2-(环己基甲基)-2-甲基丙二酸二乙酯 | 100597-39-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 2-(环己基甲基)-2-甲基丙二酸二乙酯
• 英文名称: diethyl 2-(cyclohexylmethyl)-2-methylmalonate
• 英文别名: cyclohexylmethyl-methyl-malonic acid diethyl ester；Cyclohexylmethyl-methyl-malonsaeure-diaethylester；Diethyl 2-(cyclohexylmethyl)-2-methylpropanedioate
• CAS: 100597-39-5
• 化学式: C₁₅H₂₆O₄
• mdl: MFCD25940866
• 分子量: 270.369
• InChiKey: LFIUTONCLXLZJX-UHFFFAOYSA-N

物化性质

• 沸点：
  326.1±15.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.866
• 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：

  2-(环己基甲基)-2-甲基丙二酸二乙酯 在 氢氧化钾 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 9.0h， 生成 beta-甲基-环己烷丙醇
  参考文献：
  名称：

  Kinetic resolution of primary 2-methyl-substituted alcohols via Pseudomonas cepacia lipase-catalysed enantioselective acylation

  摘要：

  研究了来自洋葱伯克霍尔德菌（Pseudomonas cepacia）的脂肪酶（如PFL、Amano PS等）在对一系列一级2-甲基取代醇使用乙酸乙烯酯作为酰基供体进行有机溶剂中的转酯化反应时的对映选择性。在对映选择性方面，最佳结果出现在3-芳基-2-甲基丙-1-醇中，大多数情况下对映体比例（E值）超过100，而其他3-取代的一级2-甲基丙-1-醇通常显示出较低的对映选择性：3-环烷基-2-甲基丙-1-醇（E ≈ 20）和2-甲基烷-1-醇（E ≈ 10）。将芳基团更靠近或远离手性中心会导致低对映选择性：2-芳基丙-1-醇（E < 10）、2-甲基-4-（2-噻吩基）丁-1-醇（E = 12）、2-甲基-5-（2-噻吩基）戊-1-醇（E = 3.2）和2-甲基-6-（2-噻吩基）己-1-醇（E = 3.8）。

  DOI：

  10.1039/a908023f
• 作为产物：
  描述：

  (碘甲基)环己烷 、 2-甲基丙二酸二乙酯钠盐 在 正丁醇 作用下， 生成 2-(环己基甲基)-2-甲基丙二酸二乙酯
  参考文献：
  名称：

  Barbituric Acids and Related Compounds Containing Alicyclicalkyl Groups¹

  摘要：

  DOI：

  10.1021/ja01196a040

文献信息

• Structure-based linker optimization of 6-(2-cyclohexyl-1-alkyl)-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3H)-ones as potent non-nucleoside HIV-1 reverse transcriptase inhibitors
  作者：Daxiong Li、Chunsheng Zhang、Wei Ding、Siming Huang、Le Yu、Nan Lu、Wenkai Pan、Yiming Li、Erik De Clercq、Christophe Pannecouque、Hongbing Zhang、Yueping Wang、Yanping He、Fener Chen

  DOI：10.1016/j.cclet.2020.09.035

  日期：2021.3

  our efforts toward the discovery of potent HIV-1 NNRTIs with diverse structures, a series of novel S-DACO analogues of 6-(2-cyclohexyl-1-alkyl)-2-(2-oxo-2-phenyl-ethylsulfanyl)pyrimidin-4(3H)-ones were designed, synthesized and evaluated for their antiviral activities in MT-4 cells. Most of these new compounds showed moderate to good activities against wild type HIV-1 with IC50 values ranging from 7.55 μmol/L

  为了继续努力发现具有不同结构的有效HIV-1 NNRTI，一系列新的6-（2-环己基-1-烷基）-2-（2-氧代-2-苯基-）的S -DACO类似物设计，合成并评价了乙硫基）嘧啶-4（3 H）-ones在MT-4细胞中的抗病毒活性。这些新化合物中的大多数对野生型HIV-1表现出中等至良好的活性，IC 50值在7.55μmol/ L至0.018μmol/ L范围内。其中，化合物5c被鉴定为最有希望的HIV-1复制抑制剂，IC 50  = 0.018μmol/ L，CC 50 = 194μmol/ L，SI = 12791，比参考药物NVP和DLV效力更强，可与AZT和EFV媲美。另外，与参考药物NVP / DLV和DB02相比，5c还表现出对双重突变HIV-1菌株RES056的改善的活性。初步的结构-活性关系（SAR）和分子模型研究也进行了讨论，这为指导新的S -DACO类似物的进一步合理设计提供了一些有用的指示。
• Overturning Established Chemoselectivities: Selective Reduction of Arenes over Malonates and Cyanoacetates by Photoactivated Organic Electron Donors
  作者：Eswararao Doni、Bhaskar Mondal、Steven O’Sullivan、Tell Tuttle、John A. Murphy

  DOI：10.1021/ja4050168

  日期：2013.7.31

  The prevalence of metal-based reducing reagents, including metals, metal complexes, and metal salts, has produced an empirical order of reactivity that governs our approach to chemical synthesis. However, this reactivity may be influenced by stabilization of transition states, intermediates, and products through substrate metal bonding. This article reports that in the absence of such stabilizing interactions, established chemoselectivities can be overthrown. Thus, photoactivation of the recently developed neutral organic superelectron donor 5 selectively reduces alkyl-substituted benzene rings in the presence of activated esters and nitriles, in direct contrast to metal-based reductions, opening a new perspective on reactivity. The altered outcomes arising from the organic electron donors are attributed to selective interactions between the neutral organic donors and the arene rings of the substrates.
• 2-Substituted histamines with G-protein-stimulatory activity
  作者：H Detert、A Hagelüken、R Seifert、W Schunack

  DOI：10.1016/0223-5234(96)88235-3

  日期：1995.1

  The cationic-amphiphilic 2-substituted histamines, 2-(3-chlorophenyl)histamine (2-[2-(3-chlorophenyl)-1H-imidazol-4-yl]ethanamine) and 2-(2-cyclohexylethyl)histamine, activate pertussis toxin-sensitive guanine nucleotide-binding proteins (G-proteins) of the G(i)-subfamily by a receptor-independent mechanism. We studied structure-activity relationships of 2-substituted histamine derivatives for this G-protein activation using six known and 12 newly synthesized compounds. Elongation of the alkyl chain between imidazole and the ring system enhanced the potency and efficiency of substances in activating high-affinity GTP hydrolysis, ie the enzymatic activity of G-protein alpha-subunits, in membranes of HL-60 leukemic cells. Cyclopentyl-, cyclohexyl- and norbornyl-substituted histamines were more effective and potent than phenyl-substituted histamines in mediating G-protein activation in HL-60 membranes and in activating reconstituted bovine brain G(i)/G(o)-proteins. Our data show that the chain length and the type of ring system are important determinants for receptor-independent G-protein activation by 2-substituted histamines. With respect to histamine H-1-receptors, most of the substances studied displayed weak antagonistic activity.
• Katznelson; Brodsky, Doklady Akademii Nauk SSSR, 1937, vol. 17, p. 477,479
  作者：Katznelson、Brodsky

  DOI：——

  日期：——