methyl (9Z)-12-bromododec-9-enoate | 186797-96-6

• 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: methyl (9Z)-12-bromododec-9-enoate
• 英文别名: methyl (Z)-12-bromododec-9-enoate
• CAS: 186797-96-6
• 化学式: C₁₃H₂₃BrO₂
• 分子量: 291.228
• InChiKey: RUNQNQZKQXDHPM-VURMDHGXSA-N

物化性质

• 沸点：
  333.1±25.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  methyl (9Z)-12-bromododec-9-enoate 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 16.0h， 生成 (9Z)-12-[4-[(E)-phenyldiazenyl]phenoxy]dodec-9-enoic acid
  参考文献：
  名称：

  Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials

  摘要：

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.

  DOI：

  10.1021/jo301659c
• 作为产物：
  描述：

  12-(四氢-2H-吡喃-2-基氧基)-3-十二碳炔-1-醇 在 Lindlar's catalyst 、 增效醚 吡啶 、 jones reagent 、 四溴化碳 、 氢气 、 乙酰氯 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.17h， 生成 methyl (9Z)-12-bromododec-9-enoate
  参考文献：
  名称：

  与脂肪酸去饱和有关的研究，III。硫代酸的制备和使用†

  摘要：

  已经制备了新的硫代酸甲酯1作为用于研究Δ12饱和的模型，描述了从10-（四氢吡喃基氧基）-dec-1-yne 2到那些酸的聚合合成途径。皂化后，在[1-的体内去饱和的抑制作用14 C]油酸到[1- 14 C]亚油酸已经利用绿藻类，评估小球藻sorokiniana，作为生物模型。该结果可能表明油基去饱和酶通过在C-13上夺氢原子而引发正常底物的脱氢。

  DOI：

  10.1002/jlac.199719970108

文献信息

• Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials
  作者：Yazmin M. Osornio、Peter Uebelhart、Silvan Bosshard、Fabian Konrad、Jay S. Siegel、Ehud M. Landau

  DOI：10.1021/jo301659c

  日期：2012.12.7

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.
• Studies Related to Fatty Acid Desaturation, III. Preparation and Use of Thiaoleic Acids
  作者：S. Poulain、N. Noiret、C. Nugier-Chauvin、H. Patin

  DOI：10.1002/jlac.199719970108

  日期：1997.1

  New thiaoleic acid methyl esters 1 have been prepared as models for studies on Δ12-saturation, Convergent synthetic pathways to those acids from the 10-(tetrahydropyranyloxy)-dec-1-yne 2 are described. After saponification, their inhibitory effect on the in vivo desaturation of [1-14C] oleic acid into [1-14C] linoleic acid has been evaluated using green algae, Chlorella sorokiniana, as a biological

  已经制备了新的硫代酸甲酯1作为用于研究Δ12饱和的模型，描述了从10-（四氢吡喃基氧基）-dec-1-yne 2到那些酸的聚合合成途径。皂化后，在[1-的体内去饱和的抑制作用14 C]油酸到[1- 14 C]亚油酸已经利用绿藻类，评估小球藻sorokiniana，作为生物模型。该结果可能表明油基去饱和酶通过在C-13上夺氢原子而引发正常底物的脱氢。