4-氧代十二烷酸乙酯 | 59941-35-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 中文名称: 4-氧代十二烷酸乙酯
• 英文名称: ethyl 4-oxododecanoate
• 英文别名: 4-Oxododecansaeure-ethylester；Dodecanoic acid, 4-oxo-, ethyl ester
• CAS: 59941-35-4
• 化学式: C₁₄H₂₆O₃
• 分子量: 242.359
• InChiKey: GSECHIHYKBKSOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氧代十二烷酸乙酯 在 lithium aluminium tetrahydride 、 sodium hexamethyldisilazane 、 pyridinium chlorochromate 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 顺式-12-十九碳烯-9-酮
  参考文献：
  名称：

  Sorochinskaya, A. M.; Kovalev, B. G.; Avdeeva, L. A., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 2, p. 277 - 283

  摘要：

  DOI：
• 作为产物：
  描述：

  (±)-二氢-5-辛基-2(3H)-呋喃酮 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 4-氧代十二烷酸乙酯
  参考文献：
  名称：

  Synthesis of Pseudomonas quorum-sensing autoinducer analogs and structural entities required for induction of apoptosis in macrophages

  摘要：

  The synthesis of the analogs of N-3-oxododecanoyl-L-homoserine lactone (1) and their structure-activity relationship for the apoptotic induction in macrophages, P388D1 cells, are described. It was revealed that the position of the oxo group in the acyl side chain in addition to the presence of the L-homoserine lactone unit is crucial for the apoptosis-inducing activity. Furthermore, the long acyl side chains with hydrophobic distal ends are preferable for the activity. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.054

文献信息

• Synthesis of Functionalized Dialkyl Ketones from Carboxylic Acid Derivatives and Alkyl Halides
  作者：Alexander C. Wotal、Daniel J. Weix

  DOI：10.1021/ol300217x

  日期：2012.3.16

  Unsymmetrical dialkyl ketones can be directly prepared by the nickel-catalyzed reductive coupling of carboxylic acid chlorides or (2-pyridyl)thioesters with alkyl iodides or benzylic chlorides. A wide variety of functional groups are tolerated by this process, including common nitrogen protecting groups and C–B bonds. Even hindered ketones flanked by tertiary and secondary centers can be formed. The

  不对称二烷基酮可以通过羧酸氯化物或（2-吡啶基）硫酯与烷基碘或苄基氯化物的镍催化还原偶联直接制备。这个过程可以容忍各种各样的官能团，包括常见的氮保护基团和 C-B 键。甚至可以形成侧接有三级和二级中心的受阻酮。提出的机制涉及(L)Ni(烷基) 2中间体与羧酸衍生物的反应。
• Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids
  作者：Yanhui Lu、Hidefumi Nakatsuji、Yukimasa Okumura、Lu Yao、Kazuaki Ishihara

  DOI：10.1021/jacs.8b02607

  日期：2018.5.16

  Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to α-Tocopherol

  2-烯基苯酚和烯酰胺的催化对映选择性卤环化已经通过使用手性酰胺磷酸盐催化剂和卤代路易斯酸实现。密度泛函理论计算表明催化剂的路易斯碱度在反应性和对映选择性中起重要作用。所得手性卤代色满可以在短时间内转化为 α-生育酚、α-生育三烯酚、代达林 A 和英格列酮。此外，具有不饱和侧链的卤化产物可在自由基环化条件下提供多环加合物。
• Hydroacylation of Alkyl Vinyl Ketones and Acrylic Esters Using Organotetracarbonylferrates. Synthesis of 1,4-Dicarbonyl Compounds
  作者：Masakazu Yamashita、Haruyoshi Tashika、Masaya Uchida

  DOI：10.1246/bcsj.65.1257

  日期：1992.5

  Alkyl vinyl ketones and acrylic esters were hydroacylated with organotetracarbonylferrates to the corresponding 1,4-diketones and 4-oxo carboxylic acid derivatives in good yield in dipolar aprotic solvents such as N,N-dimethylacetamide. Addition of 18-crown-6 improved the yield. cis-Jasmone and γ-jasmolactone were synthesized by use of these reactions.

  烷基乙烯基酮和丙烯酸酯在偶极非质子溶剂（如 N，N-二甲基乙酰胺）中用有机四羰基高铁酸盐氢化酰化为相应的 1,4-二酮和 4-氧代羧酸衍生物。添加 18-crown-6 提高了产量。利用这些反应合成了顺式茉莉酮和γ-茉莉酸内酯。
• Cooperative Activation with Chiral Nucleophilic Catalysts and<i>N</i>-Haloimides: Enantioselective Iodolactonization of 4-Arylmethyl-4-pentenoic Acids
  作者：Hidefumi Nakatsuji、Yasuhiro Sawamura、Akira Sakakura、Kazuaki Ishihara

  DOI：10.1002/anie.201400946

  日期：2014.7.1

  Chiral triaryl phosphates promote the enantioselective iodolactonization of 4‐substituted 4‐pentenoic acids to give the corresponding iodolactones in high yields with high enantioselectivity. N‐Chlorophthalimide (NCP) is employed as a Lewis acidic activator and oxidant of I2 for the present iodolactonization. In combination with 1.5 equivalents of NCP, only 0.5 equivalents of I2 are sufficient to generate

  手性磷酸三芳基酯促进4-取代的4-戊烯酸的对映选择性碘内酯化，以高收率和高对映选择性产生相应的碘内酯。N-氯邻苯二甲酰亚胺（NCP）被用作本碘代内酯化的路易斯酸性活化剂和I 2的氧化剂。与1.5当量的NCP结合，仅0.5当量的I 2足以产生碘化试剂。
• Synthesis of saturated primary-secondary ?-glycols
  作者：V. G. Bukharov、T. E. Pozdnyakova

  DOI：10.1007/bf00909415

  日期：1961.1