(2E,4E)-octadienoic acid | 22329-75-5

• 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: (2E,4E)-octadienoic acid
• 英文别名: (2E,4E)-octa-2,4-dienoic acid；(E,E)-2,4-Octadienoic acid；Octadienoic acid
• CAS: 22329-75-5
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: QZGIOJSVUOCUMC-YTXTXJHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (2E,4E)-octadienoic acid 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 反,反-2,4-辛二烯醇
  参考文献：
  名称：

  Pellitorine Isomers. III. The Synthesis of N-Isobutyl-trans-4-trans-6-decadienamide and the Structure of Spilanthol¹

  摘要：

  DOI：

  10.1021/ja01600a071
• 作为产物：
  描述：

  2-已烯醛 在 lithium hydroxide monohydrate 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 65.5h， 生成 (2E,4E)-octadienoic acid
  参考文献：
  名称：

  Total Synthesis and Antibacterial Testing of the A54556 Cyclic Acyldepsipeptides Isolated fromStreptomyces hawaiiensis

  摘要：

  The first total synthesis of all six known A54556 acyldepsipeptide (ADEP) antibiotics from Streptomyces hawaiiensis is reported. This family of compounds has a unique mechanism of antibacterial action, acting as activators of caseinolytic protease (ClpP). Assembly of the 16-membered depsipeptide core was accomplished via a pentafluorophenyl ester-based macrolactamization strategy. Late stage amine deprotection was carried out under neutral conditions by employing a mild hydrogenolysis strategy, which avoids the formation of undesired ring-opened depsipeptide side products encountered during deprotection of acid-labile protecting groups. The free amines were found to be significantly more reactive toward late stage amide bond formation as compared to the corresponding ammonium salts, giving final products in excellent yields. A thorough NMR spectroscopic analysis of these compounds was carried out to formally assign the structures and to aid with the spectroscopic assignment of ADEP analogues. The identity of two of the structures was confirmed by comparison with biologically produced samples from S. hawaiiensis. An X-ray crystallographic analysis of an ADEP analogue reveals a conformation similar to that found in cocrystal structures of ADEPs with ClpP protease. The degree of antibacterial activity of the different compounds was evaluated in vitro using MIC assays employing both Gram-positive and Gram-negative strains and a fluorescence-based biochemical assay.

  DOI：

  10.1021/np500158q

文献信息

• Synthesis and Preliminary Biological Characterization of New Semisynthetic Derivatives of Ramoplanin
  作者：Romeo Ciabatti、Sonia I. Maffioli、Gianbattista Panzone、Augusto Canavesi、Elena Michelucci、Paolo S. Tiseni、Ettore Marzorati、Anna Checchia、Matteo Giannone、Daniela Jabes、Gabriella Romanò、Cristina Brunati、Gianpaolo Candiani、Franca Castiglione

  DOI：10.1021/jm070042z

  日期：2007.6.1

  of the new ramoplanin derivatives showed antimicrobial activity similar to that of the natural precursor coupled with a significantly improved local tolerability. Among them the derivative in which the 2-methylphenylacetic acid has replaced the di-unsaturated fatty acid side chain (48) was selected as the most interesting compound and submitted to further in vitro and in vivo characterization studies

  雷莫拉宁是一种糖脂肽肽抗生素，对革兰氏阳性细菌（包括耐万古霉素的肠球菌）具有活性。雷莫拉宁通过不同于糖肽的机制抑制细菌细胞壁的生物合成，因此对这些抗生素没有交叉耐药性。到目前为止，由于静脉内注射时局部耐受性低，因此一直无法阻止雷莫拉汀的全身使用。为了克服这个问题，选择性去除了拉莫普林的脂肪酸侧链，并用各种不同的羧酸代替。许多新的雷莫拉宁衍生物显示出与天然前体相似的抗微生物活性，并具有明显改善的局部耐受性。
• Synthesis and Biological Evaluation of Hoshionolactam‐Based Compounds
  作者：Gorakhnath R. Jachak、Drishya Elizebath、Anurag Shukla、Dhanasekaran Shanmugam、D. Srinivasa Reddy

  DOI：10.1002/ejoc.202001588

  日期：2021.4.22

  To reveal the structure activity relationship of hoshinolactam, a few new analogues around hoshinolactam scaffold were synthesized using readily available starting materials. The synthesized hoshinolactam (mixture of two diastereomers), and related analogues were tested for their anti‐trypanosamal activity to which the synthesized analogues were less potent than the parent natural product.

  为了揭示鼻甲内酰胺的结构活性关系，使用容易获得的起始原料合成了鼻甲内酰胺支架周围的一些新类似物。测试了合成的鼻内酰胺（两种非对映异构体的混合物）和相关类似物的抗胰锥虫活性，合成后的类似物的效力比其母体天然产物的效力低。
• Iridium-Catalyzed Aerobic α,β-Dehydrogenation of γ,δ-Unsaturated Amides and Acids: Activation of Both α- and β-C–H bonds through an Allyl–Iridium Intermediate
  作者：Zhen Wang、Zhiqi He、Linrui Zhang、Yong Huang

  DOI：10.1021/jacs.7b11351

  日期：2018.1.17

  Direct aerobic α,β-dehydrogenation of γ,δ-unsaturated amides and acids using a simple iridium/copper relay catalysis system is described. We developed a new strategy that overcomes the challenging issue associated with the low α-acidity of amides and acids. Instead of α-C-H metalation, this reaction proceeds by β-C-H activation, which results in enhanced α-acidity. Conjugated dienamides and dienoic acids

  描述了使用简单的铱/铜中继催化系统对 γ,δ-不饱和酰胺和酸进行直接有氧 α,β-脱氢。我们开发了一种新策略来克服与酰胺和酸的低 α 酸度相关的挑战性问题。该反应不是 α-CH 金属化，而是通过 β-CH 活化进行，从而导致 α-酸性增强。共轭二酰胺和二烯酸通过该反应以优异的产率合成，该反应使用简单的反应方案。机理实验表明催化剂静止状态机制，其中 α-CH 和 β-CH 裂解都被加速。
• Highly Diastereo- and Enantioselective Synthesis of Cyclohepta[<i>b</i> ]indoles by Chiral-Phosphoric-Acid-Catalyzed (4+3) Cycloaddition
  作者：Coralie Gelis、Guillaume Levitre、Jérémy Merad、Pascal Retailleau、Luc Neuville、Géraldine Masson

  DOI：10.1002/anie.201807069

  日期：2018.9.10

  A highly enantio‐ and diastereoselective formal (4+3) cycloaddition of 1,3‐diene‐1‐carbamates with 3‐indolylmethanols in the presence of a chiral phosphoric acid catalyst is reported. The approach described herein provides efficient access to 6‐aminotetrahydrocyclohepta[b]indoles in good yields with mostly complete diastereoselectivity and excellent levels of enantioselectivity (>98:2 dr and up to

  据报道，在手性磷酸催化剂存在下，将1,3-二烯-1-氨基甲酸酯与3-二吲哚甲醇进行高度对映体和非对映体选择性的（4 + 3）环加成反应。本文所述方法可高效获得6-氨基四氢环庚七[b]吲哚，且具有几乎完全的非对映选择性和极佳的对映选择性（> 98：2 dr，最高98％ee）。温和的反应条件，简便的放大比例和广泛的衍生化功能突出了该方法的实用性。机理研究表明，在手性催化磷酸根和中间体碳正离子之间形成离子对之后，环加成反应会逐步发生。
• [EN] BRYOSTATIN COMPOUNDS AND METHODS OF PREPARING THE SAME<br/>[FR] COMPOSÉS DE BRYOSTATINE ET PROCÉDÉS DE PRÉPARATION CORRESPONDANTS
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2018067382A1

  公开（公告）日：2018-04-12

  Methods for preparing a variety of bryostatin compounds are provided. The subject methods provide for preparation of bryostatin 1 in multi-gram quantities in a low and unprecedented number of convergent synthetic steps from commercially available materials. The subject methods are scalable with low estimated material costs and can provide enough material to meet clinical needs. Also provided are a variety of bryostatin analog compounds, and prodrug forms thereof, which are synthetically accessible via the subject methods and pharmaceutical compositions including the same.

  提供了制备多种海鞘醇化合物的方法。这些方法可以在低成本和前所未有的少量合成步骤中，从商业可获得的原料中制备出多克量的海鞘醇1。这些方法具有可扩展性，估计材料成本低，并且可以提供足够的材料以满足临床需求。此外，还提供了一系列海鞘醇类似物化合物及其前药形式，通过这些方法可以合成，包括这些化合物的药物组合物。