6-[(2R,5R)-5-(hydroxymethyl)-4-oxooxolan-2-yl]-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraen-4-one | 213481-07-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 6-[(2R,5R)-5-(hydroxymethyl)-4-oxooxolan-2-yl]-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraen-4-one
• CAS: 213481-07-3
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: LHNUESRMULOCRY-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-[(2R,5R)-5-(hydroxymethyl)-4-oxooxolan-2-yl]-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraen-4-one 在 吡啶 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 乙腈 为溶剂， 反应 3.17h， 生成 8-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2,3,5,6-tetrahydro-1H,4H-11-oxa-3a-aza-benzo[de]anthracen-10-one
  参考文献：
  名称：

  Coumarin base-pair replacement as a fluorescent probe of ultrafast DNA dynamics

  摘要：

  The design and synthesis of a novel coumarin C-riboside are described, and is based on the well-known photoprobe Coumarin 102. A diastereofacial selective Heck coupling between a furanoid glycal and a coumarin triflate provided a method for glycoside formation. The coumarin C-glycoside was incorporated synthetically into DNA oligomers, and was used to probe ultrafast dynamics of duplex DNA using time-resolved Stokes shift methods. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.12.096
• 作为产物：
  描述：

  4-羟基-6H-香豆素 在 palladium diacetate 1,3-双(二苯基膦)丙烷 、 碳酸氢钠 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 6-[(2R,5R)-5-(hydroxymethyl)-4-oxooxolan-2-yl]-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1(17),2(7),5,8-tetraen-4-one
  参考文献：
  名称：

  Coumarin base-pair replacement as a fluorescent probe of ultrafast DNA dynamics

  摘要：

  The design and synthesis of a novel coumarin C-riboside are described, and is based on the well-known photoprobe Coumarin 102. A diastereofacial selective Heck coupling between a furanoid glycal and a coumarin triflate provided a method for glycoside formation. The coumarin C-glycoside was incorporated synthetically into DNA oligomers, and was used to probe ultrafast dynamics of duplex DNA using time-resolved Stokes shift methods. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2006.12.096

文献信息

• Synthesis of a Novel Coumarin C-Riboside as a Photophysical Probe of Oligonucleotide Dynamics
  作者：Robert S. Coleman、Mihaela L. Madaras

  DOI：10.1021/jo980478+

  日期：1998.8.1
• Coumarin base-pair replacement as a fluorescent probe of ultrafast DNA dynamics
  作者：Robert S. Coleman、Mark A. Berg、Catherine J. Murphy

  DOI：10.1016/j.tet.2006.12.096

  日期：2007.4

  The design and synthesis of a novel coumarin C-riboside are described, and is based on the well-known photoprobe Coumarin 102. A diastereofacial selective Heck coupling between a furanoid glycal and a coumarin triflate provided a method for glycoside formation. The coumarin C-glycoside was incorporated synthetically into DNA oligomers, and was used to probe ultrafast dynamics of duplex DNA using time-resolved Stokes shift methods. (c) 2007 Published by Elsevier Ltd.