15-((tetrahydro-2H-pyran-2-yl)oxy)pentadecan-1-ol | 427901-46-0

• 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: 15-((tetrahydro-2H-pyran-2-yl)oxy)pentadecan-1-ol
• 英文别名: 15-(Oxan-2-yloxy)pentadecan-1-ol；15-(oxan-2-yloxy)pentadecan-1-ol
• CAS: 427901-46-0
• 化学式: C₂₀H₄₀O₃
• 分子量: 328.536
• InChiKey: UUHQMDICCVLQFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  15-((tetrahydro-2H-pyran-2-yl)oxy)pentadecan-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到2-((15-bromopentadecyl)-oxy)-tetrahydro-2H-pyran
  参考文献：
  名称：

  一些非典型鞘氨醇碱基的合成与表征

  摘要：

  鞘脂是所有真核生物和某些原核生物中普遍存在的丰富组成部分。鞘脂不仅在不同物种之间而且在单个细胞内都显示出很大的结构多样性。该品种不仅限于例如鞘糖脂的极性头基的改变，而且一方面影响由不同脂肪酸组成的亲脂性锚，另一方面影响由不同鞘氨醇碱基组成的亲脂性锚。例如在病原体中的不同鞘氨醇碱基内的结构变异可用于鉴定新的生物标志物和药物靶标，并且常见和不常见鞘脂的概况的特定变化与诸如糖尿病或癌症的病理状况相关。所以，鞘脂血症的新兴领域致力于收集细胞鞘脂组的数据，从而将其中的变化分配给细胞的某些状态或病理状况。但是，这种强大的工具仍然受到有关单个脂质种类的结构信息的可用性以及适用于定量的内部标准的限制。在本文中，我们描述了各种1-脱氧-鞘氨醇碱的合成。1-脱氧鞘脂由于其在罕见的遗传性神经病HSAN1中的病理作用，而且还作为II型糖尿病的预测性生物标志物，最近获得了广泛的关注。已经使用了本文合成和表征的某些化

  DOI：

  10.1016/j.bmc.2018.06.031
• 作为产物：
  描述：

  环十五内酯 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 、 糠酸莫米松水合物 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 15-((tetrahydro-2H-pyran-2-yl)oxy)pentadecan-1-ol
  参考文献：
  名称：

  具有全氘化和特别是ω氘化N-酰基残基的神经酰胺NS和NP的合成

  摘要：

  描述了 12 种氘化神经酰胺的合成，它们在酰胺结合的脂肪酸的最后一个碳原子上有一个氘化，或者是一个全氘化的脂肪酸链。神经酰胺是从鞘氨醇或植物鞘氨醇和ω 氘化或全氘化脂肪酸以 PyBOP® 作为活化剂以高产率制备的。为了合成特定的氘代脂肪酸，二元羧酸被转化为 ω 氘代烷基溴，通过铜催化的格氏偶联，用封闭的 ω 溴醇将其链延长。再生醇功能的氧化产生ω氘代脂肪酸。

  DOI：

  10.1002/jlcr.3443

文献信息

• NOVEL CYP-EICOSANOID DERIVATIVES
  申请人：MAX-DELBRÜCK-CENTRUM FÜR MOLEKULARE MEDIZIN

  公开号：US20170008918A1

  公开（公告）日：2017-01-12

  The present invention relates to compounds according to general formula (I) which are analogues of epoxymetabolites produced by cytochrome P450 (CYP) enzymes from omega-3 (n-3) polyunsaturated fatty acids (PUFAs). The present invention further relates to compositions containing one or more of these compounds and to the use of these compounds or compositions for C the treatment or prevention of conditions and diseases associated with inflammation, proliferation, hypertension, coagulation, immune function, pathologic angiogenesis, heart failure and cardiac arrhythmias.

  本发明涉及一般式（I）的化合物，这些化合物是由细胞色素P450（CYP）酶从ω-3（n-3）多不饱和脂肪酸（PUFAs）产生的环氧代谢产物的类似物。本发明还涉及含有这些化合物中的一个或多个的组合物，以及利用这些化合物或组合物用于治疗或预防与炎症、增殖、高血压、凝血、免疫功能、病理性血管生成、心力衰竭和心律失常相关的疾病和症状。
• Mycobacterium alvei (ω-1)-methoxy mycolic acids: Absolute stereochemistry and synthesis
  作者：Zamzam S. Alhuwaymil、Intisar Q.M. Al-araj、Ahmad R. Al Dulayymi、Alison Jones、Paul J. Gates、Pedro L. Valero-Guillén、Mark S. Baird、Juma’a R. Al Dulayymi

  DOI：10.1016/j.chemphyslip.2020.104977

  日期：2020.11

  various enzymes in the biosynthesis of other types of mycolic acid have been widely studied, the biosynthetic route to this substituent is unclear. We now define the stereochemistry of the (ω-1)-methoxy fragment as R, and describe the synthesis of a major R-(ω-1)-methoxy-mycolic acid and its sugar esters, and of two natural M. alvei diene mycolic acids.

  已知肺分枝杆菌细胞含有一组独特的带有 (ω-1)-甲氧基的分枝杆菌酸；尽管已经广泛研究了其他类型霉菌酸生物合成中的各种酶，但该取代基的生物合成途径尚不清楚。我们现在将 (ω-1)-甲氧基片段的立体化学定义为R，并描述主要的R- (ω-1)-甲氧基分枝杆菌酸及其糖酯的合成，以及两种天然M. alvei二烯的合成霉菌酸。
• 10.1016/j.tet.2024.134069
  作者：Mahajan, Prashant、Rode, Suryakant R.、Thakur, Ravi、Shirsath, Mahesh K.、Dadhaniya, Bhavik、Doss, Rajesh、Khan, Nadeem A.

  DOI：10.1016/j.tet.2024.134069

  日期：——

  ways to synthesize fatty acids, the chemical synthesis route offers more advantages in terms of versatility and targeted synthesis. Though remarkable achievements have been made in the field of fatty acid synthesis, it is still in the preliminary stage of optimization. In this paper, we wish to report a more practical & scalable approach for the synthesis of fatty acids with carbon atoms ranging from

  植物和动物来源的脂肪酸是化学工业的重要可再生原料。在过去的二十年里，它们的应用增加了数倍。虽然合成脂肪酸的方法有很多种，但化学合成路线在通用性和合成目标方面更具优势。尽管脂肪酸合成领域已经取得了显著成果，但仍处于初步优化阶段。在本文中，我们希望报告一种更实用且可扩展的合成碳原子数为 20 至 45 的脂肪酸的方法。
• ——
  作者：Robert J. Bartelt、Allard A. Cossé、Richard J. Petroski、David K. Weaver

  DOI：10.1023/a:1017994410538

  日期：——

  The cuticular lipids of the wheat stem sawfly Cephus cinctus (Hymenoptera: Cephidae) were investigated as part of a chemical ecology project with this species. The major cuticular lipids were n-alkenes and n-alkanes. Alkenes were the most abundant and exhibited dramatic sexual dimorphism. (Z)-9-Tricosene accounted for about half of the total hydrocarbon in males but was nearly absent from females. The dominant alkenes in females were (Z)-9-pentacosene and (Z)-9-heptacosene. The alkane profiles were similar in both sexes, with n-tricosane being the most abundant, followed by n-pentacosane and n-heptacosane. In both sexes, there were minor amounts of alkanes and alkenes with other chain lengths and n-alkadienes of 29 and 31 carbons. In males, about one tenth of the surface lipids consisted of (Z)-9-alkene-1, omega-diol diacetates with 22-, 24-, and 26-carbon chains. The same compounds were also detected from females but in much smaller amounts. The structures of these novel diacetates were proven by synthesis. By analogy to methyl oleate, a well-studied food lipid, the alkenes and diacetates were expected to undergo slow oxidation in air to release specific aldehydes and other volatile products, and these were generally detected in volatiles collected from living sawflies. Atmospheric oxidation of the diacetates was also demonstrated in the absence of sawflies. One product from the diacetates, 9-acetyloxynonanal, was shown in other research to be particularly active electrophysiologically and was also attractive in the field. Aldehydes from the alkenes also showed strong electrophysiological activity. The concept of volatile pheromones originating from heavy, unsaturated cuticular lipids is discussed.
• Z-Selective intramolecular Horner–Wadsworth–Emmons reaction for the synthesis of macrocyclic alkenes
  作者：Kaori Ando、Kaori Sato

  DOI：10.1016/j.tetlet.2011.01.043

  日期：2011.3

  The Z-selective intramolecular Horner-Wadsworth-Emmons reaction of the substrates 7-12 (RO)(2)P(O)CHR'CO(2)Et (R' = (CH(2))(n)CHO) (R = Ph or o-tBuC(6)H(4)) gives the 13-18-membered cyclic alkenes selectively (up to Z:E = 97:3) in good yields using NaH in THF under high dilution conditions. (C) 2011 Elsevier Ltd. All rights reserved.