2,3,3-trimethylindolino(1,2-b)oxazine | 140451-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2,3,3-trimethylindolino(1,2-b)oxazine
• 英文别名: 10,10,10a-trimethyl-3,4,10,10a-tetrahydro-2H-[1,3]oxazino[3,2-a]indole；10,10,10a-trimethyl-3,4-dihydro-2H-[1,3]oxazino[3,2-a]indole
• CAS: 140451-72-5
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: VWFLHUSSSXMNIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-羟基-6-甲基吡啶-2-羧醛 、 2,3,3-trimethylindolino(1,2-b)oxazine 以 乙醇 为溶剂， 反应 5.0h， 以38%的产率得到3-(3,3,6'-Trimethylspiro[indole-2,2'-pyrano[3,2-b]pyridine]-1-yl)propan-1-ol
  参考文献：
  名称：

  Ultrafast Dynamics of a Spiropyran in Water

  摘要：

  The reversible switching of a water-soluble spiropyran compound is recorded over 1 ns by means of femtosecond vis-pump/vis- and IR-probe spectroscopy under aqueous conditions. Our investigations reveal that the photochemical conversion from the closed spiropyran to the open merocyanine takes 1.6 ps whereas the reversed photoreaction is accomplished within 25 ps. The combination of time-resolved and steady-state observations allows us to reveal central parts of the reaction pathway leading to either form. The enhanced water solubility, its fast and efficient switching behavior, and its stability against hydrolysis over a time range of several weeks make this compound an attractive and versatile tool for biological applications.

  DOI：

  10.1021/ja304395k
• 作为产物：
  描述：

  1-(3-hydroxypropyl)-2,3,3-trimethyl-3H-indolium iodide 在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以43%的产率得到2,3,3-trimethylindolino(1,2-b)oxazine
  参考文献：
  名称：

  Synthesis of DNA with Spirobenzopyran as an Internal Covalent Modification

  摘要：

  通过两种不同的合成策略，光致变色螺吡喃被作为内部修饰引入到寡核苷酸中：第一条路线是将螺吡喃膦酰胺合成作为DNA构建模块，而第二条路线则采用了后合成“点击”型连接反应。在双链DNA中，色素的光诱导开环未能实现。

  DOI：

  10.1055/s-0029-1219924

文献信息

• Bartnik, Romuald; Mloston, Grzegorz; Lesniak, Stanislaw, Polish Journal of Chemistry, 1991, vol. 65, # 11, p. 1957 - 1961
  作者：Bartnik, Romuald、Mloston, Grzegorz、Lesniak, Stanislaw

  DOI：——

  日期：——
• SHACHKUS, A. A., NAUCH. TR. VUZOV LITSSR. XIMIYA I XIM. TEXNOL., 30,(1988) S. 79-83
  作者：SHACHKUS, A. A.

  DOI：——

  日期：——
• Synthesis of DNA with Spirobenzopyran as an Internal Covalent Modification
  作者：Hans-Achim Wagenknecht、Christoph Beyer

  DOI：10.1055/s-0029-1219924

  日期：2010.6

  The photochromic spirobenzopyran was incorporated as an internal modification into oligonucleotides by two different synthetic strategies: For the first route the spiropyran phosphoramidite was synthesized as a DNA building block, whereas for the second route the postsynthetic ‘click’-type ligation was applied. Photo­induced ring opening of the chromophore could not be achieved in duplex DNA.

  通过两种不同的合成策略，光致变色螺吡喃被作为内部修饰引入到寡核苷酸中：第一条路线是将螺吡喃膦酰胺合成作为DNA构建模块，而第二条路线则采用了后合成“点击”型连接反应。在双链DNA中，色素的光诱导开环未能实现。
• Ultrafast Dynamics of a Spiropyran in Water
  作者：Jörg Kohl-Landgraf、Markus Braun、Cem Özçoban、Diana P. N. Gonçalves、Alexander Heckel、Josef Wachtveitl

  DOI：10.1021/ja304395k

  日期：2012.8.29

  The reversible switching of a water-soluble spiropyran compound is recorded over 1 ns by means of femtosecond vis-pump/vis- and IR-probe spectroscopy under aqueous conditions. Our investigations reveal that the photochemical conversion from the closed spiropyran to the open merocyanine takes 1.6 ps whereas the reversed photoreaction is accomplished within 25 ps. The combination of time-resolved and steady-state observations allows us to reveal central parts of the reaction pathway leading to either form. The enhanced water solubility, its fast and efficient switching behavior, and its stability against hydrolysis over a time range of several weeks make this compound an attractive and versatile tool for biological applications.