N-lauroyltetradecanylamine | 858482-12-9

• 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: N-lauroyltetradecanylamine
• 英文别名: Dodecanamide, N-tetradecyl-；N-tetradecyldodecanamide
• CAS: 858482-12-9
• 化学式: C₂₆H₅₃NO
• 分子量: 395.713
• InChiKey: SGCAXQFEDYHNPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  28
• 可旋转键数：
  23
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-lauroyltetradecanylamine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以1.4 g的产率得到N-dodecanyltetradecanylamine
  参考文献：
  名称：

  [EN] NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
  [FR] NOUVEAUX LIPIDES ET FORMULATIONS NANOPARTICULAIRES LIPIDIQUES POUR L'ADMINISTRATION D'ACIDES NUCLÉIQUES

  摘要：

  提供具有以下结构的化合物：(I)或其药用盐、互变异构体或立体异构体，其中R1a、R1b、R2a、R2b、R3a、R3b、R4a、R4b、R5、R6、R7、R8、R9、L1、L2、a、b、c、d和e的定义如本文所述。还提供了将这些化合物用作脂质纳米粒子制剂的组分、包含这些化合物的组合物以及其使用和制备方法。

  公开号：

  WO2015199952A1
• 作为产物：
  描述：

  正十四烷基铵 在 N-羟基丁二酰亚胺 、 lithium aluminium tetrahydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 N-lauroyltetradecanylamine
  参考文献：
  名称：

  [EN] NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
  [FR] NOUVEAUX LIPIDES ET FORMULATIONS NANOPARTICULAIRES LIPIDIQUES POUR L'ADMINISTRATION D'ACIDES NUCLÉIQUES

  摘要：

  提供具有以下结构的化合物：(I)或其药用盐、互变异构体或立体异构体，其中R1a、R1b、R2a、R2b、R3a、R3b、R4a、R4b、R5、R6、R7、R8、R9、L1、L2、a、b、c、d和e的定义如本文所述。还提供了将这些化合物用作脂质纳米粒子制剂的组分、包含这些化合物的组合物以及其使用和制备方法。

  公开号：

  WO2015199952A1

文献信息

• Reaction of Amphipathic-Type Thioester and Amine with Hydrophobic Effect in Water
  作者：Chiaki Kuroda、Atsushi Torihata

  DOI：10.1055/s-0030-1261165

  日期：2011.9

  The title reaction was studied using sodium 3-(1-oxo­dodec-1-yl)thio- and 3-(1-oxohept-1-yl)thiopropanoate with various chain lengths of amines. The yields of the amides were found to depend on both the chain length of the thioester and that of amine, suggesting the presence of hydrophobic interaction. The amides were obtained in better yields after addition of sodium fluoride. Acylation (dodecanoylation) of some hydrophobic amino acids was also studied to obtain the corresponding amides.

  标题反应采用了不同链长度的胺与三-(1-氧代十二烷-1-基)硫和三-(1-氧代庚烷-1-基)硫丙酸钠进行研究。发现酰胺的产率不仅依赖于硫酯的链长度，还依赖于胺的链长度，这表明存在疏水相互作用。在添加氟化钠后，酰胺的产率有所提高。还研究了一些疏水性氨基酸的酰化（十二酰化），以获得相应的酰胺。
• Hydrophobic Effect and Substrate Specificity in Reaction of Thioester and Amine in Water
  作者：Atsushi Torihata、Chiaki Kuroda

  DOI：10.1246/bcsj.20100143

  日期：2010.12.15

  extent of hydrophobic effect in amidation reaction of alkyl thioester with alkylamine in water was studied. The yield of the products was primarily dependent on the alkyl group of amine. For example, the reaction of S-dodecyl dodecanethioate with dodecylamine proceeded in good yield, while the reaction did not occur with cyclohexylamine, piperidine, and dipropylamine. The effect of chain length of n-alkylamine

  研究了烷基硫酯与烷基胺在水中的酰胺化反应中疏水作用的程度。产物的产率主要取决于胺的烷基。例如，S-十二烷基硫代酸酯与十二烷基胺的反应收率良好，而与环己胺、哌啶和二丙胺的反应则没有发生。研究了正烷基胺链长的影响以表明存在疏水作用。酰胺的产率也次要取决于硫酯的烷基，但影响比胺小。
• NOVEL LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
  申请人：Acuitas Therapeutics Inc.

  公开号：US20150376115A1

  公开（公告）日：2015-12-31

  Compounds are provided having the following structure: or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R 1a , R 1b , R 2a , R 2b , R 3a , R 3b , R 4a , R 4b , R 5 , R 6 , R 7 , R 8 , R 9 , L 1 , L 2 , a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.

  提供具有以下结构的化合物：其中R1a，R1b，R2a，R2b，R3a，R3b，R4a，R4b，R5，R6，R7，R8，R9，L1，L2，a，b，c，d和e的药物可接受的盐，互变异构体或立体异构体，如此处所定义。还提供将该化合物用作脂质纳米粒子配方的组分，用于传递治疗剂的组成物以及其使用和制备方法。
• Lipids and lipid nanoparticle formulations for delivery of nucleic acids
  申请人：ACUITAS THERAPEUTICS INC.

  公开号：US10106490B2

  公开（公告）日：2018-10-23

  Compounds are provided having the following structure: or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R1a, R1b, R2a, R2b, R3a, R3b, R4a, R4b, R5, R6, R7, R8, R9, L1, L2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.

  提供具有以下结构的化合物： 或其药学上可接受的盐、同系物或立体异构体，其中 R1a、R1b、R2a、R2b、R3a、R3b、R4a、R4b、R5、R6、R7、R8、R9、L1、L2、a、b、c、d 和 e 如本文所定义。本发明还提供了作为脂质纳米粒子制剂组分的化合物在递送治疗剂中的用途、包含本发明化合物的组合物及其使用和制备方法。
• LIPIDS AND LIPID NANOPARTICLE FORMULATIONS FOR DELIVERY OF NUCLEIC ACIDS
  申请人：Acuitas Therapeutics, Inc.

  公开号：US20210107861A1

  公开（公告）日：2021-04-15

  Compounds are provided having the following structure: or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R 1a , R 1b , R 2a , R 2b , R 3a , R 3b , R 4a , R 4b , R 5 , R 6 , R 7 , R 8 , R 9 , L 1 , L 2 , a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.