oleyl phenylacetate | 51677-71-5

• 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: oleyl phenylacetate
• 英文别名: phenyl-acetic acid octadec-9c-enyl ester；Phenyl-essigsaeure-octadec-9c-enylester；[(Z)-octadec-9-enyl] 2-phenylacetate
• CAS: 51677-71-5
• 化学式: C₂₆H₄₂O₂
• 分子量: 386.618
• InChiKey: CDJQPUDEGWOPFV-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.6
• 重原子数：
  28
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  oleyl phenylacetate 在 对甲苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 生成 (Z)-octadec-9-en-1-yl 2-diazo-2-phenylacetate
  参考文献：
  名称：

  可见光促进的多取代烯烃合成，涉及硫叶立德作为碳捕集剂

  摘要：

  描述了一种蓝色发光二极管（LED），其促进了重氮芳基乙酸酯与硫酰化物的偶联。该方案具有温和的条件，良好的官能团耐受性以及芳基重氮乙酸酯和硫酰化物的广泛底物范围。在最佳反应条件下，以中等至良好的收率获得了广泛的三取代烯烃，经过两步简单的操作，即可将其进一步转移至其他对生物重要的杂环上。

  DOI：

  10.1021/acs.joc.0c02500
• 作为产物：
  描述：

  苯乙酸 、 油醇 在 盐酸 作用下， 生成 oleyl phenylacetate
  参考文献：
  名称：

  Tabenkin et al., Archives of Biochemistry, 1952, vol. 38, p. 43,44

  摘要：

  DOI：

文献信息

• Visible <scp>Light‐Promoted</scp> Sulfoxonium Ylides Synthesis from Aryl Diazoacetates and Sulfoxides
  作者：Juan Lu、Lei Li、Xiang‐Kui He、Guo‐Yong Xu、Jun Xuan

  DOI：10.1002/cjoc.202100064

  日期：2021.6

  A visible light-promoted reaction of donor/acceptor diazoalkanes with sulfoxides towards the synthesis of synthetically useful sulfoxonium ylides was reported. The reaction occurred under sole visible light irradiation without the need of any transition-metals or additives, affording the corresponding sulfoxonium ylides in moderate to good yields. The success of late-stage modification of natural isolates

  据报道，供体/受体重氮烷烃与亚砜在可见光促进下反应，可合成合成有用的亚磺酰基。该反应在单独的可见光照射下进行，不需要任何过渡金属或添加剂，以中等至良好的产率提供了相应的sulf基。天然分离物或候选药物的后期修饰，放大反应以及将亚砜基鎓盐转化为其他有用分子的成功成功进一步使该方法有价值。
• Visible light and base promoted O-H insertion/cyclization of para-quinone methides with aryl diazoacetates: An approach to 2,3-dihydrobenzofuran derivatives
  作者：Shuangjing Zhou、Baogui Cai、Chuxia Hu、Xu Cheng、Lei Li、Jun Xuan

  DOI：10.1016/j.cclet.2021.03.010

  日期：2021.8
• Lipophilic (Hydroxy)phenylacetates by Solvent-Free Lipase-Catalyzed Esterification and Transesterification in Vacuo
  作者：Petra Weitkamp、Nikolaus Weber、Klaus Vosmann

  DOI：10.1021/jf8002224

  日期：2008.7.1

  Various long-chain alkyl (hydroxy)phenylacetates were prepared in high yield by lipase-catalyzed transesterification of the corresponding short-chain alkyl hydroxyphenyl acetates and fatty alcohols in equimolar ratios. The reactions were performed in vacuo at moderate temperatures in the absence of solvents and drying agents in direct contact with the reaction mixture. Immobilized lipase B from Candida antarctica(Novozym 435) was the most effective biocatalyst for the various transesterification reactions. Generally, Novozym 435-catalyzed transesterifications of short-chain alkyl (hydroxy)phenylacetates with long-chain alcohols led to higher conversions and enzyme activities than the corresponding esterifications. For example, the transesterification activity was up to 4-fold higher than the esterification activity for the formation of oleyl 4-hydroxy-3-methoxyphenylacetate using Novozym 435 as a biocatalyst. The relative transesterification activities were as follows: phenylacetate > 3-methoxyphenylacetate approximate to 4-methoxyphenylacetate > 4-hydroxy-3-methoxyphenylacetate > 3-hydroxyphenylacetate approximate to 4-hydroxyphenylacetate >> 2-methoxyphenylacetate >> 3,4-dihydroxyphenylacetate. With respect to the position of methoxy and hydroxy substituents, the transesterification activity of Novozym 435 decreased in the order meta approximate to para >> ortho. Compounds with inverse chemical structures, for example, tyrosyl oleate, were obtained by Novozym 435-catalyzed esterification and transesterification of fatty acids and their methyl esters, respectively, with 2-phenylethan-1-ols. In contrast to the transesterifications of short-chain alkyl (hydroxy)phenylacetates with fatty alcohols, higher conversions and enzyme activities were observed for the Novozym 435-catalyzed esterifications of (hydroxy)phenylethanols with long-chain fatty acids than the corresponding transesterifications with fatty acid methyl esters.
• ENANTIOMERS OF AMINO-PHENYL-ACETIC ACID OCTADEC- 9- (Z) ENYL ESTER, THEIR SALTS AND THEIR USES
  申请人：Yeda Research And Development Co. Ltd. At The Weizmann Institute of Science

  公开号：EP2114155A1

  公开（公告）日：2009-11-11
• USE OF LONG-CHAIN ALCOHOL DERIVATIVES FOR THE TREATMENT OF ALOPECIA AREATA
  申请人：Yeda Research And Development Co. Ltd. At The Weizmann Institute of Science

  公开号：EP2117301A1

  公开（公告）日：2009-11-18