2-chloro-octadecanal | 603988-52-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 2-chloro-octadecanal
• 英文别名: 2-Chlorooctadecanal
• CAS: 603988-52-9
• 化学式: C₁₈H₃₅ClO
• 分子量: 302.928
• InChiKey: GNHIIABOYVKCMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  20
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲醇 、 2-chloro-octadecanal 在 盐酸 作用下， 反应 1.5h， 生成 2-methoxy-octadecanal
  参考文献：
  名称：

  Strategies for the analysis of chlorinated lipids in biological systems

  摘要：

  Myeloperoxidase-derived HOCl reacts with the vinyl ether bond of plasmalogens yielding alpha-chlorofatty aldehydes. These chlorinated aldehydes can be purified using thin-layer chromatography, which is essential for subsequent analysis of extracts from some tissues such as myocardium. The alpha-chlorofatty aldehyde 2-chlorohexadecanal (2-ClHDA) is quantified after conversion to its pentafluorobenzyl oxime derivative using gas chromatography-mass spectrometry and negative-ion chemical ionization detection. 2-ClHDA accumulates in activated human neutrophils and monocytes, as well as in atherosclerotic lesions and infarcted myocardium. Metabolites of 2-ClHDA have also been identified, including the oxidation product, 2-chlorohexadecanoic acid (2-ClHA), and the reduction product, 2-chlorohexadecanol. 2-ClHA can be quantified using LC-MS with selected reaction monitoring (SRM) detection. 2-ClHA can be omega-oxidized by hepatocytes and subsequently beta-oxidized from the omega-end, leading to the production of the dicarboxylic acid, 2-chloroadipic acid. This dicarboxylic acid is excreted in the urine and can also be quantified using LC-MS methods with SRM detection. Quantitative analyses of these novel chlorinated lipids are essential to identify the role of these lipids in leukocyte-mediated injury and disease. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.freeradbiomed.2012.06.013
• 作为产物：
  描述：

  1-O-(1'-(E)-octadecenyl)-2-O-oleoyl-sn-glycero-3-phosphocholine 在 sodium hypochlorite 、 二乙烯三胺五醋酸 、 sodium chloride 作用下， 反应 0.08h， 生成 2-chloro-octadecanal
  参考文献：
  名称：

  Synthesis and Antioxidant Properties of an Unnatural Plasmalogen Analogue Bearing a trans O-Vinyl Ether Linkage

  摘要：

  To assess the antioxidant behavior of trans-1, we first synthesized trans-allyl ether 4 by opening an (S)-glycidol derivative with an (E)-alk-2-en-ol, and then produced the unnatural E-enol ether 1 by a stereoselective iridium(I)-catalyzed olefin isomerization. Natural cis-1 was preferentially degraded by HOCl and was more protective than trans-1 against lipid peroxidation induced by a free-radical initiator, demonstrating that the geometry of the 1'-alkenyloxy bond participates in the antioxidant defensive role of 1.

  DOI：

  10.1021/ol9009078

文献信息

• N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters
  作者：Fabien Gelat、Atanu Patra、Xavier Pannecoucke、Akkattu T. Biju、Thomas Poisson、Tatiana Besset

  DOI：10.1021/acs.orglett.8b01482

  日期：2018.7.6

  The N-heterocyclic carbene (NHC)-catalyzed trifluoromethylation of alpha-chloro aldehydes was developed, allowing straightforward access to valuable alpha-trifluoromethyl ester derivatives. The unique combination of an electrophilic trifluoromethylation reagent with NHC catalysis was the key for the functionalization of a broad range of alpha-chloro aldehydes, and the products are formed in moderate to good yields. Investigations of the enantioselective version of this reaction afforded the enantioenriched products in moderate yields with good ee values.
• DIAGNOSTIC METHOD FOR BIOMARKERS OF ADVERSE CORONARY EVENTS
  申请人：Ford David A.

  公开号：US20110091980A1

  公开（公告）日：2011-04-21

  A diagnostic method using biomarkers to predict future adverse coronary events is provided. More particularly, the present invention is directed to diagnostic tests for characterizing an individual's risk of developing or having cardiovascular disease. In certain embodiments, the method of the present invention quantitates the presence of elevated levels of chlorinated lipids derived from myeloperoxidase as a prognostic indicator of future adverse coronary events.
• US4097665A
  申请人：——

  公开号：US4097665A

  公开（公告）日：1978-06-27
• US8137978B2
  申请人：——

  公开号：US8137978B2

  公开（公告）日：2012-03-20
• Synthesis and Antioxidant Properties of an Unnatural Plasmalogen Analogue Bearing a trans <i>O</i>-Vinyl Ether Linkage
  作者：Ravi S. Lankalapalli、Joseph T. Eckelkamp、Debajit Sircar、David A. Ford、Papasani V. Subbaiah、Robert Bittman

  DOI：10.1021/ol9009078

  日期：2009.7.2

  To assess the antioxidant behavior of trans-1, we first synthesized trans-allyl ether 4 by opening an (S)-glycidol derivative with an (E)-alk-2-en-ol, and then produced the unnatural E-enol ether 1 by a stereoselective iridium(I)-catalyzed olefin isomerization. Natural cis-1 was preferentially degraded by HOCl and was more protective than trans-1 against lipid peroxidation induced by a free-radical initiator, demonstrating that the geometry of the 1'-alkenyloxy bond participates in the antioxidant defensive role of 1.