N-(prop-2-yn-1-yl)dodecanamide | 114932-69-3

• 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-(prop-2-yn-1-yl)dodecanamide
• 英文别名: N-prop-2-ynyldodecanamide
• CAS: 114932-69-3
• 化学式: C₁₅H₂₇NO
• 分子量: 237.385
• InChiKey: ZTZIGLQEDTZAKA-UHFFFAOYSA-N

物化性质

• 沸点：
  376.9±25.0 °C(Predicted)
• 密度：
  0.892±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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-(prop-2-yn-1-yl)dodecanamide 在 zinc trifluoromethanesulfonate 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 甲苯 、 苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Zn催化的BocNHNH 2炔丙基酰胺的氢肼化作用：1,2,4-三嗪核心†的新入口†

  摘要：

  出乎意料的是，在Zn（OTf）2催化下，用BocNHNH 2将各种炔丙基酰胺进行氢肼化，出乎意料的是，二氢-1,2,4-三嗪失去了保护基。初始产品可以用K 3 [Fe（CN）6 ]有效地原位加香。这为医学上重要的1,2,4-三嗪核心提供了新的机会。

  DOI：

  10.1039/c6ra12664b
• 作为产物：
  描述：

  月桂酰氯 、 炔丙胺 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到N-(prop-2-yn-1-yl)dodecanamide
  参考文献：
  名称：

  炔丙基酰胺在六氟异丙醇 (HFIP) 中的无过渡金属环异构化为恶唑

  摘要：

  开发了一种无过渡金属的炔丙基酰胺环异构化为恶唑的方法。该反应利用在六氟异丙醇 (HFIP) 中原位生成的氯化氢。在实验设计优化的帮助下，广泛的底物被转化为所需的恶唑。该方法可以在没有副反应的情况下形成产物，从而无需进行大量的后处理和纯化。

  DOI：

  10.1002/adsc.202200559

文献信息

• The High-Throughput Synthesis and Phase Characterisation of Amphiphiles: A Sweet Case Study
  作者：George C. Feast、Oliver E. Hutt、Xavier Mulet、Charlotte E. Conn、Calum J. Drummond、G. Paul Savage

  DOI：10.1002/chem.201303514

  日期：2014.3.3

  A new method for the discovery of amphiphiles by using high‐throughput (HT) methods to synthesise and characterise a library of galactose‐ and glucose‐containing amphiphilic compounds is presented. The copper‐catalysed azide–alkyne cycloaddition (CuAAC) “click” reaction between azide‐tethered simple sugars and alkyne‐substituted hydrophobic tails was employed to synthesise a library of compounds with

  提出了一种通过使用高通量（HT）方法合成和表征含有半乳糖和葡萄糖的两亲化合物文库的发现两亲化合物的新方法。用铜催化的叠氮化物-炔烃环加成（CuAAC）叠氮化物连接的单糖和炔烃取代的疏水尾巴之间的“点击”反应以24小瓶阵列格式合成了具有系统性链长和不饱和度变化的化合物库。通过使用同步加速器小角度X射线散射（SSAXS），以HT方式表征了液晶相的行为。讨论了观察到的关于链参数的结构变化，包括链长和不饱和度，以及水合效应和首基之间的氢键结合程度。我们的HT筛选方法的有效性通过重新合成短链葡萄糖两亲物来验证。对该化合物进行的单独相分析证实了许多溶致液晶相的存在。
• 2-Aminopyrimidine as a novel scaffold for biofilm modulation
  作者：Erick A. Lindsey、Roberta J. Worthington、Cristina Alcaraz、Christian Melander

  DOI：10.1039/c2ob06871k

  日期：——

  An efficient synthetic route to a series of substituted 2-aminopyrimidine (2-AP) derivatives has been developed. Subsequent biofilm screening has allowed comparison between the biological activity of these new derivatives and that of the 2-aminoimidazole class of anti-biofilm compounds. Several derivatives displayed the ability to modulate bacterial biofilm formation, exhibiting greater activity against Gram-positive strains than Gram-negative strains. Additionally some 2-aminopyrmidines were able to suppress MRSA resistance to conventional antibiotics.

  我们开发出了一系列取代的 2-氨基嘧啶（2-AP）衍生物的高效合成路线。随后的生物膜筛选将这些新衍生物的生物活性与 2-氨基咪唑类抗生物膜化合物的生物活性进行了比较。一些衍生物显示出调节细菌生物膜形成的能力，对革兰氏阳性菌株的活性高于对革兰氏阴性菌株的活性。此外，一些 2-aminopyrmidines 还能抑制 MRSA 对传统抗生素的耐药性。
• Bimetallic tandem catalysis-enabled enantioselective cycloisomerization/carbonyl–ene reaction for construction of 5-oxazoylmethyl α-silyl alcohol
  作者：Xinpeng Sang、Yuhao Mo、Shiya Li、Xiaohua Liu、Weidi Cao、Xiaoming Feng

  DOI：10.1039/d3sc01048a

  日期：——

  A bimetallic tandem catalysis-enabled enantioselective cycloisomerization/carbonyl–ene reaction was developed. The reaction proceeded well with a broad range of N-propargylamides and acylsilanes, affording the target chiral 5-oxazoylmethyl α-silyl alcohols in up to 95% yield and 99% ee under mild conditions. Importantly, this facile protocol was available for the late-stage modification of several

  开发了一种双金属串联催化的对映选择性环异构化/羰基-烯反应。该反应与多种N-炔丙基酰胺和酰基硅烷一起顺利进行，在温和条件下以高达 95% 的产率和 99% ee 得到目标手性 5-恶唑酰基甲基 α-硅醇。重要的是，这种简便的方案可用于几种生物活性分子的后期修饰。基于机理研究和控制实验，提出了可能的催化循环和过渡态来阐明反应过程和对映诱导。
• Synthesis and Biophysical Properties of C5-Functionalized LNA (Locked Nucleic Acid)
  作者：Pawan Kumar、Michael E. Østergaard、Bharat Baral、Brooke A. Anderson、Dale C. Guenther、Mamta Kaura、Daniel J. Raible、Pawan K. Sharma、Patrick J. Hrdlicka

  DOI：10.1021/jo500614a

  日期：2014.6.6

  Oligonucleotides modified with conformationally restricted nucleotides such as locked nucleic acid (LNA) monomers are used extensively in molecular biology and medicinal chemistry to modulate gene expression at the RNA level. Major efforts have been devoted to the design of LNA derivatives that induce even higher binding affinity and specificity, greater enzymatic stability, and more desirable pharmacokinetic profiles. Most of this work has focused on modifications of LNA's oxymethylene bridge. Here, we describe an alternative approach for modulation of the properties of LNA: i.e., through functionalization of LNA nucleobases. Twelve structurally diverse CS-functionalized LNA uridine (U) phosphoramidites were synthesized and incorporated into oligodeoxyribonucleotides (ONs), which were then characterized with respect to thermal denaturation, enzymatic stability, and fluorescence properties. ONs modified with monomers that are conjugated to small alkynes display significantly improved target affinity, binding specificity, and protection against 3'-exonucleases relative to regular LNA. In contrast, ONs modified with monomers that are conjugated to bulky hydrophobic alkynes display lower target affinity yet much greater 3'-exonuclease resistance. ONs modified with C5-fluorophore-functionalized LNA-U monomers enable fluorescent discrimination of targets with single nucleotide polymorphisms (SNPs). In concert, these properties render C5-functionalized LNA as a promising class of building blocks for RNA-targeting applications and nucleic acid diagnostics.
• CLEAR PERSONAL CARE FORMULATIONS CONTAINING QUATERNARY AMMONIUM COMPOUNDS AND OTHER NITROGEN-CONTAINING COMPOUNDS
  申请人：Goldschmidt Chemical Company

  公开号：EP1076554B1

  公开（公告）日：2004-10-13