10-[2-(phenyl)ethylene]-9,9-trimethyl-indolino[2,1-b]oxazolidine

• 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: 10-[2-(phenyl)ethylene]-9,9-trimethyl-indolino[2,1-b]oxazolidine
• 英文别名: 4,4-Dimethyl-3a-(2-phenylethenyl)-1,2-dihydro-[1,3]oxazolo[3,2-a]indole
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: AVXZCWUYZCROBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  10-[2-(phenyl)ethylene]-9,9-trimethyl-indolino[2,1-b]oxazolidine 、 碘甲烷 在 air 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 、 、
  参考文献：
  名称：

  通过恶唑烷的热氧化 构建高荧光的N–O七元杂环†

  摘要：

  氮杂环是有机化合物和药物的重要结构组分。在我们以前的工作中报道了一类新的具有七元杂环的恶唑烷的光氧化产物。这些光合作用的分子因其非常规的共轭结构和刚性而具有诱人的荧光材料的巨大潜力。但是，合成过程中强烈的紫外线照射会导致产生许多不良副产物，从而难以纯化和扩大所需产物的规模。在此，通过使用O 2 / CH 3 I，I 2或N的一步热氧化反应，定量合成了所需的N–O七元杂环-碘代琥珀酰亚胺（NIS）作为氧化剂。这些化合物的结构通过单晶X射线衍射确认。在热氧化过程中，所产生的柔性-CH分子电离2 CH 2 ö -基团，其攻击ÇC在氧化剂的帮助下结合，随后导致产物的形成。与具有更灵活的共轭亚结构的恶唑烷的相应开环形式相比，形成的七元杂环显示出显着增强的荧光。特别地，一些产物的荧光量子产率在红色发射区域达到0.92和0.62。理论计算表明，强荧光源于其独特的结构刚度和平面度，因此是高度共轭的电子系统

  DOI：

  10.1039/c9tc01199d
• 作为产物：
  描述：

  9,9,9a-trimethyl-2,3,9,9a-tetrahydrooxazolo[3,2-a]indole 、 苯甲醛 在 silica gel 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以76%的产率得到10-[2-(phenyl)ethylene]-9,9-trimethyl-indolino[2,1-b]oxazolidine
  参考文献：
  名称：

  Silica-Mediated Synthesis of Indolinooxazolidine-Based Molecular Switches

  摘要：

  A novel and convenient method for the synthesis of photochromic compounds is reported here. It is based on the use of commercially available untreated silica, as an efficient catalyst to perform the condensation between indolinooxazolidine derivatives and aromatic aldehydes under solvent-free conditions. The scope and limitations of this transformation were investigated and several novel photochromic indolinooxazolidines were synthesized. This methodology can also be applied to the synthesis of other photoactive compounds such as spiropyrans or spirooxazines. According to our working protocol the reaction did not require any solvent or additional reagents and gave the products within 10 min in isolated yields of up to 90%.

  DOI：

  10.1021/acs.joc.5b00282

文献信息

• LITHOGRAPHIC PRINTING PLATE PRECURSOR AND PRINTING METHOD THEREOF
  申请人：FUJIFILM Corporation

  公开号：US20150000544A1

  公开（公告）日：2015-01-01

  A lithographic printing plate precursor includes at least a white substrate and an image-recording layer, the white substrate has a reflection density of 0.25 or less at a side having the image-recording layer, and the image-recording layer contains an infrared absorbing agent, an onium salt polymerization initiator, a polymerizable compound and a color-forming compound and is capable of being removed with at least any one of printing ink and dampening water.
• LITHOGRAPHIC PRINTING PLATE PRECURSOR AND PLATE-MAKING METHOD USING SAME
  申请人：FUJIFILM Corporation

  公开号：US20190187557A1

  公开（公告）日：2019-06-20

  Provided are a thermal fusion-type lithographic printing plate precursor in which the visibility is excellent, ablation during laser exposure is suppressed, and the contamination of dampening water and printing ink during on-machine development is suppressed by a lithographic printing plate precursor having a support and an image-recording layer, in which the image-recording layer is capable of forming an image by infrared laser exposure, a non-exposed portion of the image-recording layer is removable by at least one of dampening water and printing ink on a printer, and the image-recording layer contains (1) a color developing system in which a hue change generated by infrared laser exposure is Δa/Δb≥0.6 and (2) 70% by mass or more of a thermoplastic polymer particle with respect to a solid content of the image-recording layer and a plate-making method in which the thermal fusion-type lithographic printing plate precursor is used.
• Silica-Mediated Synthesis of Indolinooxazolidine-Based Molecular Switches
  作者：György Szalóki、Lionel Sanguinet

  DOI：10.1021/acs.joc.5b00282

  日期：2015.4.17

  A novel and convenient method for the synthesis of photochromic compounds is reported here. It is based on the use of commercially available untreated silica, as an efficient catalyst to perform the condensation between indolinooxazolidine derivatives and aromatic aldehydes under solvent-free conditions. The scope and limitations of this transformation were investigated and several novel photochromic indolinooxazolidines were synthesized. This methodology can also be applied to the synthesis of other photoactive compounds such as spiropyrans or spirooxazines. According to our working protocol the reaction did not require any solvent or additional reagents and gave the products within 10 min in isolated yields of up to 90%.
• Construction of highly fluorescent N–O seven-membered heterocycles<i>via</i>thermo-oxidation of oxazolidines
  作者：Qiaonan Chen、Xiao Liang、Jiahui Du、Zhonglin Wei、Yu-Mo Zhang、Ting Zhang、Tianyou Qin、Wenbin Gao、Lan Sheng、Sean Xiao-An Zhang

  DOI：10.1039/c9tc01199d

  日期：——

  Nitrogen heterocycles are significant structural components for organic compounds and pharmaceuticals. A new class of photooxidation products of oxazolidines with seven-membered heterocycles were reported in our previous work. These photosynthesized molecules have great potential for attractive fluorescent materials due to their unusual conjugated structure and rigidity. However, the violent UV irradiation

  氮杂环是有机化合物和药物的重要结构组分。在我们以前的工作中报道了一类新的具有七元杂环的恶唑烷的光氧化产物。这些光合作用的分子因其非常规的共轭结构和刚性而具有诱人的荧光材料的巨大潜力。但是，合成过程中强烈的紫外线照射会导致产生许多不良副产物，从而难以纯化和扩大所需产物的规模。在此，通过使用O 2 / CH 3 I，I 2或N的一步热氧化反应，定量合成了所需的N–O七元杂环-碘代琥珀酰亚胺（NIS）作为氧化剂。这些化合物的结构通过单晶X射线衍射确认。在热氧化过程中，所产生的柔性-CH分子电离2 CH 2 ö -基团，其攻击ÇC在氧化剂的帮助下结合，随后导致产物的形成。与具有更灵活的共轭亚结构的恶唑烷的相应开环形式相比，形成的七元杂环显示出显着增强的荧光。特别地，一些产物的荧光量子产率在红色发射区域达到0.92和0.62。理论计算表明，强荧光源于其独特的结构刚度和平面度，因此是高度共轭的电子系统