1-(4-methoxy-phenyl)-tetradecan-1-one | 102456-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-methoxy-phenyl)-tetradecan-1-one
• 英文别名: 1-(4-Methoxy-phenyl)-tetradecan-1-on；4-Myristoylanisole；1-(4-methoxyphenyl)tetradecan-1-one
• CAS: 102456-30-4
• 化学式: C₂₁H₃₄O₂
• 分子量: 318.5
• InChiKey: QPEFYYXRDDRXOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-methoxy-phenyl)-tetradecan-1-one 在 montmorillonite K-10 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 dimethyl (4R,5R)-2-(4-methoxyphenyl)-2-tridecyl-1,3-dioxolane-4,5-dicarboxylate
  参考文献：
  名称：

  新型手性和外消旋1,3-二氧戊环的合成

  摘要：

  合成了一系列手性1,3-二氧戊环3 – 12，ee值> 99％。这是从酮与芳基，单取代的芳基和长烷基链（C 11 -AC 13）开始的手性缩酮化反应的首次研究。其EE值通过在Chiralcel OD柱上的手性高效液相色谱法（HPLC）测定，使用它们的外消旋的1,3-二恶戊环外消旋3 - 12，这也被合成为第一次。这些手性和外消旋的1,3-二氧戊环酮通过红外，NMR（1 H，13 C），质谱，元素分析，旋光和手性HPLC进行表征。

  DOI：

  10.1002/jhet.937
• 作为产物：
  描述：

  苯甲醚 、 肉豆蔻酰氯 生成 1-(4-methoxy-phenyl)-tetradecan-1-one
  参考文献：
  名称：

  新型手性和外消旋1,3-二氧戊环的合成

  摘要：

  合成了一系列手性1,3-二氧戊环3 – 12，ee值> 99％。这是从酮与芳基，单取代的芳基和长烷基链（C 11 -AC 13）开始的手性缩酮化反应的首次研究。其EE值通过在Chiralcel OD柱上的手性高效液相色谱法（HPLC）测定，使用它们的外消旋的1,3-二恶戊环外消旋3 - 12，这也被合成为第一次。这些手性和外消旋的1,3-二氧戊环酮通过红外，NMR（1 H，13 C），质谱，元素分析，旋光和手性HPLC进行表征。

  DOI：

  10.1002/jhet.937

文献信息

• Manganese Complex Catalyzed Sequential Multi‐component Reaction: Enroute to a Quinoline‐Derived Azafluorenes
  作者：Avijit Mondal、Debjyoti Pal、Hirak Jyoti Phukan、Mithu Roy、Saurabh Kumar、Siddhartha Purkayastha、Ankur Kanti Guha、Dipankar Srimani

  DOI：10.1002/cssc.202301138

  日期：2024.4.8

  A sustainable sequential multicomponent method for the synthesis of highly functionalized quinolines from renewable starting materials was shown via manganese catalysis. The synthesized quinoline derivatives were further utilized to prepare new type of quinoline derived azafluorenes via unprecedented direct C(sp3)−H bond hydroxylation and Friedel–Crafts-type annulation.

  通过锰催化，展示了一种可持续的顺序多组分方法，用于从可再生原材料合成高功能化的喹啉。合成的喹啉衍生物通过前所未有的直接C(sp 3 )−H键羟基化和Friedel-Crafts型成环进一步用于制备新型喹啉衍生的氮杂芴。
• Asymmetric synthesis of new chiral long chain alcohols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2010.12.010

  日期：2010.12

  Sixteen new chiral alcohols with alkyl (C-11-C-19) and aryl, substituted aryl, hetero aryl and biaryl groups 2a-2t were synthesized by three different asymmetric reduction methods from their corresponding ketones 1a-1t. Chiral NaBH4 (method A), chiral BH3 (method B) and chiral AIP (method C) were used as asymmetric reduction catalysts. Chiral NaBH4 was modified by four different ligands 3a-3d, chiral BH3 and chiral AIP by four different ligands 4a-4d. Ligand 4c was synthesized for the first time in this work. Chiral NaBH4 generated chiral alcohols of (R)-configuration and chiral BH3 and chiral AIP of (S)-configuration with high enantiomeric excesses, were analysed by chiral HPLC. In order to determine the ee values by chiral HPLC, sixteen corresponding racemic alcohols, synthesized by reducing their corresponding ketones via NaBH4, were used for chiral resolution on a Daicel OD HPLC column. The sixteen starting ketones were synthesized in this study by Friedel-Craft acylation. The new chiral alcohols were characterized by IR, NMR, (H-1 and C-13), MS, elemental analyses and specific rotation. The reduction methods A, B and C were applied to these ketones for the first time in this study and were compared with each other. The relationship between the structure of the ketone and the yield and the enantiomeric excess was discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of new chiral 1,2- and 1,3-diols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1007/s00706-012-0792-7

  日期：2013.2

  Seven chiral 1,2-diols and six chiral 1,3-diols were synthesized by the asymmetric reduction of the corresponding 1,2-diketones and 1,3-diketones using oxazaborolidine-BH3 catalyst. The 13 corresponding racemic 1,2- and 1,3-diols were synthesized by reducing the diketones with NaBH4 and they were used for determining the ee values through their chiral resolution on HPLC and GC. Five starting diketones, four racemic 1,2-diols, five chiral 1,2-diols, and two chiral 1,3-diols are novel compounds. The new chiral compounds were characterized by IR, H-1 and C-13 NMR, MS, and elemental analysis. The asymmetric reduction method, oxazaborolidine-BH3, was applied to these diketones for the first time in this study. The relationship between the structure of the diketone and the yield, diastereoselectivity, and enantiomeric excess was discussed.
• Majima; Nagaoka; Keisuke, Chemische Berichte, 1922, vol. 55, p. 216
  作者：Majima、Nagaoka、Keisuke

  DOI：——

  日期：——
• Synthesis of new (R)-secondary carbinols with different structures via enzymatic resolution
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2011.07.017

  日期：2011.6

  The present study deals with the biocatalytic enantioselective synthesis of 19 new chiral alcohols with alkyl (C-11-C-19) and phenyl, substituted phenyl, heteroaromatic, and naphthyl groups 4a-4z with an (R)-configuration and high enantiomeric excess (similar to 100%). The corresponding ketones 1a-1z were synthesized and then reduced with NaBH4 to their racemic alcohols 2a-2z, which were converted into their racemic acetyl derivatives 3a-3z. Enzymes of four different types were used for the enantioselective hydrolysis of these acetyl compounds 3a-3z. The optimal reaction conditions for these four enzymes were established by investigating the enantiomeric excesses by chiral HPLC. Amano lipase from Burkholderica cepacia (Pseudomonas cepacia) AL-PS was determined as the best enzyme in this work This study presents an environmentally friendly and green chemistry method for the synthesis of these new (R)-chiral carbinols 4a-4z. (C) 2011 Elsevier Ltd. All rights reserved.