methyl 3-oxo-3-phenyl-2-(triphenylphosphoranylidene)propanoate | 54557-00-5

• 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: methyl 3-oxo-3-phenyl-2-(triphenylphosphoranylidene)propanoate
• 英文别名: methyl 3-phenyl-3-oxo-2-(triphenylphosphoranylidene)propionate；Triphenylphosphin-；Methyl-2-benzoyl-2-triphenylphosphoranylidenacetat；Triphenylphosphin-benzoyl-methoxycarbonyl-methylen；Triphenylphosphin-methoxycarbonyl-benzoyl-methylen；Triphenylphosphin-(benzoyl-carbomethoxy-methylen)；Methyl 3-oxo-3-phenyl-2-(triphenyl-lambda5-phosphanylidene)propanoate；methyl 3-oxo-3-phenyl-2-(triphenyl-λ5-phosphanylidene)propanoate
• CAS: 54557-00-5
• 化学式: C₂₈H₂₃O₃P
• 分子量: 438.463
• InChiKey: ICZFNVKHIGLUKA-UHFFFAOYSA-N

物化性质

• 熔点：
  133-135 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  588.6±33.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-oxo-3-phenyl-2-(triphenylphosphoranylidene)propanoate 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 以100%的产率得到methyl 2,3-dioxo-3-phenylpropanoate
  参考文献：
  名称：

  Selective Oxidation of Phosphorus Ylides by Dimethyldioxirane. Application to the Formation of Vicinal Tricarbonyls

  摘要：

  Dimethyldioxirane (DMD) has proven to be an effective reagent for the selective conversion of phosphoranylidene intermediates 4 to the corresponding vicinal tricarbonyls 5. Unlike existing oxidation protocols which employ relatively vigorous conditions, this transformation is conducted rapidly at low temperature under neutral conditions, without the necessity of an aqueous workup. Selective oxidation of the phosphorus ylides in the presence of a variety of sensitive functionality was achieved by lowering the reaction temperature and controlling the concentration of oxidant.

  DOI：

  10.1021/jo00130a023
• 作为产物：
  描述：

  甲氧羰基亚甲基三苯基正膦 生成 methyl 3-oxo-3-phenyl-2-(triphenylphosphoranylidene)propanoate
  参考文献：
  名称：

  DOLESCHALL G., SYNTHESIS (BRD), 1981, NO 6, 478-480

  摘要：

  DOI：

文献信息

• Palladium-Catalyzed Ylidyl-Carbonylation of Aryl Halides To Produce α-Acylphosphoranes
  作者：Xiaojun Guo、Wei Ma、Dong Xue、Chao Wang、Jianliang Xiao

  DOI：10.1021/acs.orglett.6b02278

  日期：2016.10.7

  An efficient synthesis of α-acylphosphoranes by palladium-catalyzed carbonylation of aryl iodides with carbon monoxide and stabilized phosphonium ylides has been developed. Featuring 44 examples, the protocol displayed a wide substrate scope under mild reaction conditions, showcasing its potential in synthetic organic chemistry.

  已经开发了通过钯催化一氧化碳和稳定化的碘化ides的钯催化的芳基碘的羰基化反应，可以高效合成α-酰基phosph。该方案包含44个实例，在温和的反应条件下显示了广泛的底物范围，显示了其在合成有机化学中的潜力。
• DNA-PK INHIBITORS
  申请人：Martin Morrison Barr Niall

  公开号：US20070238729A1

  公开（公告）日：2007-10-11

  The invention relates to the use of compounds of formula (I) and isomers, salts, solvates, chemically protected forms, and prodrugs thereof, in the preparation of a medicament for inhibiting the activity of DNA-PK, wherein R 1 and R 2 are independently hydrogen, an optionally substituted C 1-7 alkyl group, C 3-20 heterocyclyl group, or C 5-20 aryl group, or may together form, along with the nitrogen atom to which they are attached, an optionally substituted heterocyclic ring having from 4 to 8 ring atoms; X and Y are selected from CR 4 and O, O and CR′ 4 and NR″ 4 and N, where the unsaturation is in the appropriate place in the ring, and where one of R 3 and R 4 or R′ 4 is an optionally substituted C 3-20 heteroaryl or C 5-20 aryl group, and the other of R 3 and R 4 or R′ 4 is H, or R 3 and R 4 or R″ 4 together are -A-B—, which collectively represent a fused optionally substituted aromatic ring. The compounds also selectively inhibit the activity of DNA-PK compared to PI 3-kinase and/or ATM.

  本发明涉及使用式(I)的化合物及其异构体、盐、溶剂合物、化学保护形式和前药，在制备抑制DNA-PK活性的药物方面有用。其中，R1和R2独立地表示氢、可选取代的C1-7烷基、C3-20杂环基或C5-20芳基，或者与它们连接的氮原子一起形成可选取代的含有4到8个环原子的杂环环；X和Y选自CR4和O，O和CR'4以及NR"4和N，其中不饱和度在环中适当位置，其中R3和R4或R'4中的一个为可选取代的C3-20杂芳基或C5-20芳基，而另一个为H，或者R3和R4或R"4在一起为-A-B-，代表一种融合的可选取代芳香环。这些化合物与PI 3-激酶和/或ATM相比，具有选择性地抑制DNA-PK的活性。
• Maerkl,G., Chemische Berichte, 1961, vol. 94, p. 3005 - 3010
  作者：Maerkl,G.

  DOI：——

  日期：——
• Bestman,H.J.; Geismann,C., Justus Liebigs Annalen der Chemie, 1977, p. 282 - 287
  作者：Bestman,H.J.、Geismann,C.

  DOI：——

  日期：——
• Pyranone, Thiopyranone, and Pyridone Inhibitors of Phosphatidylinositol 3-Kinase Related Kinases. Structure−Activity Relationships for DNA-Dependent Protein Kinase Inhibition, and Identification of the First Potent and Selective Inhibitor of the Ataxia Telangiectasia Mutated Kinase
  作者：Jonathan J. Hollick、Laurent J. M. Rigoreau、Celine Cano-Soumillac、Xiaoling Cockcroft、Nicola J. Curtin、Mark Frigerio、Bernard T. Golding、Sophie Guiard、Ian R. Hardcastle、Ian Hickson、Marc G. Hummersone、Keith A. Menear、Niall M. B. Martin、Ian Matthews、David R. Newell、Rachel Ord、Caroline J. Richardson、Graeme C. M. Smith、Roger J. Griffin

  DOI：10.1021/jm061121y

  日期：2007.4.1

  Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholino-pyran-4-ones and 2-morpholino-thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6-(morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.