(R,R)-N-isopropyl-O,O-diacetyltartaric acid monoamide | 103688-30-8

• 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-isopropyl-O,O-diacetyltartaric acid monoamide
• 英文别名: (R,R)-N-isopropyldiacetyltartaric acid monoamide；(2R,3R)-2,3-diacetyloxy-4-oxo-4-(propan-2-ylamino)butanoic acid
• CAS: 103688-30-8
• 化学式: C₁₁H₁₇NO₇
• 分子量: 275.258
• InChiKey: GACMHHZUKFHDRY-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R,R)-N-isopropyl-O,O-diacetyltartaric acid monoamide 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 24.33h， 生成 Acetic acid (1R,2R)-2-acetoxy-1-(chrysen-2-ylcarbamoyl)-2-isopropylcarbamoyl-ethyl ester
  参考文献：
  名称：

  Novel 2-chrysenyl- and 1-pyrenyl-tartaramide derivatives as liquid chromatographic chiral phases for enantiomeric separation on porous graphitic carbon

  摘要：

  Four new chiral stationary phases have been obtained by coupling 2-chrysenylammine and l-pyrenylamine to chiral selector groups based on (R,R)-tartaric acid diamide, The compounds (R,R)-N-isopropyl-N'-(1-pyrenyl)tartaramide, (R,R)-N-(2-chrysenyl)-N'-isopropyltartaramide and (R,R)-N-(Z-chrysenyl)-N'-(3-nitrophenyl)tartaramide are strongly adsorbed on to porous graphitic carbon to produce a novel type of carbon-based chiral stationary phase. These new materials were evaluated by HPLC and were found to exhibit excellent enantioselectivity for various types of compound including aromatic alcohols, binaphthyl derivatives, beta-blocking agents and anti-inflammatory agents. These new chiral phases are very stable showing negligible tendency for phase loss or degradation. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00125-5
• 作为产物：
  描述：

  异丙胺 、 二-O-乙酰基-L-酒石酸酐 生成 (R,R)-N-isopropyl-O,O-diacetyltartaric acid monoamide
  参考文献：
  名称：

  New chiral polysiloxane derived from (R,R)-tartramide for enantiomer resolution by capillary gas chromatography

  摘要：

  The synthesis was conducted of a polysiloxane in which the (R,R)-tartramide derivative as a chiral selector was attached to the polysiloxane backbone via 11 methylene units. Capillary gas chromatography using this polysiloxane as a chiral stationary phase was found to be capable of recognizing the molecular chirality of broad categories of volatile enantiomers containing 1,2-diols, 1-methoxy-2-alkanols, dialkyl tartrates, methyloximes of 2-hydroxy ketones, N,N'-bis(perfluoroacyl)-1,2- and -1,3-diamines, N-alkylamides of 2- and 3-halo carboxylic acids, and N-alkylamides of 2- and 3-hydroxy carboxylic acids. The mode of complexation responsible for the observed enantioselection was ascribed to dual hydrogen bonding between the (R,R)-tartramide moiety of the polysiloxane and solute enantiomers to be resolved. Dual hydrogen bonding between (R,R)-tartramide and some enantiomers is discussed on the basis of the differences in H-1 NMR chemical shifts observed for the enantiomeric pair in a CDCl3 solution containing (R,R)-N,N'-diisopropyltartramide.

  DOI：

  10.1021/jo00010a024

文献信息

• A chiral stationary phase derived from (R,R)-tartramide with broadened scope of application to the liquid chromatographic resolution of enantiomers
  作者：Yasuo Dobashi、Shoji Hara

  DOI：10.1021/jo00388a026

  日期：1987.6
• Chiral polysiloxanes derived from (R,R)-tartramide for the gas chromatographic separation of enantiomers
  作者：Kouji. Nakamura、Shoji. Hara、Yasuo. Dobashi

  DOI：10.1021/ac00193a025

  日期：1989.9.15
• NAKAMURA, KOUJI;HARA, SHOJI;DOBASHI, YASUO, ANAL. CHEM., 61,(1989) N8, C. 2121-2124
  作者：NAKAMURA, KOUJI、HARA, SHOJI、DOBASHI, YASUO

  DOI：——

  日期：——
• DOBASHI, YASUO;NAKAMURA, KOUJI;SAEKI, TAKAFUMI;MATSUO, MASAAKI;HARA, SHOJ+, J. ORG. CHEM., 56,(1991) N0, C. 3299-3305
  作者：DOBASHI, YASUO、NAKAMURA, KOUJI、SAEKI, TAKAFUMI、MATSUO, MASAAKI、HARA, SHOJ+

  DOI：——

  日期：——
• DOBASHI YASUO; HARA SHOJI, J. ORG. CHEM., 52,(1987) N 12, 2490-2496
  作者：DOBASHI YASUO、 HARA SHOJI

  DOI：——

  日期：——