N-[4-(cyanomethyl)phenyl]-(1R,2S,SR)-2-isopropyl-5-methylcyclohexanecarboxamide | 1187627-98-0

• 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: N-[4-(cyanomethyl)phenyl]-(1R,2S,SR)-2-isopropyl-5-methylcyclohexanecarboxamide
• 英文别名: (1R,2S,5R)-N-[4-(cyanomethyl)phenyl]-5-methyl-2-(1-methylethyl)cyclohexane-1-carboxamide；N-p-phenylacetonitrile menthylcarboxamide；N-para-benzene acetonitrile menthane；FEMA 4496；N-[4-(cyanomethyl)phenyl]-(1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide；N-p-Benzeneacetonitrile menthanecarboxamide；(1R,2S,5R)-N-[4-(cyanomethyl)phenyl]-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide
• CAS: 1187627-98-0
• 化学式: C₁₉H₂₆N₂O
• 分子量: 298.428
• InChiKey: FPJRGEOLQICYQZ-FHLIZLRMSA-N

物化性质

• 沸点：
  491.5±28.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)
• 物理描述：
  Solid white powder; Refreshing cool aroma
• 溶解度：
  Practically insoluble or insoluble in water

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[4-(cyanomethyl)phenyl]-(1R,2S,SR)-2-isopropyl-5-methylcyclohexanecarboxamide 、 (1S,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxamide 、 4-碘苯基乙腈, 在 ethyl acetate n-hexane 作用下， 生成 N-p-phenylacetonitrile neomenthylcarboxamide
  参考文献：
  名称：

  Synthesis of cyclohexane derivatives useful as sensates in consumer products

  摘要：

  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。

  公开号：

  US08426643B2
• 作为产物：
  描述：

  (-)-menthyl chloride 在 氯化亚砜 、 magnesium 作用下， 以 甲苯 为溶剂， 反应 18.5h， 生成 N-[4-(cyanomethyl)phenyl]-(1R,2S,SR)-2-isopropyl-5-methylcyclohexanecarboxamide
  参考文献：
  名称：

  N-对苯乙腈基薄荷烷基甲酰胺及N-对苯乙腈基新薄荷烷基甲酰胺的制备方法

  摘要：

  本发明公开了一种N‑对苯乙腈基薄荷烷基甲酰胺及N‑对苯乙腈基新薄荷烷基甲酰胺的制备方法，本发明采用L‑氯代薄荷烷制备格氏试剂，然后与二氧化碳加成、酸化一锅法制备薄荷基甲酸及新薄荷基甲酸，然后分离薄荷基甲酸及新薄荷基甲酸得到单体，之后薄荷基甲酸、新薄荷基甲酸分别与氯化亚砜反应，再分别与对氨基苯乙腈反应制备N‑对苯乙腈基薄荷烷基甲酰胺及N‑对苯乙腈基新薄荷烷基甲酰胺。

  公开号：

  CN117466772A

文献信息

• METHYL MENTHOL DERIVATIVE AND COOLING AGENT COMPOSITION CONTAINING SAME
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20180057447A1

  公开（公告）日：2018-03-01

  The purpose of the present invention is to provide a cooling agent composition containing a novel methyl menthol derivative having no undesirable feeling of stimulation, malodor, bitterness, or the like, it being possible to use the cooling agent composition as a cooling agent or sensory stimulation agent having exceptional persistence of a sense of coolness and refreshing feeling. The present invention pertains to a cooling agent composition containing a methyl menthol derivative represented by general formula (1A) or general formula (1B).

  本发明的目的是提供一种冷却剂组合物，其中包含一种新型的甲基薄荷醇衍生物，不具有刺激感、恶臭、苦味等不良感觉，可以将该冷却剂组合物用作具有出色持久感觉的凉爽和清新感的冷却剂或感官刺激剂。本发明涉及一种含有由通式（1A）或通式（1B）表示的甲基薄荷醇衍生物的冷却剂组合物。
• Compositions With A Cooling Effect
  申请人：The Procter & Gamble Company

  公开号：US20190330141A1

  公开（公告）日：2019-10-31

  Personal care compositions, such as oral care and skin care compositions comprising one or more coolants. The pleasant cool sensation provided by a coolant is enhanced in terms of quicker onset, greater intensity, impact or longer duration, which improves appeal and acceptability of the compositions to consumers. Also, a treatment for excess adipose tissue by applying an activating compound directly to a targeted area.

  个人护理组合物，如口腔护理和皮肤护理组合物，包括一个或多个冷却剂。冷却剂提供的愉悦冷感在更快的开始、更大的强度、影响或更长的持续时间方面得到增强，这提高了组合物对消费者的吸引力和可接受性。此外，通过将活化化合物直接应用于靶向区域来治疗多余的脂肪组织。
• 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。
• [EN] SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS<br/>[FR] SYNTHÈSE DE DÉRIVÉS DE CYCLOHEXANE UTILES COMME AGENTS SENSORIELS DANS DES PRODUITS DE CONSOMMATION
  申请人：PROCTER & GAMBLE

  公开号：WO2010019730A1

  公开（公告）日：2010-02-18

  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。
• 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。