[3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2λ⁵-benzo[e][1,3,2]oxazaphosphinin-2-yl]phenylmethanol | 950694-20-9

• 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: [3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2λ⁵-benzo[e][1,3,2]oxazaphosphinin-2-yl]phenylmethanol
• 英文别名: [3-(3-chloro-4-fluorophenyl)-2-oxido-4H-1,3,2-benzoxazaphosphinin-2-ium-2-yl]-phenylmethanol
• CAS: 950694-20-9
• 化学式: C₂₀H₁₆ClFNO₃P
• 分子量: 403.777
• InChiKey: GBICCUODYOGUFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2λ⁵-benzo[e][1,3,2]oxazaphosphinin-2-yl]phenylmethanol 、 2-chloro-3-(3-chloro-4-fluorophenyl)-3,4-dihydro-2H-benzo[e][1,3,2]oxazaphosphinine 在 三乙胺 作用下， 以 苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis and anticancer activity of new class of bisphosphonates/phosphanamidates

  摘要：

  Novel bis-heterocyclic bisphosphonates/phosphonamidates were synthesized utilizing the Pudovick reaction. The employment Of Nb2O5 as catalyst was found to increase the yields and purity of the bisbenzoxazaphosphine derivatives (13a-h). Their anticancer activity studies in vitro, on three human tumor cell lines NCI-H460 (lung large cell), MCF-7 (breast adenocarcinoma), and SF-268 (central nervous system glioblastoma), showed that bis-[3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2 lambda(5)-benzo[e][1,3,2]oxazaphosphinin-2-yl]arylmethanes (13a-h) and [(4-chlorophenyl)-(hydroxyamidophosphinoyl)-methyl]phosphonic acid (14) exhibited significant anticancer activity. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.05.014
• 作为产物：
  描述：

  3-(3-chloro-4-fluorophenyl)-3,4-dihydrobenzo[e][1,3,2]oxazaphosphinine 2-oxide 、 苯甲醛 在 niobium(V) oxide 三乙胺 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 [3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2λ⁵-benzo[e][1,3,2]oxazaphosphinin-2-yl]phenylmethanol
  参考文献：
  名称：

  Synthesis and anticancer activity of new class of bisphosphonates/phosphanamidates

  摘要：

  Novel bis-heterocyclic bisphosphonates/phosphonamidates were synthesized utilizing the Pudovick reaction. The employment Of Nb2O5 as catalyst was found to increase the yields and purity of the bisbenzoxazaphosphine derivatives (13a-h). Their anticancer activity studies in vitro, on three human tumor cell lines NCI-H460 (lung large cell), MCF-7 (breast adenocarcinoma), and SF-268 (central nervous system glioblastoma), showed that bis-[3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2 lambda(5)-benzo[e][1,3,2]oxazaphosphinin-2-yl]arylmethanes (13a-h) and [(4-chlorophenyl)-(hydroxyamidophosphinoyl)-methyl]phosphonic acid (14) exhibited significant anticancer activity. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.05.014

文献信息

• Synthesis of [3-(3-Chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2<i>H</i>-2λ⁵- benzo[<i>e</i>][1,3,2]oxazaphosphinin-2-yl]-(aryl/alkyl) Methanols and Their Bioactivity on Sugarcane Smut
  作者：Y. B. Kiran、P. Vasu Govardhana Reddy、C. Devendranath Reddy、D. Gunasekar、N. P. Eswara Reddy

  DOI：10.1021/jf070850z

  日期：2007.8.1

  Synthesis of some new substituted [3-(3-chloro-4-fluorophenyl)-2-oxo-3,4-dihydro-2H-2 lambda(5)-benzo[e][1,3,2]oxazaphosphinin-2-yl]-(aryl/alkyl)methanols (7a-k) based on the Pudovick reaction was accomplished in the presence of niobium pentoxide (Nb2O5) without using an external chiral ligand. Nb2O5 appears to form the metal complex intermediate catalyst system (6) by reacting with 3-(3-chloro-4-fluoro-phenyl)-3,4-dihydrobenzo[e][1,3,2]oxazaphosphinine-2-oxide (4), which not only directs the Pudovick addition reactions of aldehyde but also increases the yields and purity of the products. These compounds exhibited a lethal effect on whip smut of sugarcane and were degraded in the environment in the presence of bacteria and fungi to nontoxic phosphate residues that act as possible plant nutrients. Thus, a new class of benzooxazaphosphininyl methanol derivatives that act in synergy both as antipathogens and as plant nutrients in the environment have been discovered.