methyl 5-(4,9-dimethoxy-1-oxo-1H-dibenzo[b,f]cyclopropa[d]azocin-6(7H)-yl)-5-oxopentanoate | 1616955-33-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 5-(4,9-dimethoxy-1-oxo-1H-dibenzo[b,f]cyclopropa[d]azocin-6(7H)-yl)-5-oxopentanoate
• 英文别名: Methyl 5-(8,15-dimethoxy-3-oxo-11-azatetracyclo[11.4.0.02,4.05,10]heptadeca-1(13),2(4),5(10),6,8,14,16-heptaen-11-yl)-5-oxopentanoate；methyl 5-(8,15-dimethoxy-3-oxo-11-azatetracyclo[11.4.0.02,4.05,10]heptadeca-1(13),2(4),5(10),6,8,14,16-heptaen-11-yl)-5-oxopentanoate
• CAS: 1616955-33-9
• 化学式: C₂₄H₂₃NO₆
• 分子量: 421.45
• InChiKey: WMYQSTBXKNPQPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 5-(4,9-dimethoxy-1-oxo-1H-dibenzo[b,f]cyclopropa[d]azocin-6(7H)-yl)-5-oxopentanoate 以 乙腈 为溶剂， 反应 1.08h， 以35%的产率得到methyl 5-(3,8-dimethoxydidehydrodibenzo[b,f]azocin-5(6H)-yl)-5-oxopentanoate
  参考文献：
  名称：

  Synthesis of DIBAC analogues with excellent SPAAC rate constants

  摘要：

  四种新的DIBAC类似物显示出优秀的SPAAC速率常数，使它们与目前已知最快的环辛烯相媲美。

  DOI：

  10.1039/c4ob00694a
• 作为产物：
  描述：

  间氨基苯甲醚 在 aluminum (III) chloride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 23.08h， 生成 methyl 5-(4,9-dimethoxy-1-oxo-1H-dibenzo[b,f]cyclopropa[d]azocin-6(7H)-yl)-5-oxopentanoate
  参考文献：
  名称：

  Synthesis of DIBAC analogues with excellent SPAAC rate constants

  摘要：

  四种新的DIBAC类似物显示出优秀的SPAAC速率常数，使它们与目前已知最快的环辛烯相媲美。

  DOI：

  10.1039/c4ob00694a

文献信息

• [EN] HYDROPHILIC AZADIBENZOCYCLOOCTYNE DERIVATIVES AND METAL-FREE CLICK REACTIONS WITH THESE HYDROPHILIC AZADIBENZOCYCLOOCTYNE DERIVATIVES<br/>[FR] DÉRIVÉS D'AZADIBENZOCYCLOOCTYNE HYDROPHILES ET RÉACTIONS PAR CHIMIE-CLICK EXEMPTES DE MÉTAL AVEC CES DÉRIVÉS D'AZADIBENZOCYCLOOCTYNE HYDROPHILES
  申请人：[en]F. HOFFMANN-LA ROCHE AG

  公开号：WO2023083895A1

  公开（公告）日：2023-05-19

  The invention relates in a first aspect to an azadibenzocyclooctyne derivative according to formula (I) or a salt thereof having specific substituents at the benzo rings of the DIBAC structure and having specific substituents connected to the nitrogen atom of the DIBAC structure. A second aspect of the invention is directed to a conjugate of formula (II), wherein a substituent R6is connected to the N atom of the 8 membered ring of the DIBAC structure via a linker structure –C(=O)-[L]n-Z-. A third aspect of the invention relates to a method for the modification of a target molecule, wherein a conjugate according to the second aspect is reacted with a target molecule comprising a 1,3-dipole group or a 1,3-(hetero)diene group. In a fourth aspect, the invention is directed to the use of the conjugate according to the second aspect for bioorthogonal labeling and/or modification of a target molecule. A fifth aspect of the invention relates to a modified target molecule comprising the reaction product of a conjugate according to the second aspect and a target molecule comprising a 1,3-dipole group or a 1,3-(hetero)diene group, obtained or obtainable from the method of the third aspect. In a sixth aspect, the invention is related to a kit comprising a modified target molecule according to the fifth aspect as detector reagent and a suitable capture reagent.