cis-Octadecen-9-saeurephenacylester | 90144-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-Octadecen-9-saeurephenacylester
• 英文别名: phenacyl (Z)-octadec-9-enoate
• CAS: 90144-64-2
• 化学式: C₂₆H₄₀O₃
• 分子量: 400.602
• InChiKey: YJDYLKBQHAXVOQ-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  cis-Octadecen-9-saeurephenacylester 在 N,N,N',N'-四甲基-O-亚苯基二胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以100%的产率得到油酸
  参考文献：
  名称：

  Protecting Groups That Can Be Removed through Photochemical Electron Transfer:  Mechanistic and Product Studies on Photosensitized Release of Carboxylates from Phenacyl Esters

  摘要：

  Photolysis of electron-donating photosensitizers in the presence of various phenacyl esters (PhCOCH2-OCOR) results in C-O bond scission leading to the formation of acetophenone (PhCOCH3) and the corresponding carboxylic acid(RCO2H). Preparative experiments showed that the carboxylic acids are generated in high or quantitative isolated yields. It is argued that this reaction is initiated by a photoinduced electron transfer from the excited state sensitizer to the phenacyl ester. The latter process forms the anion radical of the phenacyl ester which in turn undergoes rapid C-O bond scission leading to the phenacyl radical and the corresponding carboxylate anion. This mechanism is supported by the following observations. (1) The phenacyl esters quench fluorescence from the sensitizers. (2) Analysis of the redox potentials of the sensitizer excited states and the substrates shows that the proposed electron transfer step is exergonic by 15-20 kcal/mol. (3) The byproducts are indicative of the proposed ion radical intermediates. In particular N-methylaniline is detected when N,N-dimethylaniline is used as a sensitizer. (4) Competing processes are observed in phenacyl esters whose acid components are themselves labile to single-electron transfer. For example, phenacyl 4-bromophenylacetate showed bromide elimination in competition with deprotection.

  DOI：

  10.1021/jo970495j
• 作为产物：
  描述：

  油酸 、 2-溴苯乙酮 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 反应 2.0h， 以95%的产率得到cis-Octadecen-9-saeurephenacylester
  参考文献：
  名称：

  Protecting Groups That Can Be Removed through Photochemical Electron Transfer:  Mechanistic and Product Studies on Photosensitized Release of Carboxylates from Phenacyl Esters

  摘要：

  Photolysis of electron-donating photosensitizers in the presence of various phenacyl esters (PhCOCH2-OCOR) results in C-O bond scission leading to the formation of acetophenone (PhCOCH3) and the corresponding carboxylic acid(RCO2H). Preparative experiments showed that the carboxylic acids are generated in high or quantitative isolated yields. It is argued that this reaction is initiated by a photoinduced electron transfer from the excited state sensitizer to the phenacyl ester. The latter process forms the anion radical of the phenacyl ester which in turn undergoes rapid C-O bond scission leading to the phenacyl radical and the corresponding carboxylate anion. This mechanism is supported by the following observations. (1) The phenacyl esters quench fluorescence from the sensitizers. (2) Analysis of the redox potentials of the sensitizer excited states and the substrates shows that the proposed electron transfer step is exergonic by 15-20 kcal/mol. (3) The byproducts are indicative of the proposed ion radical intermediates. In particular N-methylaniline is detected when N,N-dimethylaniline is used as a sensitizer. (4) Competing processes are observed in phenacyl esters whose acid components are themselves labile to single-electron transfer. For example, phenacyl 4-bromophenylacetate showed bromide elimination in competition with deprotection.

  DOI：

  10.1021/jo970495j

文献信息

• CHRISTIE, WILLIAM W.;MCG. , BRECKENRIDGE GRACE H., J. CHROMATOGR., 469,(1989) C. 261-269
  作者：CHRISTIE, WILLIAM W.、MCG. , BRECKENRIDGE GRACE H.

  DOI：——

  日期：——
• HANIS, TOMAS;SMRZ, MIROSLAV;KLIR, PAVEL;MACEK, KAREL;KLIMA, JOSEF;BASE, J+, J. CHROMATOGR., 452,(1988) C. 443-457
  作者：HANIS, TOMAS、SMRZ, MIROSLAV、KLIR, PAVEL、MACEK, KAREL、KLIMA, JOSEF、BASE, J+

  DOI：——

  日期：——
• METHOD TO PRODUCE ACETYLDIACYLGLYCEROLS (AC-TAGS) BY EXPRESSION OF AN ACETYLTRANSFERASE GENE ISOLATED FROM EUONYMUS ALATUS (BURNING BUSH)
  申请人：Durrett Timothy

  公开号：US20130116462A1

  公开（公告）日：2013-05-09

  The present invention relates to novel diacylglycerol acyltransferase genes and proteins, and methods of their use. In particular, the invention describes genes encoding proteins having diacylglycerol acetyltransferase activity, specifically for transferring an acetyl group to a diacylglycerol substrate to form acetyl-Triacylglycerols (ac-TAGS), for example, a 3-acetyl-1,2-diacyl-sn-glycerol. The present invention encompasses both native and recombinant wild-type forms of the transferase, as well as mutants and variant forms. The present invention also relates to methods of using novel diacylglycerol acyltransferase genes and proteins, including their expression in transgenic organisms at commercially viable levels, for increasing production of 3-acetyl-1,2-diacyl-sn-glycerols in plant oils and altering the composition of oils produced by microorganisms, such as yeast, by increasing ac-TAG production. Additionally, oils produced by methods of the present inventions comprising genes and proteins are contemplated for use as biodiesel fuel, in polymer production and as naturally produced food oils with reduced calories.
• US9328335B2
  申请人：——

  公开号：US9328335B2

  公开（公告）日：2016-05-03
• [EN] A METHOD TO PRODUCE ACETYLDIACYLGLYCEROLS (AC-TAGS) BY EXPRESSION OFAN ACETYLTRANSFERASE GENE ISOLATED FROM EUONYMUS ALATUS (BURNING BUSH)<br/>[FR] PROCÉDÉ DE PRODUCTION D'ACÉTYLDIACYLGLYCÉROLS (AC-TAG) PAR EXPRESSION D'UN GÈNE D'ACÉTYLTRANSFÉRASE ISOLÉ À PARTIR D'EUONYMUS ALATUS (FUSAIN AILÉ)
  申请人：UNIV MICHIGAN STATE

  公开号：WO2011082253A2

  公开（公告）日：2011-07-07

  The present invention relates to novel diacylglycerol acyltransferase genes and proteins, and methods of their use. In particular, the invention describes genes encoding proteins having diacylglycerol acetyltransferase activity, specifically for transferring an acetyl group to a diacylglycerol substrate to form acetyl- Triacylglycerols (ac-TAGs), for example, a 3-acetyl-1,2-diacyl-sn-glycerol. The present invention encompasses both native and recombinant wild-type forms of the transferase, as well as mutants and variant forms. The present invention also relates to methods of using novel diacylglycerol acyltransferase genes and proteins, including their expression in transgenic organisms at commercially viable levels, for increasing production of 3 -acetyl- 1,2-diacyl-sn-glycerols in plant oils and altering the composition of oils produced by microorganisms, such as yeast, by increasing ac- TAG production. Additionally, oils produced by methods of the present inventions comprising genes and proteins are contemplated for use as biodiesel fuel, in polymer production and as naturally produced food oils with reduced calories.