diethyl (2,4,6-trimethylbenzoyl)phosphonate | 76814-91-0

• 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: diethyl (2,4,6-trimethylbenzoyl)phosphonate
• 英文别名: Diethyl 2,4,6-trimethylbenzoylphosphonate；diethoxyphosphoryl-(2,4,6-trimethylphenyl)methanone
• CAS: 76814-91-0
• 化学式: C₁₄H₂₁O₄P
• 分子量: 284.292
• InChiKey: KDONFNVMZBKJTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  108-109 °C(Press: 0.07 Torr)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (2,4,6-trimethylbenzoyl)phosphonate 在 三(2-氯乙基)胺 、 硫酸 作用下， 以 氯仿 为溶剂， 反应 20.0h， 以43%的产率得到2,4,6-三甲基苯胺
  参考文献：
  名称：

  二烷基酰基膦酸酯的施密特反应

  摘要：

  酮的施密特重排的范围已扩展到酰基膦酸二烷基酯 (11a-111)。令人惊讶的是，发现 11a-11d 和 11g，其中酰基部分是单独的苯甲酰基或带有吸电子或轻度放电子取代基的苯甲酰基，产生了绝大多数由芳基的 C 到 N 迁移产生的产物组（N-芳基氨基甲酰基膦酸酯，12 和 N-芳基甲酰胺，15）。相反，带有强大的电子释放对烷氧基的芳烃羰基膦酸酯产生由膦酸酯基团从 C 迁移到 N 或消除的产物（N-芳烃羰基磷酰胺二烷基酯，13 和芳烃甲腈，分别为 17）

  DOI：

  10.1021/ja00082a024
• 作为产物：
  描述：

  diethyl α-hydroxy-2,4,6-trimethylbenzylphosphonate 在 zinc dichromate(VI) 作用下， 以90%的产率得到diethyl (2,4,6-trimethylbenzoyl)phosphonate
  参考文献：
  名称：

  通过在无溶剂条件下用重铬酸锌三水合物（ZnCr 2 O 7 ·3H 2 O）氧化α-羟基膦酸酯来高产率地制备α-酮膦酸酯

  摘要：

  通过三水合重铬酸锌在无溶剂条件下以高收率和高产率将各种类型的α-羟基膦酸酯转化为α-酮膦酸酯。

  DOI：

  10.1016/s0040-4039(01)00712-2

文献信息

• Chlorosilane-Catalyzed Coupling of Hydrogen Phosphine Oxides with Acyl Chlorides Generating Acylphosphine Oxides
  作者：Jian-Qiu Zhang、Li-Biao Han

  DOI：10.1021/acs.orglett.0c01384

  日期：2020.6.19

  report a new method for the synthesis of acylphosphine oxides by the direct coupling of hydrogen phosphine oxides and acyl chlorides mediated by chlorosilanes. This new protocol is greener and safer, because it precludes the generation of volatile haloalkanes and the use of oxidants employed in the conventional methods. Moreover, moisture-unstable acylphosphine oxides that are difficult to prepare via the

  我们报告了一种新的合成方法，该方法通过氢膦氧化物和氯硅烷介导的酰氯的直接偶联来合成酰基膦氧化物。该新方案更环保，更安全，因为它避免了挥发性卤代烷烃的产生和常规方法中所用氧化剂的使用。而且，使用这种新方法可以产生难以通过常规方法制备的水分不稳定的酰基膦氧化物。
• Preparation of α-ketophosphonates by oxidation of α-hydroxyphosphonates with neutral alumina supported potassium permanganate (NASPP) under solvent-free conditions and potassium permanganate in dry benzene
  作者：Habib Firouzabadi、Nasser Iranpoor、Sara Sobhani

  DOI：10.1016/s0040-4039(01)02146-3

  日期：2002.1

  Various types of α-hydroxyphosphonates were converted to α-ketophosphonates in high yields by potassium permanganate in dry benzene or by neutral alumina supported potassium permanganate (NASPP) under solvent-free conditions.

  在无溶剂条件下，通过在干苯中的高锰酸钾或中性氧化铝负载的高锰酸钾（NASPP），可以将各种类型的α-羟基膦酸酯高产率地转化为α-酮膦酸酯。
• Photocurable compositions with acylphosphine oxide photoinitiator
  申请人：BASF Aktiengesellschaft

  公开号：US04710523A1

  公开（公告）日：1987-12-01

  Acylphosphine oxide compounds of the general formula ##STR1## where R.sup.1 is alkyl, cyclohexyl, cyclopentyl, aryl which is unsubstituted or substituted by halogen, alkyl or alkoxy, or an S-containing or N-containing five-membered or six-membered heterocyclic radical, R.sup.2 has one of the meanings of R.sup.1 (but R.sup.1 and R.sup.2 may be identical or different) or is alkoxy, aryloxy or aralkoxy, or R.sup.1 and R.sup.2 together form a ring and R.sup.3 is an at least disubstituted phenyl, pyridyl, furyl or thienyl radical which carries, at least at the two carbon atoms adjacent to the linkage point of the carbonyl group, the substituents A and B, which may be identical or different, and each of which is alkyl, alkoxy or alkylthio of 1 to 6 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, phenyl or halogen, or R.sup.3 is .alpha.-naphthyl substituted by A and B at least in the 2- and 8-positions or is .beta.-naphthyl substituted by A and B at least in the 1- and 3-positions, a process for the preparation of these acylphosphine oxide compounds from acid halides of the general formula ##STR2## where X is chlorine or bromine, and a phosphine of the general formula ##STR3## and the use of these acylphosphine oxide compounds as photoinitiators in photopolymerizable surface coatings, finishes and printing inks.

  一般式为##STR1##的酰基膦氧化物化合物，其中R.sup.1是烷基、环己基、环戊基、芳基，该芳基未取代或通过卤素、烷基或烷氧基进行取代，或者是含有S或N的五元或六元杂环基团，R.sup.2具有R.sup.1的一种含义（但R.sup.1和R.sup.2可以相同或不同），或者是烷氧基、芳氧基或芳基烷氧基，或者R.sup.1和R.sup.2一起形成一个环，并且R.sup.3是至少二取代的苯基、吡啶基、呋喃基或噻吩基基团，其携带在羰基团连接点相邻的至少两个碳原子处的取代基A和B，这些取代基可以相同也可以不同，每个取代基是1到6个碳原子的烷基、烷氧基或烷硫基，5到7个碳原子的环烷基、苯基或卤素，或者R.sup.3是在2-和8-位置至少取代A和B的α-萘基，或在1-和3-位置至少取代A和B的β-萘基。本发明还提供了从一般式为##STR2##的酸卤制备这些酰基膦氧化物化合物的方法，其中X是氯或溴，以及在光聚合表面涂层、饰面和印刷油墨中使用这些酰基膦氧化物化合物作为光引发剂。
• Acylphosphine oxide compounds their preparation and use
  申请人：BASF Aktiengesellschaft

  公开号：US04298738A1

  公开（公告）日：1981-11-03

  Acylphosphine oxide compounds of the general formula ##STR1## where R.sup.1 is alkyl, cyclohexyl, cyclopentyl, aryl which is unsubstituted or substituted by halogen, alkyl or alkoxy, or an S-containing or N-containing five-membered or six-membered heterocyclic radical, R.sup.2 has one of the meanings of R.sup.1 (but R.sup.1 and R.sup.2 may be identical or different) or is alkoxy, aryloxy or aralkoxy, or R.sup.1 and R.sup.2 together form a ring and R.sup.3 is an at least disubstituted phenyl, pyridyl, furyl or thienyl radical which carries, at least at the two carbon atoms adjacent to the linkage point of the carbonyl group, the substituents A and B, which may be identical or different, and each of which is alkyl, alkoxy or alkythio of 1 to 6 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, phenyl or halogen, or R.sup.3 is .alpha.-naphthyl substituted by A and B at least in the 2- and 8-positions or is .beta.-naphthyl substituted by A and B at least in the 1- and 3-positions, a process for the preparation of these acylphosphine oxide compounds from acid halides of the general formula ##STR2## where X is chlorine or bromine, and a phosphine of the general formula ##STR3## and the use of these acylphosphine oxide compounds as photoinitiators in photopolymerizable surface coatings, finishes and printing inks.

  一般式为##STR1##的酰基膦氧化物化合物，其中R.sup.1是烷基，环己基，环戊基，未取代或取代为卤素，烷基或烷氧基的芳基，或者是含有S或N的五元或六元杂环基团，R.sup.2具有R.sup.1的一种含义（但R.sup.1和R.sup.2可以相同或不同），或者是烷氧基，芳氧基或芳基烷氧基，或者R.sup.1和R.sup.2一起形成环，R.sup.3是至少二取代的苯基，吡啶基，呋喃基或噻吩基基团，其携带在羰基团连接点相邻的至少两个碳原子上的取代基A和B，这些取代基A和B可以相同或不同，且每个取代基都是1至6个碳原子的烷基，烷氧基或烷硫基，5至7个碳原子的环烷基，苯基或卤素，或者R.sup.3是α-萘基，在2-和8-位置上至少被A和B取代，或者是β-萘基，在1-和3-位置上至少被A和B取代，一种从一般式##STR2##的酸卤化物（其中X是氯或溴）和一般式##STR3##的膦化合物制备这些酰基膦氧化物化合物的方法，以及将这些酰基膦氧化物化合物用作光引发剂，用于光聚合表面涂层，饰面和印刷油墨。
• PHOTOPOLYMERIZATION INITIATOR COMPOSITION FOR VISIBLE RAY POLYMERIZABLE ADHESIVE
  申请人：ADELL CO., LTD.

  公开号：EP0627476A1

  公开（公告）日：1994-12-07

  A photopolymerization initiator for a visible ray polymerizable adhesive, and a visible ray polymerizable adhesive comprising the initiator, an aliphatic tertiary amine and a radical-polymerizable monomer. The adhesive has a good adhesiveness, a good transparency free from discoloration after photopolymerization, and such an excellent light resistance that it is minimized in the discoloration and deterioration in the ultraviolet radiation test. The adhesive is also excellent in the photopolymerizability by not only visible rays but also near-ultraviolet rays and is minimized in the problem of the transparency being impaired by coloration or discoloration when irradiated with either of the rays.

  一种用于可见光可聚合粘合剂的光聚合引发剂，以及一种由该引发剂、脂肪族叔胺和可自由基聚合单体组成的可见光可聚合粘合剂。该粘合剂具有良好的粘合性，在光聚合后具有良好的透明度，不会变色，而且耐光性极佳，在紫外线辐射测试中变色和变质的情况极少。此外，该粘合剂不仅在可见光下，而且在近紫外线下的光聚合性也很好，在用可见光或近紫外线照射时，透明度因着色或变色而受损的问题也很小。