hexane-1,6-diyl bis(phenylacetate) | 521294-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: hexane-1,6-diyl bis(phenylacetate)
• 英文别名: 1,6-bis(2-phenylacetyloxy)hexane；1,6-bis-phenylacetoxy-hexane；1,6-Bis-phenylacetoxy-hexan；phenyl-acetic acid 6-phenylacetoxy-hexyl ester；6-(2-Phenylacetyl)oxyhexyl 2-phenylacetate
• CAS: 521294-03-1
• 化学式: C₂₂H₂₆O₄
• 分子量: 354.446
• InChiKey: XVGRIJPGZOKMNE-UHFFFAOYSA-N

物化性质

• 沸点：
  481.7±33.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  hexane-1,6-diyl bis(phenylacetate) 在 四丁基碘化铵 、 potassium carbonate 、 paraformaldehyde 作用下， 以 乙醚 、 甲苯 为溶剂， 以2.53 g (27%)的产率得到2-phenyl-acrylic acid 6-(2-phenyl-acryloyloxy)-hexyl Ester
  参考文献：
  名称：

  Stabilization of Organic Materials

  摘要：

  该发明描述了一种用于稳定有机材料抵抗氧化、热降解或光诱导降解的过程，其中包括将化合物（I）至少混入其中或应用于其中，其中通式中的一般符号如权利要求1所定义。通式I的化合物特别适用作合成聚合物的加工稳定剂。

  公开号：

  US20080269382A1
• 作为产物：
  描述：

  苯乙酸 、 1,6-己二醇 在 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.17h， 以83%的产率得到hexane-1,6-diyl bis(phenylacetate)
  参考文献：
  名称：

  Efficient and Controllably Selective Preparation of Esters Using Uronium-Based Coupling Agents

  摘要：

  Carboxylic acid esters can be prepared in excellent yields at room temperature from an acid and either a phenol or an aliphatic alcohol using Me peptide coupling reagents, TBTU, TATU, or COMU, in the presence of organic bases. Reactions using TBTU and TATU are faster but do not occur with tertiary alcohols. Selectivity between reaction with primary or secondary alcohols in diols and polyols can be achieved with choice of base and coupling agent.

  DOI：

  10.1021/ol201005s

文献信息

• Amide/Iminium Zwitterionic Catalysts for (Trans)esterification: Application in Biodiesel Synthesis
  作者：Ying-Pong Lam、Xinyan Wang、Fei Tan、Wing-Hin Ng、Ying-Lung Steve Tse、Ying-Yeung Yeung

  DOI：10.1021/acscatal.9b01959

  日期：2019.9.6

  organocatalysts based on an amide anion/iminium cation charge pair has been developed. The zwitterions are easily prepared by reacting aziridines with aminopyridines. They are catalytically applicable to transesterifications and dehydrative esterifications. Mechanistic studies reveal that the amide anion and iminium cation work synergistically in activating the reaction partners, with the iminium cationic

  已经开发了一类基于酰胺阴离子/亚胺阳离子电荷对的两性离子有机催化剂。两性离子易于通过使氮丙啶与氨基吡啶反应来制备。它们催化地适用于酯交换和脱水酯化。机理研究表明，酰胺阴离子和亚胺阳离子在活化反应伙伴方面具有协同作用，亚胺阳离子部分通过非经典氢键与羰基底物相互作用。该反应可在温和条件下用于大规模合成生物柴油。
• ZWITTERIONIC CATALYSTS FOR (TRANS)ESTERIFICATION: APPLICATION IN FLUOROINDOLE-DERIVATIVES AND BIODIESEL SYNTHESIS
  申请人：The Chinese University of Hong Kong

  公开号：US20210023539A1

  公开（公告）日：2021-01-28

  An amide/iminium zwitterion catalyst has a catalyst pocket size that promotes transesterification and dehydrative esterification. The amide/iminium zwitterions are easily prepared by reacting aziridines with aminopyridines. The reaction can be applied a wide variety of esterification processes including the large-scale synthesis of biodiesel. The amide/iminium zwitterions allow the avoidance of strongly basic or acidic condition and avoidance of metal contamination in the products. Reactions are carried out at ambient or only modestly elevated temperatures. The amide/iminium zwitterion catalyst is easily recycled and reactions proceed in high to quantitative yields.

  一种酰胺/亚胺兹维特离子催化剂具有促进酯交换和脱水酯化的催化剂口袋尺寸。酰胺/亚胺兹维特离子通过将环氮烷与氨基吡啶反应而容易制备。该反应可应用于各种酯化过程，包括生物柴油的大规模合成。酰胺/亚胺兹维特离子可避免强碱性或酸性条件，并避免产品中的金属污染。反应在常温或仅略微升温下进行。酰胺/亚胺兹维特离子催化剂易于回收，反应产率高且接近定量。
• A Lewis acid-promoted Pinner reaction
  作者：Dominik Pfaff、Gregor Nemecek、Joachim Podlech

  DOI：10.3762/bjoc.9.179

  日期：——

  Carbonitriles and alcohols react in a Lewis acid-promoted Pinner reaction to carboxylic esters. Best results are obtained with two equivalents of trimethylsilyl triflate as Lewis acid. Good yields are achieved with primary alcohols and aliphatic or benzylic carbonitriles, but the straightforward synthesis of acrylates and benzoates starting with acrylonitrile and benzonitrile, respectively, is similarly possible. Phenols are not acylated under these reaction conditions. The method has been used for the first total synthesis of the natural product monaspilosin. In the reaction of benzyl alcohols variable amounts of amides are formed in a Ritter-type side reaction.

  Carbonitriles和醇在Lewis酸促进的Pinner反应中反应生成羧酸酯。最佳结果是使用两当量的三甲基硅酰三氟甲烷作为Lewis酸。一次醇和脂肪族或苄基腈可以获得良好产率，但使用丙烯腈和苯甲腈分别合成丙烯酸酯和苯甲酸酯也同样可行。苯酚在这些反应条件下不会酰化。该方法已被用于天然产物单孢氨基脂的首次全合成。在苄醇的反应中，会形成不同量的酰胺，这是一种Ritter型的副反应。
• Four acid-catalysed dehydration reactions proceed without interference
  作者：Rio Carlo Lirag、Ognjen Š. Miljanić

  DOI：10.1039/c4cc02990a

  日期：——

  Four acid-catalysed dehydration reactions can proceed in one pot, simultaneously and without interference, to yield one imine, one acetal (or boronic ester), one ester and one alkene, even though many other cross-products could be conceived. This advanced self-sorting behaviour is attributed to different dehydration rates, brought about by dissimilar electronic properties of starting materials.

  即使可以设想许多其他交叉产物，也可以在一个反应​​釜中同时进行四个酸催化的脱水反应，而不会产生干扰，从而生成一种亚胺，一种乙缩醛（或硼酸酯），一种酯和一种烯烃。这种先进的自选行为归因于不同的脱水速率，这是由起始原料的不同电子特性引起的。
• Tabenkin et al., Archives of Biochemistry, 1952, vol. 38, p. 43,44
  作者：Tabenkin et al.

  DOI：——

  日期：——