(1R)-2t-isopropyl-5c-methyl-cyclohexane-r-carboxylic acid amide | 27373-99-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-2t-isopropyl-5c-methyl-cyclohexane-r-carboxylic acid amide
• 英文别名: (1R)-2t-Isopropyl-5c-methyl-cyclohexan-r-carbonsaeure-amid；(1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide；3-p-Menthylcarbonsaeureamid；(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexane-1-carboxamide；(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide
• CAS: 27373-99-5
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: FINKDHKJINNQQW-KXUCPTDWSA-N

物化性质

• 熔点：
  145-146 °C
• 沸点：
  310.6±9.0 °C(Predicted)
• 密度：
  0.930±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-乙烯基吡啶 、 (1R)-2t-isopropyl-5c-methyl-cyclohexane-r-carboxylic acid amide 在 18-冠醚-6 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.0h， 生成 (1R,2S,5R)-2-isopropyl-5-methyl-N-(2-(pyridin-2-yl)ethyl)cyclohexanecarboxamide
  参考文献：
  名称：

  Amide Addition Reaction

  摘要：

  制备公式II化合物的方法包括将公式RCONH2化合物与公式IIIR化合物反应，其中公式IIIR是具有1至15个碳原子和可选地由氧、氮和硫独立选择的1至5个杂原子的基团，X和Y分别独立选择自H、甲基、乙基、OMe、OEt和它们的混合物组成的群；在溶剂中在碱的存在下进行反应。该方法可用于廉价制造某些具有商业价值的化合物，包括一些具有理想冷却性能的化合物。

  公开号：

  US20090030042A1
• 作为产物：
  描述：

  (1R,2S,5R)-2-异丙基-5-甲基环己烷羰基氯化物 在 ammonium hydroxide 作用下， 以 水 为溶剂， 生成 (1R)-2t-isopropyl-5c-methyl-cyclohexane-r-carboxylic acid amide
  参考文献：
  名称：

  [EN] SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS
  [FR] SYNTHÈSE DE DÉRIVÉS DE CYCLOHEXANE UTILES COMME AGENTS SENSORIELS DANS DES PRODUITS DE CONSOMMATION

  摘要：

  本发明提供了合成路径，用于制备基于环己烷的各种异构体冷却剂，例如薄荷酯和薄荷烷甲酰衍生物，特别是那些在酰胺氮上取代的，例如带有芳香环或芳基的。这些结构具有高冷却效能和持久的感官效果，使它们在各种消费品中有用。一种合成路径涉及使用铜催化剂将一种初级薄荷烷甲酰胺与芳香卤代烃偶联，这种反应在存在磷酸钾和水的情况下效果最佳。利用这种合成路径，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烷甲酰胺异构体以及具有在羧酰胺（C-1）位置上相反立体化学的新异构体，该新异构体意外地具有强效和持久的冷却效果。还提供了其他薄荷衍生物的新异构体的制备方案，这些衍生物包括酯类、醚类、羧酯类和其他N-取代羧酰胺，它们也可用作冷却剂。

  公开号：

  WO2010019730A1

文献信息

• PROCESS FOR MAKING NEO-ENRICHED p-MENTHANE COMPOUNDS
  申请人：Erman Mark B.

  公开号：US20120116113A1

  公开（公告）日：2012-05-10

  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.

  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。
• 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：Yelm Kenneth Edward

  公开号：US08426643B2

  公开（公告）日：2013-04-23

  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，例如酯类薄荷醇和薄荷烷基羧酰胺衍生物，特别是那些在酰胺氮上取代芳香环或芳基基团的衍生物。这些结构具有高冷却效力和持久的感官效果，使它们在各种消费品中有用。其中一种合成路线涉及使用铜催化剂将一种主要的薄荷烷基羧酰胺与芳香卤代烃偶联，这种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，包括具有与l-薄荷醇相同构型的薄荷烷基羧酰胺异构体和具有在羧酰胺（C-1）位置相反立体化学的新异构体，如新异构体意外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，这些异构体作为冷却剂是有用的，包括酯类、醚类、羧酸酯类和其他N-取代羧酰胺。
• 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。
• Smoking article
  申请人：BRITISH AMERICAN TOBACCO (INVESTMENTS) LIMITED

  公开号：US11528933B2

  公开（公告）日：2022-12-20

  In one aspect an aerosol-generating device comprising a smoking article and a heat source is described. The smoking article includes a smokable material and a cooling agent, the smokable material including a tobacco component. The heat source is disposed to heat, but not burn the smokable material in use. The cooling agent comprises a compound or a combination of compounds according to either of the following formulae, racemates, enantiomers and salts thereof (I, II).

  在一个方面，描述了一种气溶胶产生装置，它包括一个烟具和一个热源。烟具包括可吸食材料和冷却剂，可吸食材料包括烟草成分。热源的作用是在使用中加热但不燃烧可吸食材料。冷却剂包括符合以下任一式的化合物或化合物组合、外消旋体、对映体及其盐（I，II）。