carbonic acid 7,8-didehydro-1,2:5,6-dibenzocyclooctene-3-yl ester, 6'-(2-cyanoethoxy-N,N-diisopropylamino)phosphine-1'-amide | 1257084-31-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: carbonic acid 7,8-didehydro-1,2:5,6-dibenzocyclooctene-3-yl ester, 6'-(2-cyanoethoxy-N,N-diisopropylamino)phosphine-1'-amide
• 英文别名: 2-tricyclo[10.4.0.04,9]hexadeca-1(16),4,6,8,12,14-hexaen-10-ynyl N-[6-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyhexyl]carbamate
• CAS: 1257084-31-3
• 化学式: C₃₂H₄₂N₃O₄P
• 分子量: 563.677
• InChiKey: MWEGZIINPUELQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  carbonic acid 7,8-didehydro-1,2:5,6-dibenzocyclooctene-3-yl ester ((6'-hydroxy)hexyl)-1'-amide 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以98%的产率得到carbonic acid 7,8-didehydro-1,2:5,6-dibenzocyclooctene-3-yl ester, 6'-(2-cyanoethoxy-N,N-diisopropylamino)phosphine-1'-amide
  参考文献：
  名称：

  Synthesis of Oligoribonucleic Acid Conjugates Using a Cyclooctyne Phosphoramidite

  摘要：

  The conjugation of a ribonucleic acid 16-mer with the cationic amphiphilic peptide penetratin and an anionic hyaluronan tetrasaccharide by means of Cu-free "click" chemistry is reported. The alkyne-functionalized 16-mer was prepared by automated solid-phase synthesis, using a newly developed strained cyclooctyne phosphoramidite in the final coupling. Cycloaddition of the alkyne functionalized RNA to the azide containing biomolecules led to a clean conversion into the corresponding nucleic acid conjugates.

  DOI：

  10.1021/ol102357u

文献信息

• Synthesis of Oligoribonucleic Acid Conjugates Using a Cyclooctyne Phosphoramidite
  作者：Pieter van Delft、Nico J. Meeuwenoord、Sascha Hoogendoorn、Jasper Dinkelaar、Herman S. Overkleeft、Gijsbert A. van der Marel、Dmitri V. Filippov

  DOI：10.1021/ol102357u

  日期：2010.12.3

  The conjugation of a ribonucleic acid 16-mer with the cationic amphiphilic peptide penetratin and an anionic hyaluronan tetrasaccharide by means of Cu-free "click" chemistry is reported. The alkyne-functionalized 16-mer was prepared by automated solid-phase synthesis, using a newly developed strained cyclooctyne phosphoramidite in the final coupling. Cycloaddition of the alkyne functionalized RNA to the azide containing biomolecules led to a clean conversion into the corresponding nucleic acid conjugates.