6-azidohexanoyl chloride | 5515-02-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 6-azidohexanoyl chloride
• 英文别名: 6-Azidohexanoic chloride
• CAS: 5515-02-6
• 化学式: C₆H₁₀ClN₃O
• 分子量: 175.618
• InChiKey: XJNLPJYSEYKBBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  6
• 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：
  3

反应信息

• 作为反应物：
  描述：

  6-azidohexanoyl chloride 在 吡啶 、 三苯基膦 、 三氟乙酸 作用下， 以 2,4,6-三甲基吡啶 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 42.0h， 生成 6-isothiocyanato-N-[bis[3-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)thioureidomethyl]methyl]hexanamide
  参考文献：
  名称：

  Synthesis and comparative lectin-binding affinity of mannosyl-coated β-cyclodextrin-dendrimer constructs

  摘要：

  通过迭代硫脲形成收敛策略，δ-环糊精与甘露聚糖包裹的树枝状枝条进行单共轭，从而构建了靶向给药系统；多价加合物显示出较高的癌凝集素 A 结合能力和完整的包涵能力。

  DOI：

  10.1039/b003765f
• 作为产物：
  描述：

  6-溴己酸甲酯 在 甲醇 、 sodium azide 、 草酰氯 、 N,N-二甲基甲酰胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-azidohexanoyl chloride
  参考文献：
  名称：

  Inhibition of Lymphoid Tyrosine Phosphatase by Benzofuran Salicylic Acids

  摘要：

  The lymphoid tyrosine phosphatase (Lyp, PTPN22) is a critical negative regulator of T cell antigen receptor (TCR) signaling. A single-nucleotide polymorphism (SNP) in the ptpn22 gene correlates with the incidence of various autoimmune diseases, including type I diabetes, rheumatoid arthritis, and systemic lupus erythematosus. Since the disease-associated allele is a more potent inhibitor of TCR signaling, specific Lyp inhibitors May become valuable in treating autoimmunity. Using a structure-based approach, we synthesized a library of 34 compounds that inhibited Lyp with IC50 values between 0.27 and 6.2 mu M. A reporter assay was employed to screen for compounds that enhanced TCR signaling in cells, and several inhibitors displayed a dose-dependent, activating effect. Subsequent probing for Lyp's direct physiological targets by immunoblot analysis confirmed the ability of the compounds to inhibit Lyp in T cells. Selectivity profiling against closely related tyrosine phosphatases and in silico docking studies with the crystal structure of Lyp yielded valuable information for the design of Lyp-specific compounds.

  DOI：

  10.1021/jm101004d

文献信息

• Formation of 1-Hydroxymethylene-1,1-bisphosphinates through the Addition of a Silylated Phosphonite on Various Trivalent Derivatives
  作者：Jade Dussart-Gautheret、Julia Deschamp、Maelle Monteil、Olivier Gager、Thibaut Legigan、Evelyne Migianu-Griffoni、Marc Lecouvey

  DOI：10.1021/acs.joc.0c01182

  日期：2020.11.20

  handled one-pot synthetic procedure was previously developed for the synthesis of bisphosphinates starting from acyl chlorides. Herein, other trivalent derivatives as acid anhydrides and activated esters were tested to form various bisphosphinates. This modulation of the reactivity can be controlled according to the nature of the acid derivative for the use of sensitive and functionalized substrates

  先前已经开发了一种易于处理的一锅合成方法，用于从酰氯开始合成双膦酸酯。本文中，测试了作为酸酐和活化酯的其他三价衍生物以形成各种双次膦酸酯。可以根据酸衍生物的性质来控制反应性的这种调节，以用于敏感的和功能化的底物。
• Antibacterial agents, and 4-thio azetidinone intermediates
  申请人：Bristol-Myers Company

  公开号：US04272437A1

  公开（公告）日：1981-06-09

  This invention relates to 2-substituted and 2,6-disubstituted penem compounds of the formula ##STR1## wherein Y is hydrogen, halo or certain organic substituents and X represents certain organic substituents. Also included in the invention are pharmaceutically acceptable salts of the above compounds and derivatives of the above compounds in which the carboxyl group at the 3-position is protected as by an easily removable ester protecting group. The compounds of the present invention are potent antibacterial agents or are of use as intermediates in the preparation of such agents.

  本发明涉及2-取代和2,6-二取代的青霉烯化合物，其公式为##STR1##，其中Y是氢、卤素或某些有机取代基，X代表某些有机取代基。发明还包括上述化合物的药用可接受盐和上述化合物的衍生物，其中3位的羧基被易于移除的酯保护基团所保护。本发明的化合物是强效的抗菌剂，或可用于制备此类药物的中间体。
• Efficient, One-Pot, BF3·OEt2-Mediated Synthesis of Substituted N-Aryl Lactams
  作者：Devdutt Chaturvedi、Amit Chaturvedi、Nisha Mishra、Virendra Mishra

  DOI：10.1055/s-0032-1317326

  日期：——

  A quick, efficient, one-pot, BF3·OEt2-mediated synthesis of substituted N-aryl lactams in good to excellent yields by reaction of various substituted arenes with a variety of ω-azido alkanoic acid chlorides at room temperature is reported.

  报道了一种快速、高效、一锅法、BF3·OEt2 介导的取代 N-芳基内酰胺合成，通过各种取代的芳烃与各种 ω-叠氮基链烷酰氯在室温下反应，收率良好。
• High-throughput synthesis of azide libraries suitable for direct “click” chemistry and in situ screening
  作者：Rajavel Srinivasan、Lay Pheng Tan、Hao Wu、Peng-Yu Yang、Karunakaran A. Kalesh、Shao Q. Yao

  DOI：10.1039/b902338k

  日期：——

  building blocks (key components in click chemistry). We report herein a highly robust and efficient strategy for high-throughput synthesis of a 325-member azide library. The method is highlighted by its simplicity and product purity. The utility of the library is demonstrated with the subsequent “click” synthesis of the corresponding bidentate inhibitors against PTP1B.

  当前药物发现中的关键挑战是开发高通量（HT）合适的化学反应，该反应可快速合成酶抑制剂的各种化学文库。叠氮化物和炔烃之间的Cu（I）催化的1,3-偶极环加成反应，称为“点击化学”，是近年来受到最广泛关注的一种方法。尽管它广受欢迎，但仍然缺乏可靠而有效的化学策略，这些策略无法访问各种包含叠氮化物的结构单元（点击化学中的关键成分）的库。我们在这里报告了一个高健壮和高效的策略，可用于325个成员的叠氮化物文库的高通量合成。该方法以其简单性和产品纯度而著称。
• Synthesis and In vitro activities of a spacer-containing glycophospholipid ligand of a lipopolysaccharide receptor involved in endotoxin tolerance
  作者：Daniel Charon、Michelle Mondange、Jean-François Pons、Karine Le Blay、Richard Chaby

  DOI：10.1016/s0968-0896(98)00027-3

  日期：1998.6

  with tetrabenzyl pyrophosphate. Hydrogenation on a Pd on carbon catalyst permitted the isolation of 6-(6-aminohexanoyl)-2,3-dideoxy-2,3-di-[(R)-3-hydroxy-tetradecanamido ] -alpha-D-glucopyranose 1,4-diphosphate (PPDm2-B). In mouse macrophages, PPDm2-B enhanced the lipopolysaccharide (LPS)-dependent secretion of tumor necrosis factor alpha (TNF-alpha), and inhibited the LPS-induced desensitization of these

  由N，N'-酰化和双磷酸化的2,3-二脱氧-2,3-二氨基-D-葡萄糖的衍生物组成的糖脂，在碳6处带有6-氨基己酰基侧链作为间隔臂（PPDm2-B），已经合成了其并评估了其对鼠巨噬细胞的作用。合成从2,3-二氨基-D-葡萄糖开始，这基本上是通过已知程序从葡糖胺获得的，因为尝试使用另一种已知前体（3-硝基糖苷）会导致意想不到的结果。用（D）-3-苄氧基肉豆蔻酸的羟基琥珀酰亚胺酯进行选择性N-酰化，然后通过6-叠氮基丙烯酰氯酯化唯一的伯羟基官能团，并通过用四苄基焦磷酸酯处理将所得的1,4-二醇磷酸化。在碳催化剂上的钯上氢化可分离出6-（6-氨基己基）-2，3-二脱氧-2，3-二-[（R）-3-羟基-十四烷酰胺基]-α-D-吡喃葡萄糖1,4-二磷酸酯（PPDm2-B）。在小鼠巨噬细胞中，PPDm2-B增强了肿瘤坏死因子α（TNF-α）的脂多糖（LPS）依赖性分泌，并抑制了LPS诱导的这些细胞脱敏