(8Z)-heptadec-8-en-1-amine | 141903-93-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (8Z)-heptadec-8-en-1-amine
• 英文别名: (Z)-8-heptadecenylamine；cis-8-heptadecylamine；oleylamine；oleic acid；heptadec-8c-enylamine；Heptadec-8c-enylamin；(Z)-heptadec-8-en-1-amine
• CAS: 141903-93-7
• 化学式: C₁₇H₃₅N
• 分子量: 253.472
• InChiKey: HFMYCAZGBZLHCL-KTKRTIGZSA-N

物化性质

• 熔点：
  21 °C
• 沸点：
  147 °C(Press: 2 Torr)
• 密度：
  0.827±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (8Z)-heptadec-8-en-1-amine 在 四氮唑 、 双氧水 作用下， 生成 Phosphoric acid dibenzyl ester 2-[((Z)-3-heptadec-8-enyl)ureido]-ethyl ester
  参考文献：
  名称：

  轻松合成含有不饱和脂肪酸链的溶血磷脂

  摘要：

  由于不饱和部分对磷酸酯脱保护中所用条件的敏感性，有效合成多不饱和磷脂具有挑战性。我们在这里讨论三种独立的方法来解决此问题，并使一系列不饱和溶血磷脂酸模拟物的合成，以发展对该系列中结构-活性关系的更全面的了解。

  DOI：

  10.1016/0040-4039(96)01802-3
• 作为产物：
  描述：

  octadec-9(Z)-enoyl azide 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 45.0h， 生成 (8Z)-heptadec-8-en-1-amine
  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
• 作为试剂：
  描述：

  zinc diethyldithiocarbamate 、 copper diethyldithiocarbamate 、 tris(diethyldithiocarbamato)iron(III) 、 在 (8Z)-heptadec-8-en-1-amine 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis of Nanoparticulate Alloys of the Composition Cu₂Zn_1–xFe_xSnS₄: Structural, Optical, and Magnetic Properties

  摘要：

  Nanoparticles of the semiconductor Cu2Zn1-xFexSnS4 with different mole fractions of iron (x(Fe)) were synthesized by the decomposition of molecular precursors in oleylamine. The composition, structure, optical, and magnetic properties of the nanoparticles are reported. The parent (Cu2ZnSnS4) zinc material is usually reported as kesteritic and the corresponding iron phase as stannitic; with different site occupancies and tetragonalities. In the small ca. 8-10 nm particles prepared, the smooth variation in lattice parameters and other measured properties suggest that the phase change, with composition, may be absent. SQUID magnetometry suggests that the iron containing samples are ferromagnetic at 5 K and paramagnetic at 300 K.

  DOI：

  10.1021/jacs.5b10281

文献信息

• Vanilloids. 1. Analogs of capsaicin with antinociceptive and antiinflammatory activity
  作者：John M. Janusz、Brian L. Buckwalter、Patricia A. Young、Thomas R. LaHann、Ralph W. Farmer、Gerald B. Kasting、Maurice E. Loomans、Gary A. Kerckaert、Cherie S. Maddin

  DOI：10.1021/jm00070a002

  日期：1993.9

  As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion of the parent structure (and related compounds derived from homovanillic acid) was varied. In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures

  作为建立香草醛的结构活性关系的程序的一部分，辛辣成分辣椒素的类似物，母体结构的烷基链部分（以及衍生自高香草酸的相关化合物）发生了变化。在抗伤害感受和抗炎试验（大鼠和小鼠热板以及巴豆油刺激的小鼠耳朵）中，具有广泛变化的烷基链结构的化合物具有活性。短链化合物在上述测定中通过全身给药具有活性，但它们保留了辣椒素的高刺激性和急性毒性特征。相比之下，长链顺式不饱和物NE-19550（香草基油酰胺）和NE-28345（油基单香草酰胺）具有口服活性，刺激性较低，并且比辣椒素的急性毒性小。
• Pharmacological Characterization of Hydrolysis-Resistant Analogs of Oleoylethanolamide with Potent Anorexiant Properties
  作者：Giuseppe Astarita、Barbara Di Giacomo、Silvana Gaetani、Fariba Oveisi、Timothy R. Compton、Silvia Rivara、Giorgio Tarzia、Marco Mor、Daniele Piomelli

  DOI：10.1124/jpet.106.105221

  日期：2006.8

  Oleoylethanolamide (OEA) is an endogenous lipid mediator that reduces food intake, promotes lipolysis, and decreases body weight gain in rodents by activating peroxisome proliferator-activated receptor-α (PPAR-α). The biological effects of OEA are terminated by two intracellular lipid hydrolase enzymes, fatty-acid amide hydrolase and N -acylethanolamine-hydrolyzing acid amidase. In the present study, we describe OEA analogs that resist enzymatic hydrolysis, activate PPAR-α with high potency in vitro, and persistently reduce feeding when administered in vivo either parenterally or orally. The most potent of these compounds, ( Z )-( R )-9-octadecenamide, N -(2-hydroxyethyl,1-methyl) (KDS-5104), stimulates transcriptional activity of PPAR-α with a half-maximal effective concentration (EC50) of 100 ± 21 nM ( n = 11). Parenteral administration of KDS-5104 in rats produces persistent dose-dependent prolongation of feeding latency and postmeal interval (half-maximal effective dose, ED50 = 2.4 ± 1.8 mg kg-1 i.p.; n = 18), as well as increased and protracted tissue exposure compared with OEA. Oral administration of the compound also results in a significant tissue exposure and reduction of food intake in free-feeding rats. These results suggest that the endogenous high-affinity PPAR-α agonist OEA may provide a scaffold for the discovery of novel orally active PPAR-α ligands.

  油酰乙醇酰胺（OEA）是一种内源性脂质介质，可通过激活过氧化物酶体增殖激活受体-α（PPAR-α）来降低啮齿动物的食物摄入量、促进脂肪分解并减少体重增加。OEA 的生物效应由两种细胞内脂质水解酶（脂肪酸酰胺水解酶和 N -酰基乙醇胺水解酸酰胺酶）终止。在本研究中，我们描述了能抵抗酶水解的 OEA 类似物，它们能在体外高效力地激活 PPAR-α，并在体内经肠道或口服给药后持续减少摄食。这些化合物中效力最强的是 ( Z )-( R )-9- 十八烯酰胺，N -（2-羟乙基，1-甲基）（KDS-5104），它能刺激 PPAR-α 的转录活性，其半最大有效浓度（EC50）为 100 ± 21 nM（n = 11）。与 OEA 相比，KDS-5104 给大鼠肠外给药会产生持续的剂量依赖性进食潜伏期和餐后间隔延长（半数最大有效剂量，ED50 = 2.4 ± 1.8 mg kg-1 i.p.；n = 18），以及组织暴露增加和延长。在自由采食的大鼠中，口服该化合物也会导致显著的组织暴露和食物摄入量减少。这些结果表明，内源性高亲和力 PPAR-α 激动剂 OEA 可为发现新型口服活性 PPAR-α 配体提供支架。
• [EN] A NOVEL CATIONIC LIPID, A PREPARATION METHOD OF THE SAME AND A DELIVERY SYSTEM COMPRISING THE SAME<br/>[FR] NOUVEAU LIPIDE CATIONIQUE, PROCÉDÉ DE PRÉPARATION DE CE DERNIER ET SYSTÈME D'ADMINISTRATION LE COMPRENANT
  申请人：UNIV IND & ACAD COLLABORATION

  公开号：WO2009028824A3

  公开（公告）日：2009-04-23
• Highly active and long lived homogeneous catalyst for the dehydrogenation of dimethylamine borane starting with ruthenium(III) acetylacetonate and oleylamine precatalyst
  作者：Sibel Duman、Mehdi Masjedi、Saim Özkar

  DOI：10.1016/j.molcata.2015.08.006

  日期：2016.1

  Herein, we report the results of our study on the homogeneous catalytic dehydrogenation of dimethylamine borane in the presence of Ru(acac)(3) and oleylamine (OAm) in toluene solution. The precatalyst system comprising Ru(acac)(3) and 3 equivalent OAm shows the high catalytic activity in hydrogen generation from dimethylamine borane solution. Monitoring the hydrogen evolution shows the presence of an induction period during which the homogeneous catalyst is formed, and then the hydrogen evolution continues almost linearly until the complete dehydrogenation of dimethylamine borane. UV-vis spectroscopic observation implies on the formation of a ruthenium(II)species. Using UV-vis, FTIR, Mass, H-1 and C-13 NMR spectroscopies we could identify the presence of trans-[Ru(acac)(2)(OAm)(2)] in the solid residue obtained after the catalytic reaction. This complex might be a stable form of the active catalyst as it shows similar catalytic activity in dehydrogenation of dimethylamine borane as before. The precatalyst system comprising Ru(acac)(3) and 3 equivalent OAm provides 15,000 turnovers over 8 days with a constant turnover frequency of TOP = 77.8 h(-1) in hydrogen generation from the dehydrogenation of dimethylamine borane in toluene solution at 60.0 +/- 0.1 degrees C. Adding 3 equivalent OAm per Ru into the precatalyst solution increases the catalytic activity by a factor of similar to 5 and the lifetime of the catalyst by a factor of >9 compared to the ones obtained by using sole Ru(acac)(3). Kinetics of catalytic dehydrogenation of dimethylamine borane starting with Ru(acac)(3) and 3 equivalent OAm in toluene solution were studied depending on catalyst concentration, substrate concentration and temperature. The catalytic reaction was found to be first-order with respect to each of both Ru(acac)(3) and dimethylamine borane concentrations. The activation energy for the catalytic dehydrogenation is E-a = 58 +/- 2 kJ/mol. (C) 2015 Published by Elsevier B.V.
• Tulus, Istanbul Universitesi Fen Fakultesi Mecmuasi, Seri A: Matematik-Fizik-Kimya, 1950, vol. 15, p. 333,337
  作者：Tulus

  DOI：——

  日期：——