13-ketotetradecanoic acid methyl ester | 18993-10-7

• 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: 13-ketotetradecanoic acid methyl ester
• 英文别名: methyl 13-oxo tetradecanoate；13-keto tetradecanoic acid methyl ester；13-oxo-tetradecanoic acid methyl ester；methyl 13-oxotetradecanoate
• CAS: 18993-10-7
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: RPMDDORIKABZOA-UHFFFAOYSA-N

物化性质

• 沸点：
  100-110 °C(Press: 2.4e-2 Torr)
• 密度：
  0.926±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  13-ketotetradecanoic acid methyl ester 在 盐酸 、 lithium aluminium tetrahydride 、 titanium(III) chloride 、 三乙胺 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 30.0h， 生成 2-methylcyclotridecanone
  参考文献：
  名称：

  Titanium-induced cyclization of keto esters: a new method of cycloalkanone synthesis

  摘要：

  DOI：

  10.1021/ja00344a045
• 作为产物：
  描述：

  11-溴十一酸甲酯 生成 13-ketotetradecanoic acid methyl ester
  参考文献：
  名称：

  Neue大环内酯和益生菌倍半萜衍生物-Galz -Harz

  摘要：

  新的大环内酯类化合物和一些加倍青素中的倍半萜衍生物

  DOI：

  10.1002/hlca.19780610736

文献信息

• Temporal separation of catalytic activities allows anti-Markovnikov reductive functionalization of terminal alkynes
  作者：Le Li、Seth B. Herzon

  DOI：10.1038/nchem.1799

  日期：2014.1

  There is currently great interest in the development of multistep catalytic processes in which one or several catalysts act sequentially to rapidly build complex molecular structures. Many enzymes—often the inspiration for new synthetic transformations—are capable of processing a single substrate through a chain of discrete, mechanistically distinct catalytic steps. Here, we describe an approach to emulate the efficiency of these natural reaction cascades within a synthetic catalyst by the temporal separation of catalytic activities. In this approach, a single catalyst exhibits multiple catalytic activities sequentially, allowing for the efficient processing of a substrate through a cascade pathway. Application of this design strategy has led to the development of a method to effect the anti-Markovnikov (linear-selective) reductive functionalization of terminal alkynes. The strategy of temporal separation may facilitate the development of other efficient synthetic reaction cascades. Multifunctional catalysts typically process substrates and intermediates concurrently. Here, a strategy is described to separate catalytic activities in the time domain (temporal separation). Application of this strategy has led to the development of a method to effect the anti-Markovnikov reductive functionalization of terminal alkynes; such an approach may facilitate the development of other synthetic reaction cascades.

  目前，发展多步催化过程备受关注，其中一个或多个催化剂按顺序作用，以快速构建复杂分子结构。许多酶——通常是新合成转化的灵感来源——能够通过一系列离散的、机制上不同的催化步骤处理单一底物。在这里，我们描述了一种通过催化活性的时间分离来模拟这些自然反应级联的效率的方法。在这种方法中，单一催化剂按顺序展现多种催化活性，从而允许有效地通过级联路径处理底物。该设计策略的应用促成了一种方法，以实现末端炔烃的反马尔科夫尼科夫（线性选择性）还原官能化。时间分离的策略可能会促进其他高效合成反应级联的发展。多功能催化剂通常同时处理底物和中间体。在这里，描述了一种在时间领域分离催化活性的策略（时间分离）。该策略的应用促成了一种方法，以实现末端炔烃的反马尔科夫尼科夫还原官能化；如此方法可能会促进其他合成反应级联的发展。
• The chemistry of the metasternal gland secretion of the eucalypt longicorn Phoracantha synonyma (Coleoptera : Cerambycidae)
  作者：BP Moore、WV Brown

  DOI：10.1071/ch9761365

  日期：——

  The metasternal gland secretion of Phoracantha synonyma contains a diversity of volatile components, one of which, 2-hydroxy-6-methylbenzaldehyde (1), is of widespread occurrence in the genus. Threemajor components and several minor components are macrocyclic lactones, of which the following have been positively identified: decan-9-olide (2), (2)-dec-4-en-9-olide (3) and 11-hydroxytetradec-5-en-13-olide (4). The methyl and ethyl esters of 2-methylbutyric and related acids are also present and are responsible for the characteristic odour of the fresh secretion.

  胸腺 腺分泌物中含有多种挥发性成分。 含有多种挥发性成分，其中一种是 2-hydroxy-6-methylbenzaldehyde (1)、 2-hydroxy-6-methylbenzaldehyde (1)，在该属中广泛存在。 三种主要成分和 三种主要成分和几种次要成分是大环内酯，其中 癸-9-内酯（2）、(2)-癸-4-烯-9-内酯（3）和 11-羟基十四烷-5-内酯（4）。 11-hydroxytetradec-5-en-13-olide (4).2-甲基丁酸的甲酯和乙酯 2-甲基丁酸和相关酸的甲酯和乙酯，它们是新鲜分泌物特有气味的来源。 新鲜分泌物的特有气味。
• Synthesis, ($E)$/($Z)$-isomerization, and DNA binding, antibacterial, and antifungal activities of novel oximes and $O$-substituted oxime ethers
  作者：Hatice BAŞPINAR KÜÇÜK、Ayşe Sergüzel YUSUFOĞLU、Leyla AÇIK、Betül AYDIN、Leyla ARSLAN

  DOI：10.3906/kim-1604-2

  日期：——

  A series of novel positional oximes (2a-2d), $O$-methyl oxime ethers (3a-3d), and $O$-benzyl oxime ethers (4a-4d) were synthesized in high yields starting from their corresponding methyl 3-, 4-, 6-, and 13-keto tetradecanoates. The synthesized compounds were characterized by $^1}$H NMR, $^13}$C NMR, FT-IR, mass, and elemental analyses for their structures and $(E)$/$(Z)$ isomerizations. Their DNA binding abilities were investigated in vitro by agarose gel electrophoresis. The antibacterial and antifungal activities were tested also in vitro against eleven bacterial strains and three fungal strains. The relationship between the structure and the mentioned biological activities was discussed. Compound 2a showed good antibacterial activity against five types of bacteria. Compounds 2b, 2c, 2d, and 4d were effective against several microorganisms. Among these, 2a showed the best DNA binding, antibacterial, and antifungal activities. Therefore, 2a can be a pro-drug as an anticancer, antibacterial, and antifungal agent.

  从相应的 3-、4-、6-和 13-酮基十四酸甲酯开始，高产率合成了一系列新型位置肟（2a-2d）、$O$-甲基肟醚（3a-3d）和$O$-苄基肟醚（4a-4d）。通过^1}$H NMR、^13}$C NMR、傅立叶变换红外光谱、质量和元素分析，对合成化合物的结构和$(E)$/$(Z)$异构化进行了表征。通过琼脂糖凝胶电泳对它们的 DNA 结合能力进行了体外研究。此外，还对 11 种细菌菌株和 3 种真菌菌株的抗菌和抗真菌活性进行了体外测试。讨论了结构与上述生物活性之间的关系。化合物 2a 对五种细菌具有良好的抗菌活性。化合物 2b、2c、2d 和 4d 对多种微生物有效。其中，2a 的 DNA 结合、抗菌和抗真菌活性最好。因此，2a 可以作为抗癌、抗菌和抗真菌剂的原药。
• Addition of ketones to alkenes
  申请人：QUEST INTERNATIONAL B.V.

  公开号：EP0976714A1

  公开（公告）日：2000-02-02

  The invention provides radical addition of ketone to alkene of the form: where R1 = alkyl R2 = H or alkyl n = 1 to 8 or where R3 = H or lower alkyl R4 = H or lower alkyl m = 2 to 8. The process can be used to produce precursors useful in the production of macrocyclic ketones, particularly muscone.

  该发明提供了将酮基加成到以下形式的烯烃中的基团：其中R1 = 烷基，R2 = H或烷基，n = 1到8，或其中R3 = H或低烷基，R4 = H或低烷基，m = 2到8。该方法可用于生产用于制造大环酮的前体，特别是肉麝香。
• Citterio, Attilio; Ferrario, Francesco; Bernardinis, Silvia De, Journal of Chemical Research, Miniprint, 1983, # 12, p. 2669 - 2683
  作者：Citterio, Attilio、Ferrario, Francesco、Bernardinis, Silvia De

  DOI：——

  日期：——