octadec-9(Z)-enoyl azide | 77165-66-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: octadec-9(Z)-enoyl azide
• 英文别名: Oleic azid；(Z)-octadec-9-enoyl azide
• CAS: 77165-66-3
• 化学式: C₁₈H₃₃N₃O
• 分子量: 307.48
• InChiKey: UDXZIRFMBYTZPD-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  octadec-9(Z)-enoyl azide 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 45.0h， 生成 (8Z)-heptadec-8-en-1-amine
  参考文献：
  名称：

  Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials

  摘要：

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.

  DOI：

  10.1021/jo301659c
• 作为产物：
  描述：

  在 sodium azide 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 octadec-9(Z)-enoyl azide
  参考文献：
  名称：

  Direct and facile synthesis of acyl azides from carboxylic acids using the trichloroisocyanuric acid–triphenylphosphine system

  摘要：

  一种温和、高效、实用的方法，可通过使用安全且廉价的混合试剂三氯异氰尿酸-三苯基膦，从羧酸一步合成酰胺基化合物。

  DOI：

  10.1139/cjc-2011-0493

文献信息

• Direct, facile synthesis of acyl azides and nitriles from carboxylic acids using bis(2-methoxyethyl)aminosulfur trifluoride
  作者：Cyrous O. Kangani、Billy W. Day、David E. Kelley

  DOI：10.1016/j.tetlet.2007.06.119

  日期：2007.8

  A mild, efficient, and practical method for the one-step synthesis of acyl azides from carboxylic acids using bis(2-methoxyethyl)aminosulfur trifluoride is described. The reaction was easily extended to the synthesis of the corresponding nitriles by the inclusion of phosphorous reagents. The method can be applied to the synthesis of optically active nitriles in high yields, and is compatible with fluorous

  描述了一种温和，有效和实用的方法，用于使用双（2-甲氧基乙基）氨基三氟化硫从羧酸一步合成酰基叠氮化物。通过包含磷试剂，该反应易于扩展至相应腈的合成。该方法可用于高产率地合成旋光腈，并且与氟代膦酸酯相容。
• CHEMICAL MODIFICATIONS OF MONOMERS AND OLIGONUCLEOTIDES WITH CYCLOADDITION
  申请人：Manoharan Muthiah

  公开号：US20120035115A1

  公开（公告）日：2012-02-09

  The invention features compounds of formula I or II: In one embodiment, the invention relates compounds and processes for conjugating ligand to oligonucleotide. The invention further relates to methods for treating various disorders and diseases such as viral infections, bacterial infections, parasitic infections, cancers, allergies, autoimmune diseases, immunodeficiencies and immunosuppression.

  该发明涉及公式I或II的化合物：在一种实施方式中，该发明涉及化合物和用于将配体与寡核苷酸结合的过程。该发明进一步涉及治疗各种疾病和疾病的方法，例如病毒感染、细菌感染、寄生虫感染、癌症、过敏、自身免疫疾病、免疫缺陷和免疫抑制。
• Reduction of Azides with Zinc Borohydride
  作者：Brindaban C. Ranu、Arunkanti Sarkar、Rupak Chakraborty

  DOI：10.1021/jo00094a021

  日期：1994.7

  Zinc borohydride in 1,2-dimethoxyethane provides an efficient procedure for the reduction of organic azides. Aroyl, acyl, and arylsulfonyl azides readily undergo reduction at room temperature to produce amides and sulfonamides in excellent yields; however, substitution with electron-withdrawing groups in the aroyl azides leads to the corresponding benzyl alcohols. Reduction of aryl and alkyl azides has also been achieved in high yields, under some modified conditions.
• Design and Synthesis of Lipids for the Fabrication of Functional Lipidic Cubic-Phase Biomaterials
  作者：Yazmin M. Osornio、Peter Uebelhart、Silvan Bosshard、Fabian Konrad、Jay S. Siegel、Ehud M. Landau

  DOI：10.1021/jo301659c

  日期：2012.12.7

  A series of novel lipids with designed functionalities were synthesized. These lipids are based on conjugation of alpha-amino acids and their esters, cationic, anionic, neutral, and photochromic moieties to the lipophilic 9-cis octadecenyl chains by amide, ester, thioester, or amine bonds. Because of the plasticity of lipidic cubic phases, it is envisaged that when mixed with monooleoyl-rac-glycerol (monoolein, MO) and water at appropriate proportions, they would assemble to form bicontinuous lipidic cubic phases (LCPs) that exhibit the well-known material properties of LCPs such as phase stability, optical transparency, and chemical permeability. Moreover, due to the nature and position of the functionality at the headgroup region, we envision them to perform as functional materials by design.
• Direct and facile synthesis of acyl azides from carboxylic acids using the trichloroisocyanuric acid–triphenylphosphine system
  作者：Batool Akhlaghinia、Hamed Rouhi-Saadabad

  DOI：10.1139/cjc-2011-0493

  日期：2013.3

  A mild, efficient, and practical method for the one-step synthesis of acyl azides from carboxylic acids using a safe and inexpensive mixed reagent, trichloroisocyanuric acid–triphenylphosphine, is described.

  一种温和、高效、实用的方法，可通过使用安全且廉价的混合试剂三氯异氰尿酸-三苯基膦，从羧酸一步合成酰胺基化合物。