N-ethoxycarbonylmethyl-(1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide | 1207722-14-2

• 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: N-ethoxycarbonylmethyl-(1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide
• 英文别名: N-Ethoxycarbonylmethyl-(1S,2S,5R)-2-isopropyl-5-methylcyclohexancarboxamide；ethyl 2-[[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexanecarbonyl]amino]acetate
• CAS: 1207722-14-2
• 化学式: C₁₅H₂₇NO₃
• 分子量: 269.384
• InChiKey: GWRCTWAPTXBPHW-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S,5R)-5-methyl-2-propan-2-ylcyclohexane-1-carbonyl chloride 、 甘氨酸乙酯盐酸盐 在 sodium carbonate 作用下， 以 正庚烷 、 水 为溶剂， 反应 4.5h， 生成 N-[(乙氧羰基)甲基]对薄荷基-3-甲酰胺 、 N-ethoxycarbonylmethyl-(1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide
  参考文献：
  名称：

  PROCESS FOR MAKING NEO-ENRICHED p-MENTHANE COMPOUNDS

  摘要：

  公开了一种制备富含新生代p-薄荷醛中间体的方法。Lewis酸催化的氧杂螺环化合物重排提供了一种包含正常(II)和新生代(III) p-薄荷醛的醛混合物：其中新生代醛(III)是主要产物。这种醛混合物容易被氧化成相应的羧酸，而这些酸则容易转化为大量的富含新生代p-薄荷酯或酰胺。这些酯和酰胺作为生理降温剂非常有价值。

  公开号：

  US20120116113A1

文献信息

• Process for making neo-enriched p-menthane compounds
  申请人：Renessenz LLC

  公开号：EP2450337A3

  公开（公告）日：2014-06-18

  A process for making neo-enriched p-menthane intermediates is disclosed. Lewis acid-catalyzed rearrangement of an oxaspiro compound provides an aldehyde mixture comprising normal (II) and neo (III) p-menthane-3-aldehydes: with the neo aldehyde (III) as the major product. The aldehyde mixture is readily oxidized to provide the corresponding carboxylic acids, and the acids are easily converted to a host of neo-enriched p-menthane esters or amides. The esters and amides are valuable as physiological coolants.

  揭示了一种制备富含新生代p-薄荷烷中间体的过程。Lewis酸催化的氧杂螺环化合物重新排列提供了包含正常（II）和新生代（III）p-薄荷烷-3-醛的醛混合物：其中新生代醛（III）为主要产物。该醛混合物容易氧化为相应的羧酸，并且这些酸易于转化为一系列富含新生代p-薄荷烷酯或酰胺。这些酯和酰胺作为生理制冷剂具有很高的价值。
• Physiological cooling compositions containing highly purified ethyl ester of N-[[5-methyl-2-(1-methylethyl)cyclohexyl] carbonyl]glycine
  申请人：Erman B. Mark

  公开号：US20050222256A1

  公开（公告）日：2005-10-06

  The present invention provides, in one aspect, a substantially pure ethyl ester of N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine. In another aspect, disclosed is a method for producing substantially pure ethyl ester of N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine. In still another aspect, disclosed are various consumer products comprising the substantially pure ethyl ester of N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine disclosed herein.

  本发明提供了一个方面，即N-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸的基本纯乙酯。另一个方面，揭示了一种制备基本纯乙酯N-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸的方法。还有另一个方面，揭示了包含本文所述基本纯乙酯N-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸的各种消费品。
• Synthesis of Cyclohexane Derivatives Useful as Sensates in Consumer Products
  申请人：Yelm Kenneth Edward

  公开号：US20100076080A1

  公开（公告）日：2010-03-25

  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基冷却剂的各种异构体的合成路线，例如酯类薄荷醇和酰胺衍生物，特别是那些在酰胺氮上被取代的，例如芳香环或芳基基团。这样的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。一种合成路线涉及一种铜催化的一次性薄荷醇酰胺与芳基卤化物的偶联反应，这种反应在存在磷酸钾和水的情况下效果最好。使用这种合成路线，可以制备特定的异构体，包括具有与l-薄荷醇相同构型的薄荷醇酰胺异构体和新的异构体，例如在羧酰胺（C-1）位置具有相反立体化学的新异构体。这种新异构体出人意料地具有强大而持久的冷却效果。还提供了其他薄荷醇衍生物的新异构体的制备方案，这些衍生物包括酯类、醚类、羧酸酯类和其他N-取代酰胺。
• 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。
• US7189760B2
  申请人：——

  公开号：US7189760B2

  公开（公告）日：2007-03-13