(E)-7-azidohept-2-en-1-ol | 1234215-51-0

• 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: (E)-7-azidohept-2-en-1-ol
• 英文别名: 7-azido-hept-2-en-1-ol
• CAS: 1234215-51-0
• 化学式: C₇H₁₃N₃O
• 分子量: 155.2
• InChiKey: XEUFJDJFVXRFIO-HWKANZROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-7-azidohept-2-en-1-ol 在 哌啶 、 吡啶 、 2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 、 四溴化碳 、 四丁基氟化铵 、 碳酸氢钠 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 aq. phosphate buffer 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.18h， 生成
  参考文献：
  名称：

  Synthesis of 3′-O-fluorescently mono-modified reversible terminators and their uses in sequencing-by-synthesis

  摘要：

  Next-generation sequencing (NGS) technologies recently developed are now used for study of genomes from various organisms. Sequencing-by-synthesis (SBS) is a key strategy in the NGS. The SBS uses nucleotides so-called dual-modified reversible terminators (DRTs) in which bases are labeled with fluorophores and 3'-OH is protected with a reversibly cleavable chemical group, respectively. In this study, we examined the possibility of performing SBS with mono-modified reversible terminators (MRTs), in which the reversible blocking group on the 3'-OH plays a dual role as a fluorescent signal report as well as a chemical protection. We studied cyclic reversible termination by using two MRTs (dA and dT), wherein the modifications were two different fluorophores and cleavable to regenerate a free 3'-OH. We here demonstrated that SBS could be achieved with incorporation of MRTs by a DNA polymerase and correct base-calls based on the two different colors from the fluorophores. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.040
• 作为产物：
  描述：

  5-((叔丁基二甲基甲硅烷基)氧基)戊醛 在 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 36.0h， 生成 (E)-7-azidohept-2-en-1-ol
  参考文献：
  名称：

  Synthesis of 3′-O-fluorescently mono-modified reversible terminators and their uses in sequencing-by-synthesis

  摘要：

  Next-generation sequencing (NGS) technologies recently developed are now used for study of genomes from various organisms. Sequencing-by-synthesis (SBS) is a key strategy in the NGS. The SBS uses nucleotides so-called dual-modified reversible terminators (DRTs) in which bases are labeled with fluorophores and 3'-OH is protected with a reversibly cleavable chemical group, respectively. In this study, we examined the possibility of performing SBS with mono-modified reversible terminators (MRTs), in which the reversible blocking group on the 3'-OH plays a dual role as a fluorescent signal report as well as a chemical protection. We studied cyclic reversible termination by using two MRTs (dA and dT), wherein the modifications were two different fluorophores and cleavable to regenerate a free 3'-OH. We here demonstrated that SBS could be achieved with incorporation of MRTs by a DNA polymerase and correct base-calls based on the two different colors from the fluorophores. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.040

文献信息

• Catalytic S_N2′-Selective Substitution of Allylic Chlorides With Arylboronic Esters
  作者：Aaron M. Whittaker、Richard P. Rucker、Gojko Lalic

  DOI：10.1021/ol101171v

  日期：2010.7.16

  A copper-catalyzed SN2′-selective arylation of allylic chlorides has been achieved using arylboronic esters as nucleophiles. Arylation products were obtained in high yield with a variety of allylic chlorides and arylboronic esters in the presence of a wide range of functional groups. A mechanism is proposed on the basis of the results of stoichiometric experiments and the isolation of the proposed

  使用芳基硼酸酯作为亲核试剂，已经实现了铜催化的烯丙基氯化物的S N 2'选择性芳基化。在各种官能团存在的情况下，可以使用多种烯丙基氯化物和芳基硼​​酸酯以高收率获得丙烯酸化产物。根据化学计量的实验结果和所提出的中间体的分离，提出了一种机理。
• Chemoenzymatic Late‐Stage Modifications Enable Downstream Click‐Mediated Fluorescent Tagging of Peptides
  作者：Alessandro Colombano、Luca Dalponte、Sergio Dall'Angelo、Claudia Clemente、Mohannad Idress、Ahmad Ghazal、Wael E. Houssen

  DOI：10.1002/anie.202215979

  日期：——

  suitable for copper-catalyzed azide-alkyne cycloaddition, metathesis, and inverse-electron-demand Diels-Alder (IEDDA) reactions. A 10-mer tryptophan-containing macrocyclic peptide was tailored by AcyF, and the resulting modified peptide was successfully labelled with a tetrazine–fluorescein conjugate by IEDDA.

  用 22 种非天然焦磷酸盐筛选了 N1-色氨酸异戊二烯基转移酶 AcyF 的混杂性，这些焦磷酸盐表现出适合铜催化叠氮-炔环加成、复分解和逆电子需求 Diels-Alder (IEDDA) 反应的反应基团。 AcyF 定制了含有色氨酸的 10 聚体大环肽，并通过 IEDDA 成功地用四嗪-荧光素缀合物标记了所得修饰肽。
• Synthesis of 3′-O-fluorescently mono-modified reversible terminators and their uses in sequencing-by-synthesis
  作者：Da-Rae Kim、Taek-Soo Kim、Eunsun Kim、Sun-Joon Min、Dongyun Shin、Dae-Ro Ahn

  DOI：10.1016/j.bmcl.2013.11.040

  日期：2014.1

  Next-generation sequencing (NGS) technologies recently developed are now used for study of genomes from various organisms. Sequencing-by-synthesis (SBS) is a key strategy in the NGS. The SBS uses nucleotides so-called dual-modified reversible terminators (DRTs) in which bases are labeled with fluorophores and 3'-OH is protected with a reversibly cleavable chemical group, respectively. In this study, we examined the possibility of performing SBS with mono-modified reversible terminators (MRTs), in which the reversible blocking group on the 3'-OH plays a dual role as a fluorescent signal report as well as a chemical protection. We studied cyclic reversible termination by using two MRTs (dA and dT), wherein the modifications were two different fluorophores and cleavable to regenerate a free 3'-OH. We here demonstrated that SBS could be achieved with incorporation of MRTs by a DNA polymerase and correct base-calls based on the two different colors from the fluorophores. (C) 2013 Elsevier Ltd. All rights reserved.