methyl 2-[[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexanecarbonyl]amino]acetate

• 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: methyl 2-[[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexanecarbonyl]amino]acetate
• 化学式: C₁₄H₂₅NO₃
• 分子量: 255.35
• InChiKey: ADDIXRGFGLEPLD-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

文献信息

• SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS
  申请人：The Procter & Gamble Company

  公开号：US20140186272A1

  公开（公告）日：2014-07-03

  The present invention provides synthetic routes for preparing various isomers of cyclohexane-based coolants, such as menthyl esters and menthanecarboxamide derivatives, in particular those substituted at the amide nitrogen, for example with an aromatic ring or aryl moiety. Such structures have high cooling potency and long lasting sensory effect, which make them useful in a wide variety of consumer products. One synthetic route involves a copper catalyzed coupling of a primary menthanecarboxamide with an aryl halide, such reaction working best in the presence of potassium phosphate and water. Using this synthetic route, specific isomers can be prepared including the menthanecarboxamide isomer having the same configuration as l-menthol and new isomers such as a neoisomer having opposite stereochemistry at the carboxamide (C-1) position. The neoisomer unexpectedly has potent and long lasting cooling effect. Preparation schemes for neoisomers of other menthyl derivatives which are useful as coolants, including esters, ethers, carboxy esters and other N-substituted carboxamides are also provided.

  本发明提供了合成环己烷基冷却剂的各种异构体的合成路线，例如酯类和酰胺衍生物，特别是在酰胺氮上取代芳香环或芳香基的衍生物。这些结构具有高冷却效能和持久的感官效应，使它们在各种消费品中有用。其中一种合成路线涉及将主要的酰胺基甲烷与芳香卤代物进行铜催化偶联反应，此反应在存在磷酸钾和水的情况下效果最佳。使用这种合成路线，可以制备特定的异构体，包括与l-薄荷醇具有相同构型的酰胺基甲烷异构体和具有相反立体化学的新异构体，例如在羧酰胺（C-1）位置。意外地，新异构体具有强烈和持久的冷却效果。还提供了其他薄荷醇衍生物的新异构体的制备方案，这些衍生物可用作冷却剂，包括酯类、醚类、羧酸酯类和其他N-取代酰胺类。