2-fluoro-4-methyl-1-(1-methylethyl)cyclohexane | 53731-15-0

• 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: 2-fluoro-4-methyl-1-(1-methylethyl)cyclohexane
• 英文别名: 1-fluoro-2-isopropyl-5-methylcyclohexane；menthyl fluoride；1-Fluor-2-isopropyl-5-methyl-cyclohexan；2-Fluoro-4-methyl-1-(propan-2-yl)cyclohexane；2-fluoro-4-methyl-1-propan-2-ylcyclohexane
• CAS: 53731-15-0
• 化学式: C₁₀H₁₉F
• 分子量: 158.259
• InChiKey: QFWBGMBGALACAU-UHFFFAOYSA-N

物化性质

• 沸点：
  176.7±9.0 °C(Predicted)
• 密度：
  0.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2903890090

反应信息

• 作为反应物：
  描述：

  2-fluoro-4-methyl-1-(1-methylethyl)cyclohexane 在 Sm(HMDS)₂ 作用下， 以 正己烷 为溶剂， 反应 0.67h， 以90%的产率得到Menthane
  参考文献：
  名称：

  Solvent dependent reductive defluorination of aliphatic C–F bonds employing Sm(HMDS)2

  摘要：

  在正己烷中，Sm(HMDS)2能高效地催化一级、二级和三级烷基氟化物的快速断裂，产率良好至极佳。与使用四氢呋喃作为溶剂相比，Sm(HMDS)2在正己烷中对C-F键的还原能力表现出独特的增强效果。

  DOI：

  10.1039/c3cc37828d
• 作为产物：
  描述：

  薄荷脑 在 [双(2-甲氧基乙基)胺]三氟化硫 作用下， 反应 16.0h， 生成 2-fluoro-4-methyl-1-(1-methylethyl)cyclohexane
  参考文献：
  名称：

  1 H-19F二维NMR标量偶合相关脉冲序列的比较。

  摘要：

  在单氟化和多氟化测试化合物上，评估了通过标量偶合检测异质COSY，HETCOR，HMQC和HSQC二维NMR脉冲序列检测（19）F-（1）H相关性的有效性。这些序列的所有四个都有效地观察（1）H-（19）的F的相关性，即使用（19）F或（1）H作为观测核。所有四个序列都可以在一定程度上进行调节以优先观察更大或更小的偶联。A 1 / 2J回波过滤器有效地应用于删除（2）JFF强耦合的伪像。该HETCOR实验提供灵敏度，分辨率和选择性建华最佳的整体组合。

  DOI：

  10.1002/mrc.4052

文献信息

• Process for producing fluoro-compounds
  申请人：Kondo Norihisa

  公开号：US20090030228A1

  公开（公告）日：2009-01-29

  The present invention provides a process for producing highly pure fluoro-compounds by making use of less costly and readily handleable N-(2-chloro-1,1,2-trifluoroethyl)diethylamine. The process produces little or no chlorinated by-products. Specifically the present invention provides a process for producing a fluoro-compound, comprising fluorinating an alcohol derivative represented by the following general formula (1): R 1 R 2 R 3 COH  (1) (wherein R 1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, aryl group, alkylcarbonyl group, alkoxycarbonyl group, arylcarbonyl group or aryloxycarbonyl group; and R 2 and R 3 are each independently a substituted or unsubstituted alkyl group, aryl group, alkylcarbonyl group, alkoxycarbonyl group, arylcarbonyl group or aryloxycarbonyl group, wherein at least two of R 1 , R 2 and R 3 may together form part of a ring structure, either with or without a heteroatom) with N,N-diethyl-2-chloro-1,1,2-trifluoroethylamine to form a fluoro-compound represented by the following general formula (2): R 1 R 2 R 3 CF  (2) (wherein R 1 , R 2 and R 3 are as defined above), the process being characterized in that an alcohol derivative represented by the following general formula (3): R 4 OH  (3) (wherein R 4 represents a substituted or unsubstituted alkyl group or aryl group) is added to the reaction system.

  本发明提供了一种利用成本较低且易于处理的N-(2-氯-1,1,2-三氟乙基)二乙胺生产高纯度氟化合物的方法。该方法几乎不产生氯化副产物。具体而言，本发明提供了一种生产氟化合物的方法，包括将由下述通式(1)表示的醇衍生物进行氟化：R1R2R3COH (其中R1代表氢原子、取代或未取代的烷基、芳基、烷基羰基、烷氧羰基、芳基羰基或芳氧羰基；R2和R3分别独立地代表取代或未取代的烷基、芳基、烷基羰基、烷氧羰基、芳基羰基或芳氧羰基，其中R1、R2和R3中的至少两个可以共同形成环结构，带有或不带有杂原子)与N,N-二乙基-2-氯-1,1,2-三氟乙基胺反应，形成由下述通式(2)表示的氟化合物：R1R2R3CF (其中R1、R2和R3如上所定义)，其特征在于向反应体系中加入由下述通式(3)表示的醇衍生物：R4OH (其中R4代表取代或未取代的烷基或芳基)。
• Light‐Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single‐Electron Oxidation with TEDA ^2+.
  作者：Francisco José Aguilar Troyano、Frederic Ballaschk、Marcel Jaschinski、Yasemin Özkaya、Adrián Gómez‐Suárez

  DOI：10.1002/chem.201903702

  日期：2019.11.7

  The synthesis of tertiary alkyl fluorides through a formal radical deoxyfluorination process is described herein. This light-mediated, catalyst-free methodology is fast and broadly applicable allowing for the preparation of C-F bonds from (hetero)benzylic, propargylic, and non-activated tertiary alcohol derivatives. Preliminary mechanistic studies support that the key step of the reaction is the single-electron

  本文描述了通过正式的自由基脱氧氟化方法合成叔烷基氟。这种无光催化，无催化剂的方法是快速且广泛适用的，可用于从（杂）苄基，炔丙基和未活化的叔醇衍生物制备CF键。初步的机理研究支持该反应的关键步骤是草酸铯的单电子氧化（可从相应的叔醇中轻松获得）与原位生成的TEDA2 +。（TEDA：N-（氯甲基）三亚乙基二胺），一种衍生自Selectfluor®的自由基阳离子。
• PROCESS FOR PRODUCTION OF FLUOROCOMPOUNDS
  申请人：Tosoh F-Tech, Inc.

  公开号：EP1903021A1

  公开（公告）日：2008-03-26

  The present invention provides a process for producing highly pure fluoro-compounds by making use of less costly and readily handleable N-(2-chloro-1,1,2-trifluoroethyl)diethylamine. The process produces little or no chlorinated by-products. Specifically the present invention provides a process for producing a fluoro-compound, comprising fluorinating an alcohol derivative represented by the following general formula (1):         R1R2R3COH     (1) (wherein R1 represents a hydrogen atom, a substituted or unsubstituted alkyl group, aryl group, alkylcarbonyl group, alkoxycarbonyl group, arylcarbonyl group or aryloxycarbonyl group; and R2 and R3 are each independently a substituted or unsubstituted alkyl group, aryl group, alkylcarbonyl group, alkoxycarbonyl group, arylcarbonyl group or aryloxycarbonyl group, wherein at least two of R1, R2 and R3 may together form part of a ring structure, either with or without a heteroatom) with N,N-diethyl-2-chloro-1,1,2-trifluoroethylamine to form a fluoro-compound represented by the following general formula (2):         R1R2R3CF     (2) (wherein R1, R2 and R3 are as defined above), the process being characterized in that an alcohol derivative represented by the following general formula (3):         R4OH     (3) (wherein R4 represents a substituted or unsubstituted alkyl group or aryl group) is added to the reaction system.

  本发明提供了一种利用成本较低、易于处理的 N-(2-氯-1,1,2-三氟乙基)二乙胺生产高纯度氟化合物的工艺。该工艺几乎不会产生氯化副产品。 具体地说，本发明提供了一种生产氟化合物的工艺，包括对由下式通式（1）代表的醇衍生物进行氟化处理： R1R2R3COH (1) (其中 R1 代表氢原子、取代或未取代的烷基、芳基、烷基羰基、烷氧羰基、芳基羰基或芳氧羰基；和 R2 和 R3 各自独立地为取代或未取代的烷基、芳基、烷基羰基、烷氧羰基、芳基羰基或芳氧羰基，其中 R1、R2 和 R3 中至少有两个可共同构成环结构的一部分，可带或不带杂原子）与 N，N-二乙基-2-氯-1，1，2-三氟乙胺形成下通式（2）所代表的氟化合物： R1R2R3CF (2) (其中 R1、R2 和 R3 如上定义)，该工艺的特征在于由下式通式(3)代表的醇衍生物： R4OH (3) (其中 R4 代表取代或未取代的烷基或芳基）加入反应体系中。
• Practical and General Method for Direct Synthesis of Alkyl Fluorides from Alcohols under Mild Conditions
  作者：Babasaheb P. Bandgar、Vinod T. Kamble、Ankush V. Biradar

  DOI：10.1007/s00706-005-0296-9

  日期：2005.9

  A variety of alcohols were treated with Ph3P and KF in CCl4-DMF at room temperature to afford the corresponding fluorides in very good yields.
• Bis(2-methoxyethyl)aminosulfur Trifluoride:  A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability
  作者：Gauri S. Lal、Guido P. Pez、Reno J. Pesaresi、Frank M. Prozonic、Hansong Cheng

  DOI：10.1021/jo990566+

  日期：1999.9.1

  Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)(2)NSF3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C2H5)(2)NSF3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.