(2Z,5Z,8Z,11Z)-1-bromoheptadeca-2,5,8,11-tetraene | 1079399-60-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: (2Z,5Z,8Z,11Z)-1-bromoheptadeca-2,5,8,11-tetraene
• 英文别名: (all-Z)-1-bromoheptadeca-2,5,8,11-tetraene
• CAS: 1079399-60-2
• 化学式: C₁₇H₂₇Br
• 分子量: 311.305
• InChiKey: WACVXUPBMDVXNH-DOFZRALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  18.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (2Z,5Z,8Z,11Z)-1-bromoheptadeca-2,5,8,11-tetraene 、 2-(nonadeca-12,15,18-triynyloxy)tetrahydro-2H-pyran 在 乙基溴化镁 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 12.17h， 生成
  参考文献：
  名称：

  Identification of very-long-chain polyunsaturated fatty acids from Amphidinium carterae by atmospheric pressure chemical ionization liquid chromatography–mass spectroscopy

  摘要：

  A method is described for the enrichment of very-long-chain polyunsaturated fatty acids (VLCPUFAs) from total fatty acids of Amphidinium carterae and their identification as picolinyl esters by means of microbore liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization (LC-MS/APCI). The combination of argentation TLC and LC-MS/APCI was used to identify unusual VLCPUFAs up to hexatriacontaoctaenoic acid. Two acids, 36:7n-6 and 36:8n-3, were also synthesized to unambiguously confirm their structure. The possibilities of VLCPUFAs biosynthesis are proposed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.06.011
• 作为产物：
  描述：

  (2Z,5Z,8Z,11Z)-heptadeca-2,5,8,11-tetraen-1-ol 在 吡啶 、 溴 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以86%的产率得到(2Z,5Z,8Z,11Z)-1-bromoheptadeca-2,5,8,11-tetraene
  参考文献：
  名称：

  Identification of very-long-chain polyunsaturated fatty acids from Amphidinium carterae by atmospheric pressure chemical ionization liquid chromatography–mass spectroscopy

  摘要：

  A method is described for the enrichment of very-long-chain polyunsaturated fatty acids (VLCPUFAs) from total fatty acids of Amphidinium carterae and their identification as picolinyl esters by means of microbore liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization (LC-MS/APCI). The combination of argentation TLC and LC-MS/APCI was used to identify unusual VLCPUFAs up to hexatriacontaoctaenoic acid. Two acids, 36:7n-6 and 36:8n-3, were also synthesized to unambiguously confirm their structure. The possibilities of VLCPUFAs biosynthesis are proposed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.06.011

文献信息

• Odd-numbered very-long-chain polyunsaturated fatty acids from the dinoflagellate Amphidinium carterae identified by atmospheric pressure chemical ionization liquid chromatography–mass spectrometry
  作者：Tomáš Řezanka、Linda Nedbalová、Karel Sigler

  DOI：10.1016/j.phytochem.2008.08.021

  日期：2008.11

  A method is described for the enrichment of odd very-long-chain polyunsaturated fatty acids (VLCPUFAs) by means of RP-HPLC and argentation TLC from total fatty acids of the dinoflagellate A. carterae and their identification as picolinyl esters by means of microbore liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization (LC-MS/APCI). The combination of argentation TLC and LC-MS/ APCI was used to identify rare and unusual odd VLCPUFAs up to nonacosahexaenoic acid. Two acids, (allZ)-nonacosa-11,14,17,20,23-pentaenoic acid (29:5n-6) and (allZ)-nonacosa-11,14,17,20,23,26-hexaenoic acid (29:6n-3), were synthesized for the first time to unambiguously confirm their structure. Possible biosynthetic pathways for odd VLCPUFAs are also proposed. All rights reserved (C) 2008 Elsevier Ltd..