1-nonadecyne | 26186-01-6

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 1-nonadecyne
• 英文别名: nonadec-1-yne
• CAS: 26186-01-6
• 化学式: C₁₉H₃₆
• 分子量: 264.495
• InChiKey: KOGJOFWBMIOBCC-UHFFFAOYSA-N

物化性质

• 熔点：
  33.01°C
• 沸点：
  327.72°C (estimate)
• 密度：
  0.8054

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  19
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-nonadecyne 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 、 甲胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 正戊烷 、 苯 为溶剂， 反应 5.0h， 生成 4-(triaconta-10,12-diynoylamino)-2,2,6,6-tetramethylpiperidine-1-oxyl
  参考文献：
  名称：

  长链二炔酸的杂环衍生物

  摘要：

  2-氨基吡啶、2-氨基嘧啶、4-氨基-2,2,6,6-四甲基哌啶-1-氧基和4-羟基-2,2,6,6-四甲基哌啶-1-氧基的酰基衍生物获自长链二炔酰氯和相应的杂环化合物。在水表面上展开单层的等温线表明，烃链的延长和这些化合物中的吡啶基被更亲水的嘧啶基取代，使膜更加凝聚。硝酰基自由基的长链酰基衍生物形成具有低塌陷压力的单层。记录了这些自由基在光聚合之前和之后的 Langmuir-Blodgett 膜的 ESR 光谱。

  DOI：

  10.1007/bf00707229
• 作为产物：
  描述：

  硬酯酸甲酯C18 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 苯 为溶剂， 反应 72.5h， 生成 1-nonadecyne
  参考文献：
  名称：

  A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles

  摘要：

  Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave alpha-(benzotriazol-1-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, alpha-(benzotriazol-1-yl) ketones 22 can be accessed by the reaction of alpha-(benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl)hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of hydrazones 5, 21, and 28 with n-butyllithium in diethyl ether resulted in the elimination of the tosyl group, dinitrogen, and benzotriazolyl group to afford the corresponding acetylenes 9, 23, and 29 in good yields. When alpha-(benzotriazol-1-yl) 1-alpha-phenoxy hydrazones 14 were treated with methyllithium, n-butyllithium, or phenyllithium, alkynes 18 were obtained, in which phenoxy groups were replaced by the lithium reagents.

  DOI：

  10.1021/jo962291t

文献信息

• [EN] PHOSPHORUS IMIDAZOQUINOLINE AMINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND THERAPEUTIC METHODS THEREOF<br/>[FR] DÉRIVÉS D'AMINE D'IMIDAZOQUINOLINE DE PHOSPHORE, COMPOSITIONS PHARMACEUTIQUES ET PROCÉDÉS THÉRAPEUTIQUES CORRESPONDANTS
  申请人：YU NINGHUI

  公开号：WO2020163118A1

  公开（公告）日：2020-08-13

  The invention provides novel phosphorus imidazoquinoline amine derivatives, having agonistic activities to Toll-like receptors (TLRs), in particular TLR7 and/or TLR8, pharmaceutical compositions thereof, and methods of treatment, reduction or prevention of certain diseases or conditions mediated by or associated with TLR7 and/or TLRS, e.g., cancer, graft rejection, autoimmunity, inflammation allergy, asthma, infection, sepsis, and immunodeficiency.

  该发明提供了新型磷酸嘌呤喹啉胺衍生物，具有对Toll样受体（TLRs）的激动活性，特别是对TLR7和/或TLR8的激动活性，以及其药物组合物，以及治疗、减少或预防由TLR7和/或TLRs介导或相关的某些疾病或症状的方法，例如癌症、移植排斥、自身免疫、炎症过敏、哮喘、感染、败血症和免疫缺陷。
• Synthesis of a-O- and a-S-Glycosphingolipids Related to Sphingomonous cell Wall Antigens Using Anomerisation
  作者：Wayne Pilgrim、Ciaran O'Reilly、Paul Murphy

  DOI：10.3390/molecules180911198

  日期：——

  Analogues of glycolipids from Spingomonadacaece with O- and S- and SO2-linkages have been prepared using chelation induced anomerisation promoted by TiCl4. Included are examples of the anomerisation of intermediates with O- and S-glycosidic linkages as well as isomerisation of β-thioglycuronic acids (β-glycosyl thiols). The β-O-glucuronide and β-O-galacturonide precursors were efficiently prepared using benzoylated trichloroacetimidates. β-Glycosyl thiols were precursors to β-S-derivatives. Triazole containing mimics of the natural glycolipids were prepared using CuI promoted azide-alkyne cycloaddition reactions in THF. The glycolipid antigens are being evaluated currently for their effects on iNKT cells.

  来自Spingomonadacaece的糖脂类类似物，具有O-、S-和SO2-连接，通过TiCl4催化的螯合诱导的异构化进行了制备。其中包括具有O-和S-糖苷键的中间体异构化的例子，以及β-硫葡萄糖醇酸（β-糖苷硫醇）的异构化。β-O-葡萄糖醛酸酯和β-O-半乳糖醛酸酯的前体采用苯甲酰化三氯乙酰胺高效制备。β-糖苷硫醇是β-S-衍生物的前体。含有三唑的天然糖脂类模仿物使用CuI催化的叠氮烷炔环加成反应在THF中制备。当前正在评估这些糖脂抗原对iNKT细胞的影响。
• Synthesis and Evaluation of Sphingolipid Analogues
  作者：Thresen Mathew、Andreas Billich、Marco Cavallari、Frederic Bornancin、Peter Nussbaumer、Gennaro De Libero、Andrea Vasella

  DOI：10.1002/cbdv.200900013

  日期：2009.5

  The analogues 7-9 of 7-oxaceramide and 7-oxasphingosine were synthesized from the known azidosphingosine 21. The 1,4-disubstituted 1,2,3-triazole analogues 10-16 of ceramides were synthesized by the click reaction of the known azide 24. None of the analogues 7-15 was active as inhibitor of SPHK type 1 and of acid sphingomyelinase, whereas 16 is a weak inhibitor of SPHK1. Triazoles 10, 11, and 15 did

  由已知的叠氮鞘氨醇21合成7-氧杂草酰胺和7-氧杂萘新的类似物7-9。通过已知的叠氮化物的点击反应合成了1，4-二取代的1,2,3-三唑的神经酰胺类似物10-16。 24.类似物7-15均没有活性作为SPHK 1型和酸性鞘磷脂酶的抑制剂，而16种是SPHK1的弱抑制剂。三唑10、11和15不会抑制CerK引起的神经酰胺磷酸化，当被人类CD1d转染的抗原呈递细胞（APC）呈递时，7、8和10-15均不会激活不变的自然杀伤T（iNKT）细胞克隆。或通过板结合的人CD1d [55]。三唑14和15阻止α-半乳糖基神经酰胺（α-GalCer）与板结合的人CD1d结合，并防止随后的T细胞对α-GalCer的反应。
• WO2020160054A5
  申请人：——

  公开号：WO2020160054A5

  公开（公告）日：2023-01-05
• Efficient asymmetric synthesis of long chain methyl-branched hydrocarbons, components of the contact sex pheromone of females of the cerambycid beetle, Neoclytus acuminatus acuminatus
  作者：Jan E. Bello、Jocelyn G. Millar

  DOI：10.1016/j.tetasy.2013.05.021

  日期：2013.7

  Both enantiomers of 7-methylheptacosane and 7-methylpentacosane, the major components of the female-produced contact sex pheromone of the red-headed ash borer beetle (Neoclytus acuminatus accuminatus) were synthesized in 62-68% overall yield (six steps) via alkynylation of the triflate of a shared chiral alcohol intermediate (R)- or (S)-2-methyloctanol. The enantiomers of the shared intermediate were prepared via acylation and subsequent asymmetic methylation of (R)- and (S)-4-isopropyloxazolidin-2-one chiral auxiliaries, respectively. The methodology can be readily adapted for the preparation of analogues with any desired chain length and methyl branch positions. (C) 2013 Elsevier Ltd. All rights reserved.