2,3-dimethylphenyl 2-(triphenylphosphaneylidene)acetate | 190189-07-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-dimethylphenyl 2-(triphenylphosphaneylidene)acetate
• 英文别名: (Triphenyl-λ⁵-phosphanylidene)-acetic acid 2,3-dimethyl-phenyl ester；(2,3-dimethylphenyl) 2-(triphenyl-λ5-phosphanylidene)acetate
• CAS: 190189-07-2
• 化学式: C₂₈H₂₅O₂P
• 分子量: 424.479
• InChiKey: HVRHADYQNQEMEM-UHFFFAOYSA-N

物化性质

• 沸点：
  581.2±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,3-dimethylphenyl 2-(triphenylphosphaneylidene)acetate 以 二氯甲烷 、 xylene 为溶剂， 反应 18.0h， 生成 4-Benzhydrylidene-3-[1-(2,3-dimethyl-phenoxycarbonyl)-meth-(E)-ylidene]-2,2-diphenyl-cyclobutanecarboxylic acid 2,3-dimethyl-phenyl ester
  参考文献：
  名称：

  Cycloadditionen. 26. Einfluß von Substituenten in der allenischen ω-Position auf das Thermische Verhalten von Allencarbonsäurearylester

  摘要：

  The [(aryloxycarbonyl)methyl]triphenylphosphonium salts (1a and i), obtained by reaction of aryl bromoacetates with triphenylphophine, react with the acid chlorides 3 in the presence of two equivalents of triethylamine to give the phenyl- or the (1-naphthyl)-2,3-alkadienoates (4a-d and 4e-h), respectively, in the most cases accompanied by the aryl alkynoates 6 and 7 and/or with the naphthyl esters 8 of the used acids. Treatment of the [(aryloxycarbonyl)methyl] triphenylphosphonium salts (1a-i) with triethylamine furnishes the phosphoranes 2a-i, which are transformed by reaction with diphenylketene into the aryl 3,3-diphenyl-2,3-butadienoates (5). Heating of the derivatives 4a-d and 5a, bearing the unsubstituted phenyl nucleus in the ester moiety, leads to destruction, while heating of the naphthyl esters 4e-h and 5i - room temperature is sufficient in some cases - induces the IMDA-reaction to give the benzo-tricycles 9a-e. Heating of the 4,4-diphenyl-2,3-butadienoates (5b-h), bearing the alkylsubstituted phenyl ring within the ester component, induces radical dimerization to give the cylobutanes 10b-h, which represent the head to tail dimers.

  DOI：

  10.1002/prac.19973390142
• 作为产物：
  描述：

  [2-(2,3-Dimethylphenoxy)-2-oxoethyl](triphenyl)phosphanium bromide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以96%的产率得到2,3-dimethylphenyl 2-(triphenylphosphaneylidene)acetate
  参考文献：
  名称：

  Cycloadditionen. 26. Einfluß von Substituenten in der allenischen ω-Position auf das Thermische Verhalten von Allencarbonsäurearylester

  摘要：

  The [(aryloxycarbonyl)methyl]triphenylphosphonium salts (1a and i), obtained by reaction of aryl bromoacetates with triphenylphophine, react with the acid chlorides 3 in the presence of two equivalents of triethylamine to give the phenyl- or the (1-naphthyl)-2,3-alkadienoates (4a-d and 4e-h), respectively, in the most cases accompanied by the aryl alkynoates 6 and 7 and/or with the naphthyl esters 8 of the used acids. Treatment of the [(aryloxycarbonyl)methyl] triphenylphosphonium salts (1a-i) with triethylamine furnishes the phosphoranes 2a-i, which are transformed by reaction with diphenylketene into the aryl 3,3-diphenyl-2,3-butadienoates (5). Heating of the derivatives 4a-d and 5a, bearing the unsubstituted phenyl nucleus in the ester moiety, leads to destruction, while heating of the naphthyl esters 4e-h and 5i - room temperature is sufficient in some cases - induces the IMDA-reaction to give the benzo-tricycles 9a-e. Heating of the 4,4-diphenyl-2,3-butadienoates (5b-h), bearing the alkylsubstituted phenyl ring within the ester component, induces radical dimerization to give the cylobutanes 10b-h, which represent the head to tail dimers.

  DOI：

  10.1002/prac.19973390142

文献信息

• A Molecular Engineering Approach to Achieve Wavelength-Selective Photorelease Using a Dynamic Photocage
  作者：Souvik Ray、Saikat Roy、Suchhanda Biswas、Mamata Ojha、N. D. Pradeep Singh

  DOI：10.1021/acs.orglett.4c02194

  日期：2024.7.26

  We introduce a molecular engineering strategy for wavelength-selective photorelease of alcohols and carboxylic acids, employing a dynamic photocage featuring an (E)-3-(6-acetyl-2-hydroxynaphthalen-1-yl)acrylate moiety. Initially activated by visible light (λ ≥ 410 nm), it releases alcohol, generating a second photocage. Subsequent exposure to shorter wavelengths (λ ≤ 365 nm) selectively releases carboxylic

  我们引入了一种用于醇和羧酸的波长选择性光释放的分子工程策略，采用具有( E )-3-(6-乙酰基-2-羟基萘-1-基)丙烯酸酯部分的动态光笼。它最初被可见光 (λ ≥ 410 nm) 激活，释放酒精，产生第二个光笼。随后暴露于较短波长（λ ≤ 365 nm）会选择性地释放羧酸，但速率会降低。