1-hydroxy-4,5-benzo-2,6-dioxaphosphorinanone(3)-1-oxide | 91746-64-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1-hydroxy-4,5-benzo-2,6-dioxaphosphorinanone(3)-1-oxide
• 英文别名: salicyloyl cyclic phosphate；Salicyloyl-cycl-phosphorsaeure；2-Hydroxy-2-oxo-1,3,2lambda5-benzodioxaphosphinin-4-one；2-hydroxy-2-oxo-1,3,2λ5-benzodioxaphosphinin-4-one
• CAS: 91746-64-4
• 化学式: C₇H₅O₅P
• 分子量: 200.087
• InChiKey: NSTFEPASKPWACS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-hydroxy-4,5-benzo-2,6-dioxaphosphorinanone(3)-1-oxide 在 sodium hydroxide 作用下， 生成 磷柳酸
  参考文献：
  名称：

  环状酰基磷酸（on）酸盐抑制肠杆菌P99 C类β-内酰胺酶的机制：返还拯救

  摘要：

  如前所述 (Pratt, RF; Hammar, NJJ Am. Chem. Soc. 1998, 120, 3004.)，1-羟基-4,5-苯并-2,6-二氧杂磷啉酮(3)-1-氧化物（水杨酰基环磷酸盐）以共价方式灭活阴沟肠杆菌 P99 的 C 类β-内酰胺酶。失活的酶慢慢恢复为活性形式。本文表明，再活化涉及再生水杨酰环状磷酸酯的再循环反应，而不是共价中间体的水解。因此，失活是活性位点的缓慢可逆共价修饰。抑制剂与失活酶的热力学解离常数为 0.16 microM。用碱处理灭活的酶不会产生水杨酸，但在随后的酸水解后会产生一摩尔当量的赖氨酸丙氨酸。该结果证明水杨酰环状磷酸酯通过活性位点丝氨酸残基的（缓慢可逆的）磷酸化使酶失活。该结果与无环酰基磷酸酯的行为形成鲜明对比，后者通过酰化作用使 P99 β-内酰胺酶暂时失活（Li, N.；Pratt, RFJ Am. Chem. Soc. 1998, 120

  DOI：

  10.1021/ja011094v
• 作为产物：
  描述：

  2-氯-1,3,2-苯并二氧磷杂环己烷-4-酮 在 N-氯-N,N-二异丙胺 、 水杨酸 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以11%的产率得到1-hydroxy-4,5-benzo-2,6-dioxaphosphorinanone(3)-1-oxide
  参考文献：
  名称：

  Oxidative addition reactions of cyclic chlorophosphites and arsenites with diols and 1,2-quinones: X-ray structure of the phosphocin (ClCH2CMe2CH2O)P(O) {(O-2,4-(-bu)2C6H2)2CH2}

  摘要：

  The phosphorinane ring opens when CIP(OCH(2)CMe(2)CH(2)O) (1) is treated with diols and N-chlorodiisopropylamine (NCDA) or with quinones. X-ray structure of one such product, the phosphocin oxide, (ClCH(2)CMe(2)CH(2)O) p(O) {(O-(2,4-(t-bu)(2)C6H2)(2)CH2} (3) reveals a 'symmetrical anti' (chair) conformation of the eight membered ring. The phenylene phosphorochloridite ClP(O2C6H4) by contrast gives pentacoordinated phosphoranes in similar reactions. The arsorinane ClAs(OCH(2)CMe(2)CH(2)O) (9) on treatment with 2,2-dimethyl-l,3-propanediol-NCDA affords an arsorane formulated as ClAs(OCH(2)CMe(2)CH(2)O)(2); no reaction was apparent when 9 was treated with quinones.

  DOI：

  10.1016/s0040-4020(01)81351-x

文献信息

• Salicyloyl Cyclic Phosphate, a “Penicillin-Like” Inhibitor of β-Lactamases
  作者：R. F. Pratt、Ned J. Hammar

  DOI：10.1021/ja973313b

  日期：1998.4.1

  Salicyloyl cyclic phosphate (1-hydroxy-4,5-benzo-2,6-dioxaphosphorinanone (3)-1-oxide) was designed as a "penicillin-like" inhibitor of beta-lactamases. It was anticipated that, after nucleophilic attack on this molecule by the enzyme, the leaving group would remain tethered, and, as in the inhibition of DD-peptidases by penicillins, obstruct hydrolysis of the covalent intermediate back to free enzyme. The target molecule, hitherto only reported as a transient intermediate, was prepared by hydrolysis of the cognate cyclic phosphoryl chloride and isolated and characterized as the dicyclohexylammonium salt. It proved to transiently inhibit the class C beta-lactamase of Enterobacter cloacae P99, the class A TEM beta-lactamase, and also the DD-peptidase of Streptomyces R61. Most significantly, the half-lives of the complexes formed with these enzymes were 14, 140, and 340 min, respectively. Thus, this cyclic phosphate represents a new class of molecule leading to inert complexes of beta-lactam-recognizing enzymes.
• Said Musa A., Swamy K. C. Kumara, Mohan K. Chandra, Lakshmi N. Venkata, Tetrahedron, 50 (1994) N 23, S 6989-6998
  作者：Said Musa A., Swamy K. C. Kumara, Mohan K. Chandra, Lakshmi N. Venkata

  DOI：——

  日期：——
• US7205285B2
  申请人：——

  公开号：US7205285B2

  公开（公告）日：2007-04-17
• Mechanism of Inhibition of the Class C β-Lactamase of <i>Enterobacter </i><i>c</i><i>loacae</i> P99 by Cyclic Acyl Phosph(on)ates:  Rescue by Return
  作者：Kamaljit Kaur、Martin J. K. Lan、R. F. Pratt

  DOI：10.1021/ja011094v

  日期：2001.10.31

  As previously described (Pratt, R. F.; Hammar, N. J. J. Am. Chem. Soc. 1998, 120, 3004.), 1-hydroxy-4,5-benzo-2,6-dioxaphosphorinone(3)-1-oxide (salicyloyl cyclic phosphate) inactivates the class C beta-lactamase of Enterobacter cloacae P99 in a covalent fashion. The inactivated enzyme slowly reverts to the active form. This paper shows that reactivation involves a recyclization reaction that regenerates

  如前所述 (Pratt, RF; Hammar, NJJ Am. Chem. Soc. 1998, 120, 3004.)，1-羟基-4,5-苯并-2,6-二氧杂磷啉酮(3)-1-氧化物（水杨酰基环磷酸盐）以共价方式灭活阴沟肠杆菌 P99 的 C 类β-内酰胺酶。失活的酶慢慢恢复为活性形式。本文表明，再活化涉及再生水杨酰环状磷酸酯的再循环反应，而不是共价中间体的水解。因此，失活是活性位点的缓慢可逆共价修饰。抑制剂与失活酶的热力学解离常数为 0.16 microM。用碱处理灭活的酶不会产生水杨酸，但在随后的酸水解后会产生一摩尔当量的赖氨酸丙氨酸。该结果证明水杨酰环状磷酸酯通过活性位点丝氨酸残基的（缓慢可逆的）磷酸化使酶失活。该结果与无环酰基磷酸酯的行为形成鲜明对比，后者通过酰化作用使 P99 β-内酰胺酶暂时失活（Li, N.；Pratt, RFJ Am. Chem. Soc. 1998, 120
• Oxidative addition reactions of cyclic chlorophosphites and arsenites with diols and 1,2-quinones: X-ray structure of the phosphocin (ClCH2CMe2CH2O)P(O) {(O-2,4-(-bu)2C6H2)2CH2}
  作者：Musa A. Said、K.C.Kumara Swamy、K.Chandra Mohan、N.Venkata Lakshmi

  DOI：10.1016/s0040-4020(01)81351-x

  日期：1994.1

  The phosphorinane ring opens when CIP(OCH(2)CMe(2)CH(2)O) (1) is treated with diols and N-chlorodiisopropylamine (NCDA) or with quinones. X-ray structure of one such product, the phosphocin oxide, (ClCH(2)CMe(2)CH(2)O) p(O) (O-(2,4-(t-bu)(2)C6H2)(2)CH2} (3) reveals a 'symmetrical anti' (chair) conformation of the eight membered ring. The phenylene phosphorochloridite ClP(O2C6H4) by contrast gives pentacoordinated phosphoranes in similar reactions. The arsorinane ClAs(OCH(2)CMe(2)CH(2)O) (9) on treatment with 2,2-dimethyl-l,3-propanediol-NCDA affords an arsorane formulated as ClAs(OCH(2)CMe(2)CH(2)O)(2); no reaction was apparent when 9 was treated with quinones.