methyl (9Z,12R)-12-{[tert-butyl(dimethyl)silyl]oxy}octadec-9-enoate | 129049-75-8

• 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,12R)-12-{[tert-butyl(dimethyl)silyl]oxy}octadec-9-enoate
• 英文别名: methyl (12R)-[(tert-butyldimethylsilyl)oxy]octadec-(9Z)-enoate；(12R,9Z)-methyl 12-[(tert-butyldimethylsilyl)oxy]octadec-9-enoate；methyl (R,Z)-12-((tert-butyldimethylsilyl)oxy)octadec-9-enoate；methyl (Z,12R)-12-[tert-butyl(dimethyl)silyl]oxyoctadec-9-enoate
• CAS: 129049-75-8
• 化学式: C₂₅H₅₀O₃Si
• 分子量: 426.756
• InChiKey: PKRCQALSNKJWRO-NTOIIUQRSA-N

物化性质

• 沸点：
  457.5±28.0 °C(Predicted)
• 密度：
  0.887±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (9Z,12R)-12-{[tert-butyl(dimethyl)silyl]oxy}octadec-9-enoate 在 lithium aluminium tetrahydride 、 lithium cyclohexylisopropylamide 、 对甲苯磺酸 、 甲基磺酰氯 、 三乙胺 、 lithium bromide 作用下， 以 乙醚 为溶剂， 反应 35.33h， 生成 羟基二十碳烯酸甲酯
  参考文献：
  名称：

  Configurational purity of lesquerolic acid

  摘要：

  摘要用(S)-1-(1′-萘基)乙基异氰酸酯将(R)-14-羟基-Z-11-二十烯酸甲酯转化为氨基甲酸酯，得到单一非对映异构体。比较从外消旋酯和从蓖麻油酸合成的(R)-12-羟基-Z-9-十八烯酸样品中获得的相关非对映异构体的洗脱顺序，结果与最初确定的长链酸的(R)构型一致。尽管构型并不存在疑问，但这项工作证明了女贞子酸的构型纯度。

  DOI：

  10.1007/bf02660724
• 作为产物：
  描述：

  蓖麻油酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼 作用下， 反应 72.33h， 生成 methyl (9Z,12R)-12-{[tert-butyl(dimethyl)silyl]oxy}octadec-9-enoate
  参考文献：
  名称：

  Properties of unusual phospholipids. III: Synthesis, monolayer investigations and DSC studies of hydroxy octadeca(e)noic acids and diacylglycerophosphocholines derived therefrom

  摘要：

  Diacylglycerophosphocholines containing (R)-3-, (R)-12-, (R)-17-hydroxy octadeca(e)noic acids and the corresponding racemates were synthesized and purified to homogeneity. The influence of the position of the hydroxy group on the monolayer packing properties of these fatty acids and their phosphatidylcholines was studied by Langmuir techniques and 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine displayed the largest lift-off area (330 Angstrom(2)/molecule). This result was in line with the thermotropic phase behavior of these phospholipids, as measured by differential scanning calorimetry (DSC): the gel-to liquid-crystalline phase transition temperature (T-m) passed through a minimum of -15.1 degrees C for 1,2-di-[(R)-12-hydroxy-octadec-cis-9-enyl]-sn-glycero-3-phosphocholine. (C) 1997 Elsevier Science Ireland Ltd.

  DOI：

  10.1016/s0009-3084(97)00085-6

文献信息

• Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists
  作者：Aniello Schiano Moriello、Silvia López Chinarro、Olalla Novo Fernández、Jordi Eras、Pietro Amodeo、Ramon Canela-Garayoa、Rosa Maria Vitale、Vincenzo Di Marzo、Luciano De Petrocellis

  DOI：10.1021/acs.jmedchem.8b00734

  日期：2018.9.27

  potent pharmacological tools and endogenous modulators. Here we describe the discovery of novel synthetic long-chain capsaicin derivatives as potent TRPV2 antagonists in comparison to the totally inactive capsaicin, the role of their hydrophobic chain, and how the structure–activity relationships of such derivatives led, through a ligand-based approach, to the identification of endogenous long-chain

  瞬时受体电位香草2型（TRPV2）蛋白是非选择性Ca 2+由于缺乏可用的选择性和有效的药理学工具和内源性调节剂，TRPV亚家族的可渗透通道成员仍被认为是孤立的TRP通道。在这里，我们描述了通过完全基于配体的方法发现的新型合成长链辣椒素衍生物作为强效TRPV2拮抗剂（与完全无活性的辣椒素相比），它们的疏水链的作用以及这些衍生物的结构-活性关系如何导致的发现。 ，以鉴定充当TRPV2拮抗剂的内源性长链脂肪酸乙醇酰胺或伯酰胺。合成的和内源性的拮抗剂都表现出对以不同的动力学特征为特征的已知TRPV2激动剂的不同抑制作用。
• Synthesis of Phosphatidylcholines Possessing Functionalized Acids at sn-2, and 13C–14N and 13C–31P Couplings in Their 13C NMR Spectra
  作者：Masao Morita、Shun Saito、Riku Shinohara、Ryohei Aoyagi、Makoto Arita、Yuichi Kobayashi

  DOI：10.1055/s-0039-1691584

  日期：2020.4

  N-methylimidazole (NMI) was examined for the condensation of acids with 1-stearoyl-lysophosphatidylcholine because of the non-tailing nature of NMI on silica gel. Acids tested were EPA, α-linolenic acid, TBS ethers of 18-HEPE and ricinoleic acid, acid-labile epoxy acids, and a phenyldiynyl acid. The condensation proceeded well with these acids, and chromatographic separation of resulting phosphatidylcholines

  尽管 4-Me2NC5H4N (DMAP) 是 (2-Me-​​6-NO2-C6H3CO)2O (MNBA) 酯化的标准碱，但研究了 N-甲基咪唑 (NMI) 与 1-硬脂酰-溶血磷脂酰胆碱的酸缩合反应，因为NMI 在硅胶上的无拖尾特性。测试的酸是 EPA、α-亚麻酸、18-HEPE 和蓖麻油酸的 TBS 醚、酸不稳定环氧酸和苯基二炔酸。这些酸的缩合进行得很好，并且很容易对所得的磷脂酰胆碱和剩余的 NMI 进行色谱分离。在通过 13C NMR 光谱表征产品期间，观察到 13C-14N 和 13C-31P 偶联。
• NOVEL LIPID
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP3020701B1

  公开（公告）日：2018-09-26
• [EN] METHOD FOR PRODUCING AN IONIZABLE LIPID<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN LIPIDE IONISABLE
  申请人：[en]NANOVATION THERAPEUTICS INC.

  公开号：WO2022246555A1

  公开（公告）日：2022-12-01

  Provided herein is a method for producing an ionizable lipid that comprises: (i) reacting fatty esters in a Claisen condensation reaction in the presence of a catalyst, the Claisen condensation employing a weak base and carried out at a temperature of between -10 and 60 degrees Celsius to produce a ketoester; (ii) reacting the ketoester produced in step (i) under conditions to produce a ketone from the ketoester in one or more steps via a hydrolysis and decarboxylation of the ketoester; and (iii) preparing the ionizable lipid from the ketone thereof using one or more synthesis steps resulting in an addition of an ionizable head group moiety to (a) the ketone; or (b) an alcohol produced from an optional reduction of the ketone to produce the alcohol, thereby producing the ionizable lipid. The ionizable lipid produced in step (iii) may be formulated in a drug delivery vehicle.