N-acryloyl-N'-trifluoroacetyl-1,6-diaminohexane | 124022-79-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acryloyl-N'-trifluoroacetyl-1,6-diaminohexane
• 英文别名: 6-acryloyl-N'-trifluoroacetyl-1,6-diaminohexane；N-(6-(2,2,2-trifluoroacetamido)hexyl)acrylamide；N-[6-[(2,2,2-trifluoroacetyl)amino]hexyl]prop-2-enamide
• CAS: 124022-79-3
• 化学式: C₁₁H₁₇F₃N₂O₂
• 分子量: 266.263
• InChiKey: PPSMJZHSDCFBJH-UHFFFAOYSA-N

物化性质

• 沸点：
  419.1±45.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-acryloyl-N'-trifluoroacetyl-1,6-diaminohexane 在 palladium diacetate 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 15.0h， 生成 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-{N-[6-(trifluoroacetylamino)-hexyl]-acrylamide}-uracil
  参考文献：
  名称：

  SYNTHESIS OF 5-ALKENYLATED D4T ANALOGUES VIA THE Pd-CATALYZED CROSS-COUPLING REACTION

  摘要：

  The target compounds 5-[N-(6-amino-hexyl)-acrylamide]-2 ' ,3 ' -didehydro-2 ' ,3 ' -dideoxy-uridine (12) and 5-{N-[5-(methoxycarbonyl)-pentyl]acrylamide}-2 ' ,3 ' -didehydro-2',3 ' -dideoxy-uridine (15) were prepared by the palladium acetate-triphenylphosphine-catalyzed reaction of the 5 ' -O-acetyl-5-iodo-d4T analogue (3). These compounds 12 and 15 can be used to prepare nucleotide probes carrying fluorescent labels and were nevertheless screened for their anti-HIV activity. The biological data demonstrated that none of them were active against HIV-1.

  DOI：

  10.1081/ncn-100105902
• 作为产物：
  描述：

  1,6-己二胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 N-acryloyl-N'-trifluoroacetyl-1,6-diaminohexane
  参考文献：
  名称：

  SYNTHESIS OF 5-ALKENYLATED D4T ANALOGUES VIA THE Pd-CATALYZED CROSS-COUPLING REACTION

  摘要：

  The target compounds 5-[N-(6-amino-hexyl)-acrylamide]-2 ' ,3 ' -didehydro-2 ' ,3 ' -dideoxy-uridine (12) and 5-{N-[5-(methoxycarbonyl)-pentyl]acrylamide}-2 ' ,3 ' -didehydro-2',3 ' -dideoxy-uridine (15) were prepared by the palladium acetate-triphenylphosphine-catalyzed reaction of the 5 ' -O-acetyl-5-iodo-d4T analogue (3). These compounds 12 and 15 can be used to prepare nucleotide probes carrying fluorescent labels and were nevertheless screened for their anti-HIV activity. The biological data demonstrated that none of them were active against HIV-1.

  DOI：

  10.1081/ncn-100105902

文献信息

• Pd–imidate complexes as recyclable catalysts for the synthesis of C5-alkenylated pyrimidine nucleosides via Heck cross-coupling reaction
  作者：Ajaykumar V. Ardhapure、Yogesh S. Sanghvi、Anant R. Kapdi、Joaquín García、Gregorio Sanchez、Pedro Lozano、J. Luis Serrano

  DOI：10.1039/c5ra01461a

  日期：——

  Pd–imidate complexes as recyclable catalysts for Heck alkenylation of pyrimidine nucleosides. Pd–imidate complexes have been employed as efficient catalysts for the Heck alkenylation of unprotected 5-iodo-2′-deoxyuridine in acetonitrile.

  Pd-咪唑酮配合物作为可回收催化剂用于吡咯嘧啶核苷的Heck烯基化反应。Pd-咪唑酮配合物已被应用作为在乙腈中对未保护的5-碘-2'-脱氧尿嘧啶进行Heck烯基化反应的高效催化剂。
• Scale-Up of a Heck Alkenylation Reaction: Application to the Synthesis of an Amino-Modifier Nucleoside ‘Ruth Linker’
  作者：Anant R. Kapdi、Shatrughn Bhilare、Santosh Kori、Harshita Shet、Gundapally Balaram、Koosam Mahendar、Yogesh S. Sanghvi

  DOI：10.1055/s-0040-1707260

  日期：2020.12

  involving a palladium-catalyzed Heck alkenylation is described. The synthesis has been optimized with a goal of low catalyst concentration, column-free isolation, high product purity, reproducibility, and shorter reaction time. The scalability and utility of the process have been demonstrated successfully on a 100 g scale (starting material). Additionally, for scale-up of the Heck alkenylation protocol, 7-phospha-1

  致力于纪念杰里·林恩·露丝（Jerry Lynn Ruth），他首先展示了该分子在DNA标记中的用途 抽象 露丝接头是C5嘧啶修饰的核苷类似物，广泛用于在合成寡核苷酸中掺入伯胺。对非放射性标记，生物分子检测以及COVID-19测试试剂盒的组装的需求不断增长，引发了对Ruth接头规模扩大的需求。在本文中，描述了涉及钯催化的Heck烯基化的有效方案。为了达到低催化剂浓度，无柱分离，高产物纯度，可重复性和缩短反应时间的目标，对合成进行了优化。该方法的可扩展性和实用性已在100 g规模（原材料）上得到了成功证明。此外，为了扩大Heck烯基化协议，7-phospha-1,3， 出版历史 收到：2020年6月6日 修订后接受：2020年8月1日 发布日期： 2020年9月8日（在线） ©2020年。Thieme。版权所有 Georg Thieme Verlag KGRüdigerstraße14，70469斯图加特，德国
• Modulation of the Electronic Properties of Non-innocent (E,E)-Dibenzylideneacetone for Palladium(0)-Mediated Heck Alkenylation of 5-Iodo-2′-deoxyuridine and Scale-Up Studies
  作者：Anant Kapdi、Ajay Ardhapure、Yogesh Sanghvi

  DOI：10.1055/s-0034-1379962

  日期：——

  Subtle modulation of the electronic properties of the dibenzylideneacetone (dba) ligand allows the development of an efficient protocol for the Heck alkenylation of 5-iodo-2-deoxyuridine. This protocol enables the large-scale synthesis of commercially important nucleoside building blocks. The isolation of one key molecule was accomplished under column-free conditions on a 10-gram scale.
• SYNTHESIS OF 5-ALKENYLATED D4T ANALOGUES VIA THE Pd-CATALYZED CROSS-COUPLING REACTION
  作者：A. Ciurea、C. Fossey、S. Benzaria、D. Gavriliu、Z. Delbederi、B. Lelong、D. Ladurée、A. M. Aubertin、A. Kirn

  DOI：10.1081/ncn-100105902

  日期：2001.9.30

  The target compounds 5-[N-(6-amino-hexyl)-acrylamide]-2 ' ,3 ' -didehydro-2 ' ,3 ' -dideoxy-uridine (12) and 5-N-[5-(methoxycarbonyl)-pentyl]acrylamide}-2 ' ,3 ' -didehydro-2',3 ' -dideoxy-uridine (15) were prepared by the palladium acetate-triphenylphosphine-catalyzed reaction of the 5 ' -O-acetyl-5-iodo-d4T analogue (3). These compounds 12 and 15 can be used to prepare nucleotide probes carrying fluorescent labels and were nevertheless screened for their anti-HIV activity. The biological data demonstrated that none of them were active against HIV-1.