ethyl 2-(cyclohexylmethyl)acrylate | 92822-55-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-(cyclohexylmethyl)acrylate
• 英文别名: ethyl 2-(cyclohexylmethyl)prop-2-enoate
• CAS: 92822-55-4
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: QUXUHAHHKMINNY-UHFFFAOYSA-N

物化性质

• 沸点：
  80 °C(Press: 4 Torr)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-(cyclohexylmethyl)acrylate 在 氢氧化钾 作用下， 以 乙醇 、 苯 为溶剂， 反应 3.5h， 生成 2-(Acetylsulfanylmethyl)-3-cyclohexylpropanoic acid
  参考文献：
  名称：

  New orally active enkephalinase inhibitors: their synthesis, biological activity, and analgesic properties

  摘要：

  A series of (4S)-4-[(2S)-benzyl-3-mercaptopropionylamino]-4-(N-phenylcarbamoyl)-butyric acids has been identified as potent systemically active enkephalinase inhibitors. Structure-activity relationships (SAR) are discussed. Further chemical modification of the inhibitors was carried out in order to identify the inhibitors which are orally active in an animal model. Compounds of particular interest are the prodrug-like analogues, including 5b (ONO-9902). Their analgesic effects after oral administration were evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10048-7
• 作为产物：
  描述：

  2-溴甲基丙烯酸乙酯 在 偶氮二异丁腈 作用下， 反应 26.0h， 生成 ethyl 2-(cyclohexylmethyl)acrylate
  参考文献：
  名称：

  Use of allylic triflones for allylation of C-H bonds

  摘要：

  Allylic triflones react with THF and cyclohexane and related molecules to undergo a trifluoromethyl radical mediated C-H functionalization reaction. Due to polar effects, the reactions benefit from the presence of electron-withdrawing group at the 2-position of the allylic triflones. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00775-8

文献信息

• Preparation of Alkylmagnesium Reagents from Alkenes through Hydroboration and Boron-Magnesium Exchange
  作者：Markus A. Reichle、Bernhard Breit

  DOI：10.1002/anie.201201704

  日期：2012.6.4

  Tolerant: Alkylmagnesium reagents can be synthesized from alkenes through a sequence of hydroboration and subsequent boron–magnesium exchange using a method that tolerates different functional groups (see scheme). The resulting alkylmagnesium reagents can be used in carbon–carbon bond forming reactions, such as alkylation reactions or transition‐metal‐catalyzed cross‐coupling reactions.

  宽容：烷基镁试剂可从烯烃通过硼氢化反应和随后的硼镁交换的序列使用容忍不同的官能团的方法（参见方案）来合成。所得的烷基镁试剂可用于碳-碳键形成反应，例如烷基化反应或过渡金属催化的交叉偶联反应。
• Esters α-méthyléniques par substitution d'éthers et d'acétates dérivés de l'α-(hydroxyméthyl)acrylate d'éthyle
  作者：Hassen Amri、Monique Rambaud、Jean Villiéras

  DOI：10.1016/0022-328x(90)87047-h

  日期：1990.2

  α-(Methylene)alkanoic esters are prepared in high yields by substitution of α-(acetoxymethyl)acrylates using Grignard reagents in the presence of a catalytic amount of copper(I) salt. This reaction can be applied to lithium enolates of esters and ketones and to give functional α-(methylene) alkanoic esters, products of great interest for the synthesis of active biological compounds (sarkomycin, α-(methylene)

  通过在催化量的铜（I）盐存在下使用格氏试剂替换α-（乙酰氧基甲基）丙烯酸酯，可以高产率制备α-（亚甲基）链烷酸酯。该反应可用于酯和酮的烯醇锂，并得到功能性α-（亚甲基）链烷酸酯，这对于合成活性生物化合物（沙克霉素，α-（亚甲基）δ-戊内酯）具有重要意义。
• 2-Functionalized allyl tris(trimethylsilyl)silanes as radical-based allylating agents
  作者：Chryssostomos Chatgilialoglu、Carla Ferreri、Marco Ballestri、Dennis P. Curran

  DOI：10.1016/0040-4039(96)01354-8

  日期：1996.8

  Radical allylations with 2-functionalized allyl tris(trimethylsilyl)silanes occur under mild conditions in good to excellent yield provided that the radical precursor and the silane have the appropriate electronic pairing. These reactions offer tin-free altermatives for transformations that are currently conducted with allyl stannanes.

  如果自由基前体和硅烷具有适当的电子配对，则在温和的条件下，以2官能化的烯丙基三（三甲基甲硅烷基）硅烷进行自由基烯丙基化反应会产生良好或极好的收率。这些反应为目前用烯丙基锡烷进行的转化提供了无锡替代品。
• Trifluoromethyl-Radical-Mediated Carbonylation of Alkanes Leading to Ethynyl Ketones
  作者：Yoshitaka Uenoyama、Takahide Fukuyama、Keisuke Morimoto、Osamu Nobuta、Hidefumi Nagai、Ilhyong Ryu

  DOI：10.1002/hlca.200690228

  日期：2006.10

  The carbonylation of alkanes 1 under radical-reaction conditions was examined by using ethynyl triflone A as the unimolecular chain-transfer (UMCT) reagent. Good to moderate yields of ethynyl ketones 2 were prepared by means of this three-component coupling reaction. Higher CO pressures as well as lower concentrations of triflone A improved the efficiency of the reaction over the direct addition, the

  使用乙炔基三氟甲酮A作为单分子链转移（UMCT）试剂，检查了自由基反应条件下烷烃1的羰基化作用。通过这种三组分偶联反应，制备了乙炔基酮2的良好至中等的产率。与直接添加相比，较高的CO压力和较低的三氟甲酮A浓度提高了反应效率，后者导致烷基化乙炔3。与与A的反应相反，环己烷（1a）与烯丙基三酮B的反应。（＝ 2-亚甲基-3-[[（三氟甲基）磺酰基]丙酸乙酯）在CO存在下得到羰基化产物的混合物，包括由环己烷，CO和烯丙基三氟乙烯乙的两个分子各自形成的8a。
• Organic photoredox catalysis for the oxidation of silicates: applications in radical synthesis and dual catalysis
  作者：Christophe Lévêque、Ludwig Chenneberg、Vincent Corcé、Cyril Ollivier、Louis Fensterbank

  DOI：10.1039/c6cc04636c

  日期：——

  Metal free photooxidation of alkyl bis(catecholato)silicates with the organic dye, 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyano-benzene (4CzIPN), allows the smooth formation of alkyl radicals. The latter can be efficiently engaged either with radical acceptors to...

  有机染料1,2,3,5-四（咔唑-9-基）-4,6-二氰基苯（4CzIPN）的烷基双（邻苯二酚）硅酸盐的无金属光氧化作用可平滑地形成烷基。后者可以有效地与激进受体结合以...