Nitro-BIPS | 211505-94-1

• 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: Nitro-BIPS
• 英文别名: 3',3'-dimethyl-6-nitrospiro[2H-1-benzopyran-2,2'-[2H]indole]-1'(3'H)-propanol；3',3'-dimethyl-6-nitro-1'-[3-hydroxypropyl]spiro[2H-benzopyran-2,2'(3'H)-[1H]indole]；SP-1；3-(3',3'-Dimethyl-6-nitrospiro[chromene-2,2'-indole]-1'-yl)propan-1-ol
• CAS: 211505-94-1
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: NCSGLJXIGRXROJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Nitro-BIPS 、 对硝基苯基氯甲酸酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到
  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
• 作为产物：
  描述：

  6-[2-[1-(3-Hydroxypropyl)-3,3-dimethylindol-2-ylidene]ethylidene]-4-nitrocyclohexa-2,4-dien-1-one 以 甲醇 为溶剂， 生成 Nitro-BIPS
  参考文献：
  名称：

  CO₂ Triggering and Controlling Orthogonally Multiresponsive Photochromic Systems

  摘要：

  We report a new generic method of reversibly controlling the photochromism of spiropyrans. It was found that the photochromic effect of spiropyrans can be reversibly switched on and off by addition and removal of carbon dioxide (CO2) to spiropyran in alcohol solutions containing an amidine (i.e., DBU) that acts as a CO2 sensitizer. Spiropyrans are not photochromic in the presence of DBU but photochromic when CO2 is subsequently added to the solution. The CO2 is readily removed by inert gas bubbling, thus allowing facile activation and deactivation of the photochromic effect. Carbon dioxide, without the presence of the sensitizing amidine, had no effect on photochromism of the spiropyrans. Other photochromic dyes classes such as spirooxazines and chromenes are not affected by this CO2/DBU stimulus. As a result, orthogonal activation of mixtures of spirooxazines and spiropyrans was achieved to provide four color states (clear, yellow, green, and blue) by varying the combinations of the stimuli of UV, visible light, CO2, and CO2 depleted. This finding now permits the many applications using spiropyrans to be CO2 responsive.

  DOI：

  10.1021/ja1013322

文献信息

• Synthesis of Spiropyrans As Building Blocks for Molecular Switches and Dyads
  作者：Christoph Beyer、Hans-Achim Wagenknecht

  DOI：10.1021/jo100309r

  日期：2010.4.16

  The synthesis of spiropyrans was improved significantly with use of ultrasonic radiation. To show the broad applicability of this methodology a range of spiropyrans were prepared which are equipped with iodo, hydroxyl, ethinyl, or azido groups as potential building blocks for conjugation to functional π-systems or biopolymers. Representatively, the conjugation chemistry was demonstrated for the preparation

  螺吡喃的合成通过使用超声辐射而得到显着改善。为了显示该方法的广泛适用性，制备了一系列螺并吡喃并带有碘，羟基，乙炔基或叠氮基，作为与功能性π-系统或生物聚合物结合的潜在结构单元。代表性地，证明了通过“点击”型环加成反应制备具有with，per和尼罗红的螺吡喃共轭物的共轭化学。这些分子二元化合物通过光谱学表征。
• 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。
• CO₂ Triggering and Controlling Orthogonally Multiresponsive Photochromic Systems
  作者：Tamim A. Darwish、Richard A. Evans、Michael James、Nino Malic、Gerry Triani、Tracey L. Hanley

  DOI：10.1021/ja1013322

  日期：2010.8.11

  We report a new generic method of reversibly controlling the photochromism of spiropyrans. It was found that the photochromic effect of spiropyrans can be reversibly switched on and off by addition and removal of carbon dioxide (CO2) to spiropyran in alcohol solutions containing an amidine (i.e., DBU) that acts as a CO2 sensitizer. Spiropyrans are not photochromic in the presence of DBU but photochromic when CO2 is subsequently added to the solution. The CO2 is readily removed by inert gas bubbling, thus allowing facile activation and deactivation of the photochromic effect. Carbon dioxide, without the presence of the sensitizing amidine, had no effect on photochromism of the spiropyrans. Other photochromic dyes classes such as spirooxazines and chromenes are not affected by this CO2/DBU stimulus. As a result, orthogonal activation of mixtures of spirooxazines and spiropyrans was achieved to provide four color states (clear, yellow, green, and blue) by varying the combinations of the stimuli of UV, visible light, CO2, and CO2 depleted. This finding now permits the many applications using spiropyrans to be CO2 responsive.