2-异丙基-5-甲基环己烷甲腈 | 54556-12-6

• 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
• 中文名称: 2-异丙基-5-甲基环己烷甲腈
• 英文名称: 2-isopropyl-5-methyl-cyclohexanecarbonitrile
• 英文别名: 3-Cyan-p-menthan；2-Isopropyl-5-methyl-cyclohexancarbonitril；5-Methyl-2-(propan-2-yl)cyclohexane-1-carbonitrile；5-methyl-2-propan-2-ylcyclohexane-1-carbonitrile
• CAS: 54556-12-6
• 化学式: C₁₁H₁₉N
• 分子量: 165.279
• InChiKey: AWVUYKHSNNYPOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-异丙基-5-甲基环己烷甲腈 在 氢氧化钾 作用下， 生成 2-异丙基-5-甲基环己烷甲酸
  参考文献：
  名称：

  Lueck, Apotheker Zeitung, vol. 36, p. 279

  摘要：

  DOI：
• 作为产物：
  描述：

  1-氯-2-异丙基-5-甲基环己烷 、 氰化钾 生成 2-异丙基-5-甲基环己烷甲腈
  参考文献：
  名称：

  Lueck, Apotheker Zeitung, vol. 36, p. 279

  摘要：

  DOI：

文献信息

• [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。
• 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。
• Method for making amides
  申请人：——

  公开号：US20020028969A1

  公开（公告）日：2002-03-07

  The invention relates to the manufacture of amide compounds provided through the reaction of nitrile compounds and a sulfate compound to form the related amide compound. In a preferred embodiment a diol or a triol is employed as a solvent, thereby increasing the yield of the product.

  本发明涉及通过将腈化合物和硫酸盐化合物反应形成相关酰胺化合物的制备方法。在首选实施例中，使用二元醇或三元醇作为溶剂，从而增加产物的收率。
• Process for obtaining N-monosubstituted amides
  申请人：Millennium Specialty Chemicals, Inc.

  公开号：US20030120113A1

  公开（公告）日：2003-06-26

  A process for obtaining an amide of the general formula R-(CO)—NH—CH 2 —X involves contacting a nitrile of the general formula R-CN with: a) an acid; and c) an alkoxy-containing compound comprising at least one alkoxy functionality of the general formula —OCH 2 -X; wherein R is hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, which substituents can be substituted or unsubstituted; wherein X is hydrogen or a radical having the general formula —CHR 1 R 2 ; and wherein R 1 and R 2 independently or collectively represent hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, or any combination thereof, which substituents can be substituted or unsubstituted. Moreover, the inventive process can involve other similar reactions, for example, at least one nitrile can be reacted with a reagent comprising both (i) at least one suitable alkoxy functionality; and (ii) at least one suitable acid functionality.

  一种获得通式为 R-(CO)-NH-CH的酰胺的工艺 2 -X的酰胺的工艺包括将通式为R-CN的腈与以下物质接触： a) 酸；和 c) 含有至少一个通式 -OCH 的烷氧基官能团的烷氧基化合物 2 -X; 其中 R 是氢或烷基、环烷基、烯基、环烯基、炔基、芳基或杂环取代基，这些取代基可以是取代或未取代的；其中 X 是氢或通式为 -CHR 的基团 1 R 2 其中 R 1 和 R 2 独立或共同代表氢或烷基、环烷基、烯基、环烯基、炔基、芳基或杂环基取代基，或它们的任意组合，这些取代基可以是取代的或未取代的。此外，本发明工艺还可以涉及其他类似的反应，例如，至少一个腈可以与同时包含(i)至少一个合适的烷氧基官能团；和(ii)至少一个合适的酸官能团的试剂反应。