2-icosanoic acid | 34452-14-7

• 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-icosanoic acid
• 英文别名: 2-ICA；2-Eicosynoic acid；icos-2-ynoic acid
• CAS: 34452-14-7
• 化学式: C₂₀H₃₆O₂
• 分子量: 308.505
• InChiKey: QFCRVSLTJJEZLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  79.08°C (estimate)
• 沸点：
  455.31°C (rough estimate)
• 密度：
  0.9379 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-icosanoic acid 在 bis(bis(trimethylsilyl)amido)tin(II) 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 15.5h， 生成 trichonine
  参考文献：
  名称：

  Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology

  摘要：

  Sakai芳基醛-环酮Aldol-Grob断裂序列被扩展到肉桂醛和环己酮，并将产物改造为吡啶碱类似物。研究了涉及肉桂醛的反应中取代基的影响。当环辛酮或环丁酮替代环己酮或环戊酮时，苯甲醛无法进行Aldol-断裂序列，对此失败的原因进行了研究。对吡哆醛-环丁酮Aldol-断裂产物进行了四碳Wittig同系化，这是通往碱类如retrofractamide A的假设路线，但该方法并不可行。相反，利用Lu和Trost最近披露的炔化学，对易得的吡哆醛-环戊酮产物进行了三碳同系化，以极高的总产率制备了这些碱类。炔异构化还被用于高效合成辣椒碱和几种其他非芳香2E,4E-二烯酸Piper酰胺类碱类。关键词：Piper、酰胺、碱类、杀虫剂、Aldol、断裂、肉桂醛、炔、氧化还原、异构化。

  DOI：

  10.1139/v96-046
• 作为产物：
  描述：

  1-溴十七烷 、 丙炔酸 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 生成 2-icosanoic acid
  参考文献：
  名称：

  Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology

  摘要：

  Sakai芳基醛-环酮Aldol-Grob断裂序列被扩展到肉桂醛和环己酮，并将产物改造为吡啶碱类似物。研究了涉及肉桂醛的反应中取代基的影响。当环辛酮或环丁酮替代环己酮或环戊酮时，苯甲醛无法进行Aldol-断裂序列，对此失败的原因进行了研究。对吡哆醛-环丁酮Aldol-断裂产物进行了四碳Wittig同系化，这是通往碱类如retrofractamide A的假设路线，但该方法并不可行。相反，利用Lu和Trost最近披露的炔化学，对易得的吡哆醛-环戊酮产物进行了三碳同系化，以极高的总产率制备了这些碱类。炔异构化还被用于高效合成辣椒碱和几种其他非芳香2E,4E-二烯酸Piper酰胺类碱类。关键词：Piper、酰胺、碱类、杀虫剂、Aldol、断裂、肉桂醛、炔、氧化还原、异构化。

  DOI：

  10.1139/v96-046

文献信息

• Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria
  作者：David J. Sanabria-Ríos、Yaritza Rivera-Torres、Gamalier Maldonado-Domínguez、Idializ Domínguez、Camille Ríos、Damarith Díaz、José W. Rodríguez、Joanne S. Altieri-Rivera、Eddy Ríos-Olivares、Gabriel Cintrón、Nashbly Montano、Néstor M. Carballeira

  DOI：10.1016/j.chemphyslip.2013.12.006

  日期：2014.2

  The first study aimed at determining the structural characteristics needed to prepare antibacterial 2-alkynoic fatty acids (2-AFAs) was accomplished by synthesizing several 2-AFAs and other analogs in 18-76% overall yields. Among all the compounds tested, the 2-hexadecynoic acid (2-HDA) displayed the best overall antibacterial activity against Gram-positive Staphylococcus aureus (MIC = 15.6 mu g/mL), Staphylococcus saprophyticus (MIC = 15.5 mu g/mL), and Bacillus cereus (MIC = 31.3 mu g/mL), as well as against the Gram-negative Klebsiella pneumoniae (7.8 mu g/mL) and Pseudomonas aeruginosa (MIC = 125 mu g/mL). In addition, 2-HDA displayed significant antibacterial activity against methicillin-resistant S. aureus (MRSA) ATCC 43300 (MIC = 15.6 mu g/mL) and clinical isolates of MRSA (MIC = 3.9 mu g/mL). No direct relationship was found between the antibacterial activity of 2-AFAs and their critical micelle concentration (CMC) suggesting that the antibacterial properties of these fatty acids are not mediated by micelle formation. It was demonstrated that the presence of a triple bond at C-2 and the carboxylic acid moiety in 2-AFAs are important for their antibacterial activity. 2-HDA has the potential to be further evaluated for use in antibacterial formulations. (C) 2013 Elsevier Ireland Ltd. All rights reserved.
• LONG CHAIN FATTY ACID FORMULATIONS AND THEIR USE IN INHIBITING SALMONELLA INFECTION
  申请人：CORNELL UNIVERSITY

  公开号：US20200330420A1

  公开（公告）日：2020-10-22

  A method for inhibiting or preventing Salmonella invasion of the intestinal epithelium in a subject, the method comprising enterally administering to the subject a pharmaceutically effective amount of a fatty acid dissolved or suspended in a pharmaceutically acceptable carrier, wherein the fatty acid contains 10 to 30 carbon atoms, wherein the fatty acid is more particularly an unsaturated fatty acid containing 1-4 carbon-carbon double bonds and/or 1 or 2 carbon-carbon triple bonds, or the fatty acid is more particularly a cis-unsaturated fatty acid, or the fatty acid is more particularly a cis-2-unsaturated fatty acid having the formula: wherein n is an integer of 6-26, and the fatty acid optionally includes a second carbon-carbon double bond resulting from removal of two hydrogen atoms on adjacent carbon atoms.
• GOLF BALL
  申请人：Sumitomo Rubber Industries, Ltd.

  公开号：US20210086036A1

  公开（公告）日：2021-03-25

  An object of the present invention is to provide a golf ball having a decreased spin rate on driver shots. The present invention provides a golf ball comprising a spherical core and at least one cover layer covering the spherical core, wherein the spherical core is formed from a rubber composition containing (a) a base rubber, (b) a compound represented by the formula (1) as a co-crosslinking agent, and (c) a crosslinking initiator, (R 1 COO)M(OCOR 2 ) m (1) in the formula (1), M represents a metal atom, m represents 1 or 2, R 1 and R 2 are different from each other, represent an alkenyl group having 2 to 30 carbon atoms or an alkynyl group having 2 to 30 carbon atoms and have a carbon-carbon double bond or a carbon-carbon triple bond at an α-position carbon atom bonding to the carbonyl group, and when m is 2, two of R 2 may be identical to or different from each other.
• US5837732A
  申请人：——

  公开号：US5837732A

  公开（公告）日：1998-11-17
• [EN] ANTIMYCOBACTERIAL COMPOUNDS AND METHOD OF USING SAME<br/>[FR] COMPOSES ANTIMYCOBACTERIENS ET PROCEDES D'UTILISATION
  申请人：ALBERT EINSTEIN COLLEGE OF MEDICINE OF YESHIVA UNIVERSITY, a division of YESHIVA UNIVERSITY

  公开号：WO1996024347A1

  公开（公告）日：1996-08-15

  (EN) The present invention provides a compound having structure (I), wherein R is a branched or unbranched C1-C30 alkyl, alkenyl or alkynyl; or a branched or unbranched C1-C30 alkyl, alkenyl or alkynyl substituted with S, O, N, P, SO2, F, Cl, Br, or I, wherein S, O, N, P, or SO2 replaces at least one -CH2-, and F, Cl, Br, or I replaces at least one H. The present invention also provides a pharmaceutical composition comprising the compound above, as well as a method for treating a mycobacterial disease or infection in a subject in need of such treatment by administering to the subject an effective amount of the compound above.(FR) L'invention concerne un composé possédant la structure suivante: dans laquelle R représente un alkyle, alkényle ou alkynyle C1-C30 ramifié ou non ramifié, ou un alkyle, alkényle ou alkynyle C1-C30 ramifié ou non ramifié substitué par S, O, N, P, SO2, F, Cl, Br ou I, où S, O, N, P ou SO2 remplace au moins un -CH2- et F, Cl, Br ou I remplace au moins un H. L'invention concerne également une composition pharmaceutique comprenant ledit composé, ainsi qu'un procédé de traitement d'une maladie ou d'une infection mycobactérienne chez un sujet par administration audit sujet d'une quantité efficace dudit composé.