diethyl 2-cyclohexylsuccinate | 75354-08-4

• 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: diethyl 2-cyclohexylsuccinate
• 英文别名: Diethyl 2-cyclohexylbutanedioate
• CAS: 75354-08-4
• 化学式: C₁₄H₂₄O₄
• 分子量: 256.342
• InChiKey: RQPNECGZAMRIRP-UHFFFAOYSA-N

物化性质

• 沸点：
  363 °C(Press: 3.8 Torr)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-cyclohexylsuccinate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到2-cyclohexyl-1,4-butanediol
  参考文献：
  名称：

  Synthesis and stereochemical assignment of geraniol- and nerol-derived Cygerol enantiomers

  摘要：

  The enantiomers (up to 99% ee) of both geraniol- and nerol-derived 2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid, the active ingredient of the wound healing medication Cygerol, were prepared via a low-temperature alkylation, basic hydrolysis, derivatization with (S)-4-benzyloxazolidin-2-one and chromatographic separation steps. The absolute configuration of stereocenters in the antipodes having an (E)- or (Z)-geometry of the internal double bond was determined based on characteristic H-1 NMR signals of the corresponding (S)-4-benzyloxazolidin-2-one-derived imides and on conversion to the known diethyl (S)-2-cyclohexylsuccinate and (S)-2-cyclohexylbutane-1,4-diol with reported specific rotations. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.10.024
• 作为产物：
  描述：

  ethyl (E)-2-cyclohexyl-5,9-dimethyldeca-4,8-dienoate 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 双氧水 、 氧气 、 臭氧 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.67h， 生成 diethyl 2-cyclohexylsuccinate
  参考文献：
  名称：

  Synthesis and stereochemical assignment of geraniol- and nerol-derived Cygerol enantiomers

  摘要：

  The enantiomers (up to 99% ee) of both geraniol- and nerol-derived 2-cyclohexyl-5,9-dimethyldeca-4,8-dienoic acid, the active ingredient of the wound healing medication Cygerol, were prepared via a low-temperature alkylation, basic hydrolysis, derivatization with (S)-4-benzyloxazolidin-2-one and chromatographic separation steps. The absolute configuration of stereocenters in the antipodes having an (E)- or (Z)-geometry of the internal double bond was determined based on characteristic H-1 NMR signals of the corresponding (S)-4-benzyloxazolidin-2-one-derived imides and on conversion to the known diethyl (S)-2-cyclohexylsuccinate and (S)-2-cyclohexylbutane-1,4-diol with reported specific rotations. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.10.024

文献信息

• Hydrogen Atom Transfer Reactions via Photoredox Catalyzed Chlorine Atom Generation
  作者：Samantha Rohe、Avery O. Morris、Terry McCallum、Louis Barriault

  DOI：10.1002/anie.201810187

  日期：2018.11.26

  waste‐limiting, and atom‐economical. The catalytic generation of chlorine atoms from chloride ions is one of the most challenging redox processes, where the requirement of harsh and oxidizing reaction conditions renders it seldom utilized in synthetic applications. We report the mild, controlled, and catalytic generation of chlorine atoms as a new opportunity for access to a wide variety of hydrogen atom transfer

  在实现氧化还原中性，废物限制和原子经济的有机转化中，化学惰性CH键的选择性官能化仍有待充分实现。由氯离子催化生成氯原子是最具挑战性的氧化还原过程之一，在苛刻和氧化反应条件下的需求使其很少用于合成应用。我们报告说，由于HCl的高稳定性，氯原子的温和，受控和催化生成是获得各种氢原子转移（HAT）反应的新机会。报道了在蓝光LED照射下，基于Ir的聚吡啶基络合物[Ir（dF（CF 3）ppy）2（dtbbpy）] Cl的光氧化还原介导的氯原子生成的发现。
• Redox-economical radical generation from organoborates and carboxylic acids by organic photoredox catalysis
  作者：Tatsuya Chinzei、Kazuki Miyazawa、Yusuke Yasu、Takashi Koike、Munetaka Akita

  DOI：10.1039/c5ra01826a

  日期：——

  A simple generation method of carbon radicals via 1e-oxidation of organotrifluoroborates and carboxylic acids by the action of an organophotoredox catalyst, 9-mesityl-10-methylacridinium perchlorate ([Acr+–Mes]ClO4), has been developed. This organophotocatalytic protocol is amenable to radical C–C bond formation with electron-deficient olefins.

  已经开发了一种简单的碳自由基生成方法，该方法是通过有机三氧化二硼催化剂9-间甲氧基-10-甲基ac鎓高氯酸盐（[Acr + -Mes] ClO 4）的作用对有机三氟硼酸酯和羧酸进行1e氧化。这种有机光催化方案适合与缺电子烯烃形成自由基C–C键。
• Photochemical Hydroacylation of Michael Acceptors Utilizing an Aldehyde as Photoinitiator
  作者：Ioanna K. Sideri、Errika Voutyritsa、Christoforos G. Kokotos

  DOI：10.1002/cssc.201901725

  日期：2019.9.20

  leading to good yields, and mechanistic experiments were performed to elucidate the catalyst's possible mechanistic pathway. Moreover, the inherent selectivity challenge regarding α,α-disubstituted aldehydes (decarbonylation problem) was studied and addressed.

  迈克尔受体的加氢酰化是形成新CC键的有用工具。在这项工作中，开发了一种环境友好的程序，利用4-氰基苯甲醛作为光引发剂，家用灯泡作为辐照源。各种各样的底物都具有良好的耐受性，从而导致了高收率，并且进行了机理实验以阐明催化剂的可能机理。此外，研究和解决了有关α，α-二取代醛的固有选择性挑战（脱羰问题）。
• Photocatalytic Giese‐Type Reaction with Alkylsilicates Bearing C,O‐Bidentate Ligands
  作者：Tatsuya Morofuji、Yu Matsui、Misa Ohno、Gun Ikarashi、Naokazu Kano

  DOI：10.1002/chem.202005300

  日期：2021.4.16

  photocatalytic Giese‐type reaction with alkylsilicates bearing C,O‐bidentate ligands as stable alkyl radical precursors has been reported. The alkylsilicates were prepared in one step from organometallic reagents. Not only primary, secondary, and tertiary alkyl radicals, but also elusive methyl radicals, could be generated by using the present reaction system. The generated radicals were trapped by electron‐deficient

  在本文中，已经报道了带有C，O-双齿配体的烷基硅酸盐作为稳定的烷基自由基前体的光催化Giese型反应。由有机金属试剂一步制备烷基硅酸盐。使用本反应系统不仅可以生成伯，仲和叔烷基，而且可以生成难以捉摸的甲基。生成的自由基被带有各种官能团的缺电子烯烃捕获，得到所需的烷基加合物。光反应后可以回收硅副产物。通过理论计算研究了自由基的生成过程，从而提供了从带有C，O-双齿配体的甲基硅酸盐轻松生成甲基自由基的见解。
• Green Photo-Organocatalytic C−H Activation of Aldehydes: Selective Hydroacylation of Electron-Deficient Alkenes
  作者：Giorgos N. Papadopoulos、Errika Voutyritsa、Nikolaos Kaplaneris、Christoforos G. Kokotos

  DOI：10.1002/chem.201705634

  日期：2018.2.1

  Selective C−H activation is an area of growing importance. Metal‐free C−H activation of branched aldehydes mediating the hydroacylation of electron‐deficient alkenes is an attractive transformation, but is limited by selectivity issues, especially in the case of α,α‐disubstituted aldehydes. Herein, we report a green, cheap, versatile, and easily reproducible selective hydroacylation of alkenes utilizing

  选择性CH活化是一个日益重要的领域。介导电子缺陷烯烃加氢酰化的支链醛的无金属CH活化是有吸引力的转变，但受选择性问题的限制，尤其是在α，α-二取代醛的情况下。本文中，我们报道了一种绿色，廉价，通用且易于重现的烯烃选择性加氢酰化反应，该方法利用苯乙醛酸作为光催化剂和普通家用灯泡进行辐照，从而获得了具有出色收率和选择性的产品。还研究了反应机理以说明高选择性。