2-methyl-2-oxo-1,3-dioxa-2-phosphacyclohexane | 13407-03-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-methyl-2-oxo-1,3-dioxa-2-phosphacyclohexane
• 英文别名: 2-methyl-1,3,2-dioxaphosphorinane 2-oxide；2-methyl-2-oxo-1,3,2-dioxa-phosphorinane；2-methyl-2-oxo-1,3,2-dioxaphosphorinane；2-oxo-2-methyl-1,3,2-dioxaphosphorinane；O,O-1,3-trimethylene-methylphosphonate；2-methyl-[1,3,2]dioxaphosphorinane-2-oxide；2-methyl-1,3,2λ5-dioxaphosphinane 2-oxide
• CAS: 13407-03-9
• 化学式: C₄H₉O₃P
• 分子量: 136.087
• InChiKey: SKEMFEUSYWGOKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-2-oxo-1,3-dioxa-2-phosphacyclohexane 、 N-tritylcyclohexylalaninal 在 叔丁基锂 作用下， 生成 (2'R,3'S)-2-<4-cyclohexyl-2-hydroxy-3-(tritylamino)butyl>-1,3-dioxa-2-oxo-2-phosphacyclohexane
  参考文献：
  名称：

  New inhibitors of renin that contain novel phosphostatine Leu-Val replacements

  摘要：

  A novel series of renin inhibitors based on the Phe8-His9-Leu10-Val11 substructure of renin's natural substrate, angiotensinogen, is reported. These inhibitors retain the Phe8-His9 portion of the native substructure and employ novel phosphostatine Leu10-Val11 replacements (LVRs). The phosphostatine LVRs were prepared by condensing a dialkyl phosphonate ester stabilized anion with either N-t-Boc-amino aldehydes or N-tritylamino aldehydes (derived from the corresponding amino acid). Structure-activity relationships at the Leu10 side chain revealed that the LVR derived from L-cyclohexylalanine provided a 130-fold boost in potency over the LVR derived from L-leucine. The dialkyl ester moiety was varied and a loss in potency was incurred when the alkyl ester was chain extended or alpha-branched; dimethyl esters provided optimum potency. The phosphonate moiety was replaced by a half-acid half-ester phosphonate and dimethylphosphinate; both replacements lead to a loss in potency. The more potent inhibitors (IC50 = 20-50 nM) were found to be selective inhibitors for renin over porcine pepsin and bovine cathepsin D (little or no inhibition was observed at 10(-5) M).

  DOI：

  10.1021/jm00164a011
• 作为产物：
  描述：

  甲基膦酞二氯 、 1,3-丙二醇 在 三乙胺 作用下， 以 苯 为溶剂， 生成 2-methyl-2-oxo-1,3-dioxa-2-phosphacyclohexane
  参考文献：
  名称：

  Cyclische Ester und Thioester von Phosphon-, Thiophosphon- und Selenophosphons�uren

  摘要：

  DOI：

  10.1007/bf00913774

文献信息

• Studies on Organophosphorus Compounds XXVI. New Aspects on the Synthetic Study of Some Cyclic Esters of Alkylphosphonic Acids
  作者：Chengye Yuan、Shusen Li、Zhiyi Cheng

  DOI：10.1055/s-1988-27508

  日期：——

  Various methods for the synthesis of some cyclic esters of alkylphosphonic acids, namely 2-alkyl-1,3,2-dioxaphosphorinane-2-oxides and phosphepane-2-oxides were investigated. A dilution method based on the concurrent addition of alkylphosphonyl dichloride and glycol in the presence of triethylamine gave satisfactory results. Cyclic phosphonic ester with exocyclic bulky substituent on phosphorus was prepared with better yield by alcoholysis of tert-butyl phosphonyl dichloride with disodium glycolate. Phase transfer catalytic P-alkylation of cyclic phosphites proceeded smoothly in most cases. The dependence of ring size and structure of the exocyclic alkyl group on the spectroscopic behaviors of these compounds was evaluated.

  研究了一些烷基膦酸的环状酯合成方法，特别是2-烷基-1,3,2-二氧膦烷-2-氧化物和膦烷-2-氧化物。采用基于烷基膦酸二氯化物和甘油在三乙胺存在下同时添加的稀释方法，取得了令人满意的结果。通过用二钠甘油酸盐对叔丁基膦酸二氯化物进行醇解，可以更好地制备带有外环笨重取代基的环状膦酸酯，且产率更高。大多数情况下，环状膦酸酯的相转移催化P-烷基化反应顺利进行。评估了环的大小和外环烷基结构对这些化合物光谱行为的影响。
• Korschak et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1957, p. 631,634; engl. Ausg. S. 641, 643
  作者：Korschak et al.

  DOI：——

  日期：——
• Morita, Iwao; Tsuda, Masami; Kise, Masahiro, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 12, p. 4711 - 4716
  作者：Morita, Iwao、Tsuda, Masami、Kise, Masahiro、Sugiyama, Makoto

  DOI：——

  日期：——
• Arbusow et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1959, p. 1579,1583; engl. Ausg. S. 1521, 1525
  作者：Arbusow et al.

  DOI：——

  日期：——
• Organic Phosphorus Compounds. I. Reactions of Methanephosphonyl Dichloride with Glycols¹
  作者：A. F. McKay、R. O. Braun、G. R. Vavasour

  DOI：10.1021/ja01141a527

  日期：1952.11