methyl 2-acetyltetradecanoate | 357914-49-9

• 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
• 英文名称: methyl 2-acetyltetradecanoate
• 英文别名: 2-Acetyl-tetradecanoic acid methyl ester；Methyl 2-acetyltetradecanoate
• CAS: 357914-49-9
• 化学式: C₁₇H₃₂O₃
• 分子量: 284.439
• InChiKey: RMZDRWPZKKDODO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  methyl 2-acetyltetradecanoate 在 水 、 sodium 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 3-methylpentadecan-2-one
  参考文献：
  名称：

  天然产物的小型组合图书馆的合成：菊粉（Inula helenium L。）（菊科）根精油中新的长链3-甲基-2-链烷酮的鉴定和定量

  摘要：

  最近，有报道称菊粉菊（Inula helenium L.（Asteraceae））根精油具有强大的抗葡萄球菌活性。此外，油的生物测定指导分馏指出，杜仲倍半萜烯内酯和一系列未确定的成分是观察到的活性的主要载体。

  DOI：

  10.1002/pca.2466
• 作为产物：
  描述：

  [4-[(E)-2-(4-phenylphenyl)ethenyl]phenyl]methyl 2-acetyltetradecanoate 在 甲醇 、 TEA 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到methyl 2-acetyltetradecanoate
  参考文献：
  名称：

  Precipiton strategies applied to the isolation of α-substituted β-ketoesters

  摘要：

  Diaryl alkene 1Z is a 'precipiton', a protecting group that allows reaction products to be isolated by simple filtration. Here we illustrate the use of this protecting group for the preparation and isolation, without distillation or chromatography, of pure cc-substituted beta -ketoesters. The precipiton 1Z was prepared in 43% overall yield. It is anticipated that development of precipiton-based syntheses will provide a new alternative for automated reaction product isolation that may be useful for bench-scale and process-scale chemical preparations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00726-2

文献信息

• Catalytic Asymmetric Homologation of Ketones with α-Alkyl α-Diazo Esters
  作者：Fei Tan、Maoping Pu、Jun He、Jinzhao Li、Jian Yang、Shunxi Dong、Xiaohua Liu、Yun-Dong Wu、Xiaoming Feng

  DOI：10.1021/jacs.0c12683

  日期：2021.2.10

  derivatives with α-alkyl α-diazo esters utilizing a chiral scandium(III) N,N′-dioxide as the Lewis acid catalyst. This reaction supplies a highly chemo-, regio-, and enantioselective pathway for the synthesis of optically active β-keto esters with an all-carbon quaternary center through highly selective alkyl-group migration of the ketones. Moreover, the ring expansion of cyclic ketones was accomplished under

  酮与重氮化合物的同源性是合成单碳扩链无环酮或扩环环酮的有用策略。然而，由于较低的反应性和复杂的选择性，无环酮与α-重氮酯的不对称同源性仍然是一个挑战。在此，我们报道了利用手性scan（III）N，N与N -α-烷基α-重氮酯对苯乙酮和相关衍生物的对映选择性催化同源性'-二氧化物为路易斯酸催化剂。该反应提供了高度化学，区域和对映体选择性的途径，用于通过酮的高选择性烷基基团迁移来合成具有全碳季中心的旋光性β-酮酯。此外，环状酮的扩环是在稍微修饰的条件下完成的，从而提供了一系列对映体富集的环状β-酮酯。已经进行了密度泛函理论计算，以阐明可以解释所观察到的区域和对映选择性的反应途径和可能的工作模型。
• Cobalt(II) acetate promoted addition of acetoacetate to terminal olefins: A highly stereoselective synthesis of 5-alkyl-2-hydroxy 2 methyl-3-methoxycarbonyl tetrahydrofurans
  作者：Javed Iqbal、T.K.Praveen Kumar、S. Manogaran

  DOI：10.1016/s0040-4039(01)80778-4

  日期：1989.1

  Methylacetoacetate and terminal olefins react in presence of Cobalt(II) acetate and Oxygen to give the titled compound(2) in a highly stereoselective manner and the structure of this compound is elucidated by 1H NMR simulation studies.

  乙酰乙酸甲酯和末端烯烃在乙酸钴（II）和氧气的存在下反应，以高度立体选择性的方式得到标题化合物（2），并且该化合物的结构通过1 H NMR模拟研究得以阐明。
• A photo-responsive fluorescent amphiphile for target-specific and image-guided drug delivery applications
  作者：Subhasis Dey、Plaboni Sen、Anjali Patel、Biswa Mohan Prusty、Siddhartha Sankar Ghosh、Debasis Manna

  DOI：10.1039/d2ob01332k

  日期：——

  CYsome: an acetazolamide grafted cyanine-3-based macrocyclic amphiphile demonstrates target-specificity, biocompatibility, self-imaging, and a NIR-responsive release profile for image-guided chemotherapeutic applications.

  CYsome：一种以乙酰唑胺为基础的青光菌素-3基团结构的大环性分子两亲性分子，具有靶向特异性、生物相容性、自成像和近红外响应释放特性，可用于图像引导的化疗应用。
• Rhodium-mediated cyclopentane construction can compete with .beta.-hydride elimination: synthesis of (.+-.)-tochuinyl acetate
  作者：Douglass F. Taber、Michael J. Hennessy、James P. Louey

  DOI：10.1021/jo00028a011

  日期：1992.1

  Rhodium(II) carboxylate catalyzed C-H insertion to form a cyclopentane is shown to compete effectively with beta-hydride elimination, except when the beta-hydrogen is ternary. Cyclization of diazo ester 27 gives 28, which is converted in three steps to (+/-)-tochuinyl acetate 25. Both the cyclization to form 28 and the alkylation of 28 proceed with remarkable diastereoselectivity.
• Precipiton strategies applied to the isolation of α-substituted β-ketoesters
  作者：Todd Bosanac、Craig S Wilcox

  DOI：10.1016/s0040-4039(01)00726-2

  日期：2001.6

  Diaryl alkene 1Z is a 'precipiton', a protecting group that allows reaction products to be isolated by simple filtration. Here we illustrate the use of this protecting group for the preparation and isolation, without distillation or chromatography, of pure cc-substituted beta -ketoesters. The precipiton 1Z was prepared in 43% overall yield. It is anticipated that development of precipiton-based syntheses will provide a new alternative for automated reaction product isolation that may be useful for bench-scale and process-scale chemical preparations. (C) 2001 Elsevier Science Ltd. All rights reserved.