2-nonadecyn-1-ol | 72443-48-2

• 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: 2-nonadecyn-1-ol
• 英文别名: nonadec-2-yn-1-ol
• CAS: 72443-48-2
• 化学式: C₁₉H₃₆O
• 分子量: 280.494
• InChiKey: CAURIUJAQYBXHU-UHFFFAOYSA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  257.1±8.0 °C(Predicted)
• 密度：
  0.868±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-nonadecyn-1-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium on activated charcoal 亚磷酸三苯酯 、 copper(l) iodide 、 potassium tert-butylate 、 氢气 、 碘 、 lithium 、 1,2-丙二胺 、 二异丙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， -78.0~25.0 ℃ 、500.0 kPa 条件下， 反应 52.67h， 生成 grandinolide
  参考文献：
  名称：

  Total Syntheses of (−)-Grandinolide and (−)-Sapranthin by the Sharpless Asymmetric Dihydroxylation of Methyltrans-3-Pentenoate: Elucidation of the Stereostructure of (−)-Sapranthin

  摘要：

  Methyl trans-3-pentenoate (7) was converted into the cis-substituted gamma-lactone 8 in a single step with 78 % ee. The derived enolate dilithio-8 was alkylated trans-selectively with primary iodoalkanes. with 1-iodobutane dilithio-8 afforded, after esterification with isovaleroyl chloride, the epi-blast mycinone 9, Dilithio-8 gave (-)-grandinolide (11) with 1-iodo-19-phenylnonadecane (20), A third trans-selective alkylation of dilithio-8 was undertaken with 16-iodo-1.5-hexadecadiene-7,9-diyne (21). This gave the gamma-lactone 12. which had the published relative configuration of (-)-sapranthin but different spectroscopic data, When the OH group of lactone 8 was inverted (to hydroxylactone 40) and the derived enolate dilithio-40 alkylated with iodide 21, lactone 41 resulted, Its H-1 and C-13 NMR spectra and the sign and value of optical rotation coincide with the data of natural sapranthin, These findings establish that (-)-sapranthin possesses the relative and absolute configuration of stereoformula 41. The synthesis of iodide 21 was performed via the dienoic carboxylic ester trans-23 which stemmed from the Claisen-Ireland rearrangement (27 --> 28/29)/esterification (28/29 --> 26)/Cope rearrangement (26 - 23) sequence shown in Scheme 5.

  DOI：

  10.1002/(sici)1521-3765(19981102)4:11<2342::aid-chem2342>3.0.co;2-q
• 作为产物：
  描述：

  2-nonadec-2-ynoxytetrahydropyran 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 以75%的产率得到2-nonadecyn-1-ol
  参考文献：
  名称：

  具有增强药代动力学特性的 HIV NtRTI 替诺福韦的 ω 功能化脂质前药

  摘要：

  替诺福韦 (TFV) 是许多针对 HIV/AIDS 患者的联合抗逆转录病毒疗法中的基石核苷酸逆转录酶抑制剂 (NtRTI)。由于细胞渗透性和口服生物利用度较差，TFV 作为 FDA 批准的两种前药之一施用，这两种前药都会在肝脏和/或血浆中过早代谢。这种过早的前药加工会消耗每次口服剂量的很大一部分，并在长期给药时引起肾脏、骨骼和肝脏毒性。尽管 TFV exalidex (TXL)（一种 TFV 的磷脂衍生前药）旨在解决这个问题，但临床药代动力学研究表明大量的肝提取，将 TXL 的临床开发转向 HBV。为了规避这种代谢缺陷，我们合成并评估了 ω 功能化的 TXL 类似物，其肝稳定性显着提高。这项工作导致了化合物21和23的鉴定，它们在人肝微粒体中表现出比 TXL 更长的t 1/2值、有效的体外抗 HIV 活性以及增强的体内药代动力学特性。

  DOI：

  10.1021/acs.jmedchem.1c01083

文献信息

• [EN] NUCLEOSIDE PRODRUGS AND USES RELATED THERETO<br/>[FR] PROMÉDICAMENTS NUCLÉOSIDIQUES ET LEURS UTILISATIONS
  申请人：UNIV EMORY

  公开号：WO2021035214A1

  公开（公告）日：2021-02-25

  Disclosed are acyclic nucleoside prodrugs with improved metabolic stability and oral bioavailability. In general, the prodrugs are derivatives of acyclic nucleoside phosphonates containing a lipid-like moiety that can increase oral absorption and subsequent stability in the liver and plasma. Preferably, the lipid-like moiety can resist enzyme-mediated ω-oxidation, such as ω -oxidation catalyzed by cytochrome P450 enzymes. Also disclosed are pharmaceutical formulations of the acyclic nucleoside prodrugs. The acyclic nucleoside prodrugs and pharmaceutical formulations thereof can be used to treat viral infections, such as HIV infections, and/or viral-associated cancer, such as HPV-associated cancers.

  揭示了具有改善代谢稳定性和口服生物利用度的非环核苷前药。一般来说，这些前药是非环核苷膦酸酯的衍生物，含有类似脂质的基团，可以增加口服吸收并在肝脏和血浆中提高稳定性。最好，类似脂质的基团可以抵抗酶介导的ω-氧化，例如细胞色素P450酶催化的ω-氧化。还揭示了非环核苷前药的药物配方。这些非环核苷前药及其药物配方可用于治疗病毒感染，如HIV感染，和/或病毒相关癌症，如HPV相关癌症。
• Phosphocholine derivative inhibitors of phospholipase A.sub.2
  申请人：American Cyanamid Company

  公开号：US05144045A1

  公开（公告）日：1992-09-01

  Phospocholine derivatives having the formula: ##STR1## in which W, Z, Q and R are described in the specification are disclosed as useful for inhibiting the enzyme phospholipase A.sub.2. Methods of making and using the compounds are also disclosed.

  公开了具有以下公式的磷酸胆碱衍生物：##STR1## 其中在说明书中描述的W、Z、Q和R被公开为用于抑制磷脂酶A.sub.2酶的有用物质。还公开了制备和使用这些化合物的方法。
• Glycerol derivatives, their preparation and their therapeutic use
  申请人：Sankyo Company Limited

  公开号：EP0238202A2

  公开（公告）日：1987-09-23

  Glycerol derivatives having at least one heterocyclic group on the 3 or 2 position and a group of formula -Y-D-Q on the 1 position (in which Y represents oxygen, sulphur, -NR3-, -X-CO-R'-, -R4-CO-X-, -NR'-CO-, -CO-NR3-or -X-P-(O) (OH)-O-, where -NR3-is optionally protected imino, R4 represents a direct bond or -NR3; and X represents oxygen or sulphur; D represents optionally substituted C1-C14 alkylene; and Q represents a nitrogen-containing heterocyclic group or an amino group either of which is optionally quatemized) are PAF antagonists which may be used to treat asthma, inflammation and shock. They may be prepared by reacting a glycerol derivative having an active group at the 1-position with an appropriate compound to introduce the desired group.

  甘油衍生物在 3 或 2 位上至少有一个杂环基团，在 1 位上有一个式-Y-D-Q 的基团（其中 Y 代表氧、硫、-NR3-、-X-CO-R'-、-R4-CO-X-、-NR'-CO-、-CO-NR3-或 -X-P-(O)(OH)-O-，其中 -NR3- 是可选的受保护亚氨基，R4 代表直接键或 -NR3；X 代表氧或硫；D 代表任选取代的 C1-C14 亚烷基；Q 代表含氮杂环基团或氨基，二者任选其一被藜麦化）是 PAF 拮抗剂，可用于治疗哮喘、炎症和休克。制备方法是将 1 位具有活性基团的甘油衍生物与适当的化合物反应，引入所需的基团。
• Isomerization of internal triple bonds of alkyn-1-ols with sodium hydride in 1,3-diaminopropane
  作者：Suzanne R. Macaulay

  DOI：10.1021/jo01292a042

  日期：1980.2
• Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I
  作者：Yasunao Hattori、Hiroyuki Konno、Masato Abe、Hideto Miyoshi、Tetsuhisa Goto、Hidefumi Makabe

  DOI：10.1016/j.bmc.2007.02.002

  日期：2007.4

  The first synthesis of two possible diastereomers of tonkinelin was achieved. By comparison of the optical rotation of two candidates of tonkinelin and the natural compound, it is suggested that the absolute configuration of natural tonkinelin is likely to be (17S,18S). The inhibitory activity of these compounds was examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin. (c) 2007 Elsevier Ltd. All rights reserved.