(2Z,5Z,8Z,11Z,14Z)-1-bromoheptadeca-2,5,8,11,14-pentaene | 1079399-59-9

• 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,14Z)-1-bromoheptadeca-2,5,8,11,14-pentaene
• 英文别名: (all-Z)-1-bromoheptadeca-2,5,8,11,14-pentaene
• CAS: 1079399-59-9
• 化学式: C₁₇H₂₅Br
• 分子量: 309.289
• InChiKey: DQIMCRUFEAMZOZ-JLNKQSITSA-N

物化性质

• 沸点：
  367.3±31.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (2Z,5Z,8Z,11Z,14Z)-1-bromoheptadeca-2,5,8,11,14-pentaene 、 12-(四氢-2H-吡喃-2-基氧基)-1-十二碳炔 在 乙基溴化镁 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以36%的产率得到2'-((all-Z)-nonacosa-14,17,20,23,26-pentaen-11-ynyloxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Odd-numbered very-long-chain polyunsaturated fatty acids from the dinoflagellate Amphidinium carterae identified by atmospheric pressure chemical ionization liquid chromatography–mass spectrometry

  摘要：

  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..

  DOI：

  10.1016/j.phytochem.2008.08.021
• 作为产物：
  描述：

  (2Z,5Z,8Z,11Z,14Z)-heptadeca-2,5,8,11,14-pentaen-1-ol 在 吡啶 、 溴 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以84%的产率得到(2Z,5Z,8Z,11Z,14Z)-1-bromoheptadeca-2,5,8,11,14-pentaene
  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

• METHODS FOR THE SYNTHESIS OF 13C LABELED PLASMALOGEN
  申请人：PHENOMENOME DISCOVERIES INC.

  公开号：US20140323749A1

  公开（公告）日：2014-10-30

  A method for preparing 13 C labeled plasmalogens as represented by Formula B: —The method involves producing a 13 C labeled cyclic plasmalogen precursor of Formula A, and conversion of the precursor to a plasmalogen of Formula B. These plasmalogens may potentially be useful in the determination of both the mechanism of action as well as the fate of plasmalogens in the body.

  一种制备以B式表示的13C标记的鞘磷脂的方法：该方法涉及生产A式的13C标记的环状鞘磷脂前体，并将前体转化为B式的鞘磷脂。这些鞘磷脂可能潜在地有助于确定鞘磷脂在体内的作用机制和命运。
• METHODS FOR THE SYNTHESIS OF 13C LABELED DHA AND USE AS A REFERENCE STANDARD
  申请人：PHENOMENOME DISCOVERIES INC.

  公开号：US20140336397A1

  公开（公告）日：2014-11-13

  A method for preparing 13 C labeled docosahexaenoic acid (DHA) represented by Formula A: The method comprises the conversion of 2-pentyn-1-ol to 13 C labeled DHA by reaction with propargyl alcohol, 13 C labeled propargyl alcohol and methyl pent-4-ynoate. The various steps involved include tosylation, coupling, bromination, selective hydrogenation and ester hydrolysis to obtain the final product.

  一种制备公式A所代表的13C标记的十二碳五烯酸（DHA）的方法：该方法包括将2-戊炔-1-醇与丙炔醇、13C标记的丙炔醇和甲基戊-4-炔酸酯反应，从而将其转化为13C标记的DHA。涉及的各个步骤包括磺酸化、偶联、溴化、选择性加氢和酯水解，以获得最终产品。
• US9006472B2
  申请人：——

  公开号：US9006472B2

  公开（公告）日：2015-04-14
• [EN] METHODS FOR THE SYNTHESIS OF 13C LABELED DHA AND USE AS A REFERENCE STANDARD<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE DHA MARQUÉ PAR 13C ET SON UTILISATION COMME ÉTALON DE RÉFÉRENCE
  申请人：PHENOMENOME DISCOVERIES INC

  公开号：WO2013071411A1

  公开（公告）日：2013-05-23

  A method for preparing 13C labeled docosahexaenoic acid (DHA) represented by Formula A: The method comprises the conversion of 2-pentyn-l-ol to 13C labeled DHA by reaction with propargyl alcohol, 13C labeled propargyl alcohol and methyl pent-4-ynoate. The various steps involved include tosylation, coupling, bromination, selective hydrogenation and ester hydrolysis to obtain the final product.
• 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..