(E)-十八碳-4-烯酸 | 34450-19-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (E)-十八碳-4-烯酸
• 英文名称: (E)-octadec-4-enoic acid
• 英文别名: octadec-4t-enoic acid；Octadec-4t-ensaeure；Δ⁴-trans-Octadecensaeure；Octadec-trans-4-encarbonsaeure；trans-octadec-4-encarbonsaeure；trans-Octadecen-(4)-saeure；4-Octadecenoic acid
• CAS: 34450-19-6
• 化学式: C₁₈H₃₄O₂
• 分子量: 282.467
• InChiKey: OBNDIDKDLXSSCB-CCEZHUSRSA-N

物化性质

• 熔点：
  59.5-60.5 °C
• 沸点：
  400.1±14.0 °C(Predicted)
• 密度：
  0.899±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-十八碳-4-烯酸 在 吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Concise synthesis of (+)-serinolamide A

  摘要：

  Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from L-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.084
• 作为产物：
  描述：

  (S)-5-((R)-1-Hydroxy-tetradecyl)-dihydro-furan-2-one 在 硫酸 、 氢溴酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 生成 (E)-十八碳-4-烯酸
  参考文献：
  名称：

  1121.长链酸的合成。第五部分。某些ω-羟基乙炔酸的合成

  摘要：

  DOI：

  10.1039/jr9630005889

文献信息

• FUNCTIONALIZED MONOMERS AND POLYMERS
  申请人：DiBiase Stephen Augustine

  公开号：US20120245063A1

  公开（公告）日：2012-09-27

  This invention relates to a composition, comprising: an unsaturated functionalized monomer of from about 5 to about 30 carbon atoms, which is: (a) polymerized to form a functionalized polymer; (b) copolymerized with a comonomer to form a functionalized copolymer; or (c) reacted with an enophilic reagent to form a polyfunctionalized monomer. The polyfunctionalized monomer may be polymerized to form a polyfunctionalized polymer which may be further reacted with one or more additional reagents. The invention relates to lubricants, functional fluids, fuels, dispersants, detergents and polymeric resins.

  这项发明涉及一种组合物，包括：一个由约5至约30个碳原子的不饱和官能化单体组成，该单体：(a)聚合形成官能化聚合物；(b)与共聚单体共聚形成官能化共聚物；或(c)与亲亚烯试剂反应形成多官能单体。多官能单体可以聚合形成多官能聚合物，该聚合物可以进一步与一个或多个额外试剂反应。该发明涉及润滑剂、功能流体、燃料、分散剂、清洁剂和聚合树脂。
• Enantioselective total synthesis of (+)-serinolamide A
  作者：Suraksha Gahalawat、Satyendra Kumar Pandey

  DOI：10.1039/c5ra06609c

  日期：——

  A short and highly efficient enantioselective synthetic approach to (+)-serinolamide A 1 from racemic butadiene monoepoxide as a starting material is described. The synthesis utilizes the palladium catalyzed Trost's Dynamic Kinetic Asymmetric Transformation (DYKAT) and cross-metathesis (CM) as key steps.

  描述了一种由外消旋的丁二烯单环氧化物作为起始原料制备（+）-丝氨酰胺A 1的短而高效的对映选择性合成方法。该合成利用钯催化的Trost的动态动力学不对称转化（DYKAT）和交叉复分解（CM）作为关键步骤。
• Synthesis and Evaluation of Serinolamide Derivatives as Sphingosine-1-Phosphate-1 (S1P1) Receptor Agonists
  作者：Sun Jun Park、Jushin Kim、Jaehwan Kim、Yoowon Kim、Elijah Hwejin Lee、Hyeon Jeong Kim、Siwon Kim、Byungeun Kim、Rium Kim、Ji Won Choi、Jong-Hyun Park、Ki Duk Park

  DOI：10.3390/molecules27092818

  日期：——

  Sphingosine-1-phosphate-1 (S1P1) receptor agonists are well-known drugs for treating multiple sclerosis (MS) caused by autoreactive lymphocytes that attack the myelin sheath. Therefore, an effective therapeutic strategy is to reduce the lymphocytes in the blood by inducing S1P1 receptor internalization. We synthesized serinolamide A, a natural product of the sea, and performed S1P1 receptor internalization assay to evaluate functionally antagonistic S1P1 receptor agonist activity. In order to synthesize derivatives with better efficacy than serinolamide A and B, new derivatives were synthesized by introducing the phenyl ring moiety of fingolimod. Among them, compounds 19 and 21 had superior S1P1 agonistic effects to serinolamide. We also confirmed that compound 19 effectively inhibited lymphocyte outflow in peripheral lymphocyte count (PLC) assay.

  Sphingosine-1-phosphate-1 (S1P1) 受体激动剂是治疗由自身免疫淋巴细胞攻击髓鞘引起的多发性硬化症（MS）的常用药物。因此，一种有效的治疗策略是通过诱导 S1P1 受体内化来减少血液中的淋巴细胞。我们合成了海洋天然产物丝氨酰胺A，并进行了 S1P1 受体内化试验，评估其功能上的拮抗 S1P1 受体激动剂活性。为了合成比丝氨酰胺A和B更有效的衍生物，我们通过引入芬格莫德的苯环基团，合成了新的衍生物。其中，化合物19和21具有比丝氨酰胺更优异的S1P1激动作用。我们还确认，化合物19有效地抑制了外周淋巴细胞计数（PLC）试验中的淋巴细胞外流。
• MALIENATED DERIVATIVES
  申请人：DiBiase Stephen A.

  公开号：US20120264664A1

  公开（公告）日：2012-10-18

  This invention relates to malienated derivatives made from maleic anhydride, functionalized monomers, and one or more additional reagents, e.g., an oxygen-containing reagent (e.g., alcohol, polyol), a nitrogen-containing reagent (e.g., amine, polyamine, aminoalcohol), a metal and/or a metal compound. The invention relates to lubricants, functional fluids, fuels, dispersants, detergents and functional compositions (e.g., cleaning solutions, food compositions, etc.)

  本发明涉及由马来酸酐、官能化单体和一个或多个附加试剂制成的马来化衍生物，例如含氧试剂（例如醇，多元醇），含氮试剂（例如胺，多胺，氨基醇），金属和/或金属化合物。本发明涉及润滑剂、功能液体、燃料、分散剂、清洁剂和功能组合物（例如清洁溶液、食品组合物等）。
• FUNCTIONALIZED MONOMERS
  申请人：DiBiase Stephen A.

  公开号：US20120283156A1

  公开（公告）日：2012-11-08

  This invention relates to functionalized monomers which are reacted with an enophilic reagent (e.g., maleic anhydride) to form an enophilic reagent modified functionalized monomer. The enophilic reagent modified functionalized monomer may be further reacted with one or more additional reagents (e.g., oxygen-containing reagents, nitrogen-containing reagents, metals or metal compounds). The invention relates to base oils which may comprise functional base oils. The invention relates to lubricants, functional fluids, fuels, dispersants, detergents and functional compositions (e.g., cleaning solutions, food products, etc.).

  本发明涉及功能化单体，其与亲亚烯试剂（例如马来酸酐）反应，形成亲亚烯试剂修饰的功能化单体。亲亚烯试剂修饰的功能化单体可以进一步与一个或多个其他试剂（例如含氧试剂、含氮试剂、金属或金属化合物）反应。本发明涉及可能包括功能基础油的基础油。本发明涉及润滑剂、功能性流体、燃料、分散剂、清洁剂和功能性组合物（例如清洁溶液、食品产品等）。