ethyl <(1R,4R)-bornylideneamino>acetate | 126452-07-1

• 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: ethyl <(1R,4R)-bornylideneamino>acetate
• 英文别名: ethyl 2-[[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanylidene]amino]acetate
• CAS: 126452-07-1
• 化学式: C₁₄H₂₃NO₂
• 分子量: 237.342
• InChiKey: XVXVSTHHSANECH-YGRLFVJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  巴豆酸甲酯 、 ethyl <(1R,4R)-bornylideneamino>acetate 生成 1-ethyl methyl (2R,3R)-2-methyl-N-<(1R,4R)-bornylidene>glutamate
  参考文献：
  名称：

  Highly diastereoselective Michael addition of lithiated camphor imines of glycine esters to .alpha.,.beta.-unsaturated esters. Synthesis of optically pure 5-oxo-2,4-pyrrolidinedicarboxylates of unnatural stereochemistry

  摘要：

  The lithium enolates of camphor imines of glycine esters underwent highly diastereoselective Michael additions to alpha,beta-unsaturated esters. The tightly chelated structure of the Z,E enolates and the selective approach of the alpha,beta-unsaturated esters to the re face of the enolates were responsible for the high diastereoselectivity observed. The use of alkylidenemalonate acceptors led to the diastereospecific formation of Michael adducts. Removal of the camphor auxiliary of the adducts and concomitant cyclization led to optically pure enantiomeric 5-oxo-2,4-pyrrolidinedicarboxylates of unnatural stereochemistry.

  DOI：

  10.1021/jo00008a052

文献信息

• Synthesis of 3,3-Dimethylglutamic Acid Derivatives as DPP-IV Inhibitors and Evaluation of Their Chemical Stability
  作者：Tsu Hsu、Ting-Yueh Tsai、Ya-Ju Tseng、Mei-Chun Chiou、Cheng-Tai Lu、Yu-Sheng Chao、Weir-Torn Jiaang

  DOI：10.1002/jccs.201190049

  日期：2011.2

  A novel five‐step synthesis of Boc‐3,3‐dimethylglutamic acid α‐ethyl ester 11 is reported. All the steps are high yielding and simple to carry out. By use of the 3,3‐dimethylglutamic acid building block, we successfully discovered a novel class of DPP‐IV inhibitors, Glu‐Pro‐Nitrile dipeptide mimics 2, with high potency (IC50 < 40 nM). The consequence of 3,3‐dimethyl substituent on the rate of intramolecular

  报道了Boc-3,3-二甲基谷氨酸α-乙酯11的新颖五步合成法。所有步骤均产率高且易于实施。通过使用3,3-二甲基谷氨酸构件，我们成功地发现了一类新型的DPP-IV抑制剂Glu-Pro-Nitrile二肽模拟物2，具有很高的效价（IC 50 <40 nM）。还评估了3,3-二甲基取代基对不同缓冲溶液中N末端胺和5位酰胺键之间分子内环化速率的影响。