1',3',3'-trimethyl-5',6-dinitro-8-chloromethyl-spiro(2H-1-benzopyran-2,2'-indoline) | 1132779-27-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1',3',3'-trimethyl-5',6-dinitro-8-chloromethyl-spiro(2H-1-benzopyran-2,2'-indoline)
• 英文别名: 8-(Chloromethyl)-1',3',3'-trimethyl-5',6-dinitrospiro[chromene-2,2'-indole]；8-(chloromethyl)-1',3',3'-trimethyl-5',6-dinitrospiro[chromene-2,2'-indole]
• CAS: 1132779-27-1
• 化学式: C₂₀H₁₈ClN₃O₅
• 分子量: 415.833
• InChiKey: UUAPORUJGYZQCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1',3',3'-trimethyl-5',6-dinitro-8-chloromethyl-spiro(2H-1-benzopyran-2,2'-indoline) 在 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以96%的产率得到1',3',3'-trimethyl-5',6-dinitro-8-iodomethyl-spiro(2H-1-benzopyran-2,2'-indoline)
  参考文献：
  名称：

  Synthesis and characterization of a redox- and light-sensitive MRI contrast agent

  摘要：

  A redox- and light-sensitive, T-1-weighted magnetic resonance imaging (MRI) contrast agent, which tethers a spiropyran (SP)/merocyanine (MC) motif to a Gd-DO3A moiety was synthesized and characterized. When in the dark, the probe is in its MC form, which has an r(1) relaxivity of 2.51 m M (1)s (1) (60 MHz, 37 C). After irradiation with visible light or mixing with NADH, the probe experiences an isomerization and the r(1) relaxivity decreased 18% and 26%, respectively. Additionally, the signal intensity in MRI showed an observable decrease after the compound was mixed with NADH. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.020
• 作为产物：
  描述：

  1,3,3-三甲基-2-亚甲基-5-硝基吲哚 、 3-氯甲基-5-硝基水杨醛 以 四氢呋喃 为溶剂， 反应 24.0h， 以49%的产率得到1',3',3'-trimethyl-5',6-dinitro-8-chloromethyl-spiro(2H-1-benzopyran-2,2'-indoline)
  参考文献：
  名称：

  Synthesis and characterization of a redox- and light-sensitive MRI contrast agent

  摘要：

  A redox- and light-sensitive, T-1-weighted magnetic resonance imaging (MRI) contrast agent, which tethers a spiropyran (SP)/merocyanine (MC) motif to a Gd-DO3A moiety was synthesized and characterized. When in the dark, the probe is in its MC form, which has an r(1) relaxivity of 2.51 m M (1)s (1) (60 MHz, 37 C). After irradiation with visible light or mixing with NADH, the probe experiences an isomerization and the r(1) relaxivity decreased 18% and 26%, respectively. Additionally, the signal intensity in MRI showed an observable decrease after the compound was mixed with NADH. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.12.020

文献信息

• Synthesis and characterization of a redox- and light-sensitive MRI contrast agent
  作者：Chuqiao Tu、Elizabeth A. Osborne、Angelique Y. Louie

  DOI：10.1016/j.tet.2008.12.020

  日期：2009.2

  A redox- and light-sensitive, T-1-weighted magnetic resonance imaging (MRI) contrast agent, which tethers a spiropyran (SP)/merocyanine (MC) motif to a Gd-DO3A moiety was synthesized and characterized. When in the dark, the probe is in its MC form, which has an r(1) relaxivity of 2.51 m M (1)s (1) (60 MHz, 37 C). After irradiation with visible light or mixing with NADH, the probe experiences an isomerization and the r(1) relaxivity decreased 18% and 26%, respectively. Additionally, the signal intensity in MRI showed an observable decrease after the compound was mixed with NADH. (C) 2008 Elsevier Ltd. All rights reserved.