N,N'-Bis[(1R)-2-hydroxy-1-phenylethyl]-2,2-diethylmalonamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N,N'-Bis[(1R)-2-hydroxy-1-phenylethyl]-2,2-diethylmalonamide
• 英文别名: N¹,N³-bis((R)-2-hydroxy-1-phenylethyl)-2,2-diethylmalonamide；2,2-diethyl-N¹,N³-bis((R)-2-hydroxy-1-phenylethyl)malonamide；2,2-diethyl-N,N'-bis[(1R)-2-hydroxy-1-phenylethyl]propanediamide
• 化学式: C₂₃H₃₀N₂O₄
• 分子量: 398.502
• InChiKey: XALDKGYXONWYJG-PMACEKPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  N,N'-Bis[(1R)-2-hydroxy-1-phenylethyl]-2,2-diethylmalonamide 在 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 N-[(1R)-2-chloro-1-phenylethyl]-2-ethyl-2-[(4R)-4-phenyl-4,5-dihydrooxazol-2-yl]butyramide
  参考文献：
  名称：

  Reactivity of 2-methylene-1,3-dicarbonyl compounds: catalytic enantioselective Diels–Alder reaction

  摘要：

  The catalytic enantioselective Diets-Alder reaction of 1,1-dicarbonylethenes 3 with cyclopentadiene in the presence of Ti-TADDOLs, Mg-Ph-box and Mg-Ph-mox complexes was investigated. Although both exo- and enantioselectivity with Ti-TADDOL catalysts were poor, they were much improved using Mg-Ph-box or Mg-Ph-mox complexes as chiral catalysts. Thus, 3 was an efficient two-point binding dienophile and the non-C-2-syrrimetric Ph-mox 8 could be used as a chiral ligand. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00559-6
• 作为产物：
  描述：

  二乙基丙二酸二乙酯 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 5.0h， 生成 N,N'-Bis[(1R)-2-hydroxy-1-phenylethyl]-2,2-diethylmalonamide
  参考文献：
  名称：

  铜（II）催化的N-烯基脲的对映选择性分子内环化

  摘要：

  开发了第一个Cu（II）催化的N-烯基脲的高对映选择性分子内环化反应，用于手性邻位二氨基双环杂环的简洁组装。轻松去除氨基甲酸酯基团的羰基使得可以容易地获得对映体富集的环状邻位二胺。

  DOI：

  10.1021/acs.orglett.5b00131

文献信息

• Hydrogen bonding topology influences gelating properties of malonamides
  作者：Krešimir Molčanov、Tomislav Portada、Vesna Čaplar、Milan Jokić、Janja Makarević、Nataša Šijaković Vujičić、Zoran Štefanić、Mladen Žinić、Biserka Kojić-Prodić

  DOI：10.1007/s11224-012-0102-3

  日期：2013.4

  Preparation, structural characterisation and topology of hydrogen bonding networks of bis(phenylglycinol)malonamide, as well as its Cα mono- and dialkyl-substituted derivatives are described. Their hydrogen bonding motifs are described in view of their gelling properties. Topology of hydrogen bonding typical of malonamide gelators is compared with those of well-examined oxalamide gelators.

  介绍了双(苯基甘氨醇)丙二酰胺及其 Cα 单烷基和二烷基取代衍生物的制备、结构特征和氢键网络拓扑结构。从它们的胶凝特性角度描述了它们的氢键结构。并将丙二酰胺胶凝剂典型的氢键拓扑结构与经过充分研究的草酰胺胶凝剂的氢键拓扑结构进行了比较。
• Copper(II)-Catalyzed Enantioselective Intramolecular Cyclization of <i>N</i>-Alkenylureas
  作者：Shaomin Fu、Honghao Yang、Guoqiang Li、Yuanfu Deng、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/acs.orglett.5b00131

  日期：2015.2.20

  Cu(II)-catalyzed highly enantioselective intramolecular cyclization of N-alkenylureas was developed for the concise assembly of chiral vicinal diamino bicyclic heterocycles. Facile removal of carbonyl group of the carbamido moiety allowed for ready access to enantioenriched cyclic vicinal diamines.

  开发了第一个Cu（II）催化的N-烯基脲的高对映选择性分子内环化反应，用于手性邻位二氨基双环杂环的简洁组装。轻松去除氨基甲酸酯基团的羰基使得可以容易地获得对映体富集的环状邻位二胺。
• Reactivity of 2-methylene-1,3-dicarbonyl compounds: catalytic enantioselective Diels–Alder reaction
  作者：Masashige Yamauchi、Takashi Aoki、Ming-Zhu Li、Yuko Honda

  DOI：10.1016/s0957-4166(01)00559-6

  日期：2001.12

  The catalytic enantioselective Diets-Alder reaction of 1,1-dicarbonylethenes 3 with cyclopentadiene in the presence of Ti-TADDOLs, Mg-Ph-box and Mg-Ph-mox complexes was investigated. Although both exo- and enantioselectivity with Ti-TADDOL catalysts were poor, they were much improved using Mg-Ph-box or Mg-Ph-mox complexes as chiral catalysts. Thus, 3 was an efficient two-point binding dienophile and the non-C-2-syrrimetric Ph-mox 8 could be used as a chiral ligand. (C) 2002 Elsevier Science Ltd. All rights reserved.