13-hydroxytrideca-5,8,11-triynoic acid methyl ester | 741675-40-1

• 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: 13-hydroxytrideca-5,8,11-triynoic acid methyl ester
• 英文别名: methyl 13-hydroxytrideca-5,8,11-triynoate；13-hydroxy-trideca-5,8,11-triynoic acid methyl ester
• CAS: 741675-40-1
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: YFUSJPBLRYHHJR-UHFFFAOYSA-N

物化性质

• 沸点：
  387.7±42.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  13-hydroxytrideca-5,8,11-triynoic acid methyl ester 在 lithium hydroxide 、 copper(l) iodide 、 四溴化碳 、 nickel boride (P-2 Ni) 、 氢气 、 potassium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 (5Z,8Z,11Z,14Z)-21-Chloro-henicosa-5,8,11,14-tetraen-17-ynoic acid
  参考文献：
  名称：

  A synthetic route to anandamide analogues carrying a substituent at the terminal carbon and an acetylene group in the end pentyl chain

  摘要：

  A versatile sequence is developed for the synthesis of' anandamide analogues with an acetylene group in the end pentyl chain carrying a substituent at the terminal carbon of the chain. These analogues are important for SAR studies of the endocannabinoid. anandamide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.071
• 作为产物：
  描述：

  5-己炔酸甲酯 在 copper(l) iodide 、 三溴化磷 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.0h， 生成 13-hydroxytrideca-5,8,11-triynoic acid methyl ester
  参考文献：
  名称：

  Synthesis and functional pharmacological effects on human bronchi of 20-hydroxyeicosatetraenoic acid

  摘要：

  我们通过一种新路线合成了20-羟基二十烷四烯酸（20-HETE），并阐明了其在人体支气管中的功能效应。进行了等张张力测量，结果表明合成的20-HETE对休息张力和用美托啶预收缩的支气管产生了浓度依赖的松弛效应。

  DOI：

  10.1007/s10600-011-9765-z

文献信息

• Reaction of 1-Trimethylsilyl-1,2-epoxy-3-alkanols with Alkynes and Application to the Synthesis of 18-HEPE
  作者：Yuichi Kobayashi、Yutaro Nanba、Masao Morita

  DOI：10.1055/s-0037-1610194

  日期：2018.8

  (E)-TMS-C≡C-CH=CHCH(OH)R. The (E) stereo­chemistry was independent of the anti/syn stereochemistry, but the syn isomers showed higher reactivity than the anti isomers. The reaction was applied to the synthesis of (18R)- and (18S)-HEPE.

  衍生自 (E)-TMS-CH=CHCH(OH)R 的环氧醇（反和/或顺异构体）与 TMS-C≡CLi 在 THF/HMPA 中立体选择性地得到 (E)-TMS-C≡C- CH=CHCH(OH)R。(E) 立体化学独立于反/顺式立体化学，但顺式异构体显示出比反异构体更高的反应性。该反应用于合成(18R)-和(18S)-HEPE。
• Fluorogenic probes to monitor cytosolic phospholipase A₂ activity
  作者：Cheng Yang Ng、Timothy Xiong Wei Kwok、Francis Chee Kuan Tan、Chian-Ming Low、Yulin Lam

  DOI：10.1039/c6cc09305a

  日期：——

  Arachidonic acid derivatives equipped with either one or two fluorescent groups attached to the tip of the alkyl chains were synthesized and shown to function as inhibitor and substrate probes...

  合成了带有一个或两个连接在烷基链末端的荧光基团的花生四烯酸衍生物，并显示出其作为抑制剂和底物探针的功能。
• [EN] MACROCYCLIC TRIENE LACTONES HAVING UNCONJUGATED TRIENE STRUCTURE, ITS PRODUCTION METHOD AND ITS SYNTHETIC INTERMEDIATE<br/>[FR] LACTONES TRIÉNIQUES MACROCYCLIQUES AYANT UNE STRUCTURE TRIÉNIQUE NON CONJUGUÉE, SON PROCÉDÉ DE PRODUCTION ET SON INTERMÉDIAIRE DE SYNTHÈSE
  申请人：TAKASAGO PERFUMERY CO LTD

  公开号：WO2012115285A1

  公开（公告）日：2012-08-30

  The present invention provides a novel macrocyclic compound exhibiting superior odor qualities and having a musk-like aroma, a method for producing the same, and a novel flavor or fragrance composition, and food products or beverages, fragrances or cosmetics, daily necessities or household goods and oral products using the novel macrocyclic compound. The invention relates to a compound represented by the formula (1), wherein each of wavy lines represents at least one of an E-configuration of C=C double bond and an Z-configuration of C=C double bond; m represents an integer of 0 to 10; and n represents an integer of 1 to 11, and n represents an integer of 1 to 11 when m is 0 to 4 or 6 to 10, and n is an integer of 1or 3 to 11 when m is 5.

  本发明提供了一种新型的大环化合物，具有优异的气味特性和麝香般的香气，以及制备该化合物的方法和一种新型的风味或香料组合物，以及使用该新型大环化合物的食品或饮料、香水或化妆品、日用品或家居用品和口腔产品。该发明涉及一种由式（1）表示的化合物，其中波浪线表示C=C双键的E构型和Z构型中的至少一个；m表示0到10的整数；n表示1到11的整数，当m为0到4或6到10时，n表示1到11的整数，当m为5时，n表示1或3到11的整数。
• MACROCYCLIC TRIENE LACTONES HAVING UNCONJUGATED TRIENE STRUCTURE, ITS PRODUCTION METHOD AND ITS SYNTHETIC INTERMEDIATE
  申请人：TAKASAGO INTERNATIONAL CORPORATION

  公开号：US20150266847A1

  公开（公告）日：2015-09-24

  The present invention provides a novel macrocyclic compound exhibiting superior odor qualities and having a musk-like aroma, a method for producing the same, and a novel flavor or fragrance composition, and food products or beverages, fragrances or cosmetics, daily necessities or household goods and oral products using the novel macrocyclic compound. The invention relates to a compound represented by the formula (1), wherein each of wavy lines represents at least one of an E-configuration of C═C double bond and an Z-configuration of C═C double bond; m represents an integer of 0 to 10; and n represents an integer of 1 to 11, and n represents an integer of 1 to 11 when m is 0 to 4 or 6 to 10, and n is an integer of 1 or 3 to 11 when m is 5.

  本发明提供了一种新型大环化合物，具有卓越的气味特性和麝香般的香气，以及其制备方法、新型风味或香料组合物、食品或饮料、香料或化妆品、日用品或家居用品和口腔产品，其中所述大环化合物的化学式为（1），其中波浪线表示C═C双键的E构型和Z构型中的至少一个；m表示0到10的整数；n表示1到11的整数，当m为0到4或6到10时，n表示1到11的整数，当m为5时，n表示1或3到11的整数。
• High Affinity Electrophilic and Photoactivatable Covalent Endocannabinoid Probes for the CB1 Receptor
  作者：Chen Li、Wei Xu、Subramanian K. Vadivel、Pusheng Fan、Alexandros Makriyannis

  DOI：10.1021/jm050272i

  日期：2005.10.1

  We have designed and synthesized the first two high affinity covalent anandamide probes for the CB1 receptor by introducing either an electrophilic isothiocyanato or a photoactivatable azido group at the terminal carbon of the arachidonic acid moiety. The headgroup of these anandamide analogues was optimized by using a cyclopropylamide substituent to impart optimal CB1 affinity. Both 20-isothiocyanato-eicosa-5,8,11,14-tetraenoic acid cyclopropylamide (1, AM3677) and 20-azido-eicosa-5,8,11,14-tetraenoic acid cyclopropylamide (2, AM3661) exhibited high selectivities for the CB 1 receptor with K-i values of 1.3 and 0.9 nM, respectively. Using suitable experimental conditions, both ligands were shown to covalently label the CB1 receptor with high efficiency. These two covalent probes for the endocannabinoid CB1 binding site open the door for exploring the ligand binding motifs involved in the activation of the CB1 receptor by its endogenous ligand, anandamide.