 3 , R 4 and m are as defined above and R 5 represents a C1-3 alkyl group, in the presence of a lithium compound.
• US7612236B2
  申请人：——

  公开号：US7612236B2

  公开（公告）日：2009-11-03