2-methoxy-3,6-dihydro-1,2-oxaphosphinine 2-oxide | 53910-02-4

• 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-methoxy-3,6-dihydro-1,2-oxaphosphinine 2-oxide
• 英文别名: methyl 2-butenylphosphonate；Methyl 2-Butenylphosphonat；2-methoxy-3,6-dihydro-2H-[1,2]oxaphosphinine 2-oxide；2-Methoxy-3,6-dihydro-1,2lambda5-oxaphosphinine 2-oxide；2-methoxy-3,6-dihydro-1,2λ5-oxaphosphinine 2-oxide
• CAS: 53910-02-4
• 化学式: C₅H₉O₃P
• 分子量: 148.098
• InChiKey: BYQBQRILGVYVEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-methoxy-3,6-dihydro-1,2-oxaphosphinine 2-oxide 在 四氧化锇 、 氧化-4-甲基吗啉一水合物 、 柠檬酸 作用下， 以 异丙醇 、 丙酮 、 叔丁醇 为溶剂， 反应 48.0h， 以78%的产率得到2-methoxy-3,6-dihydro-1,2-oxaphosphorinane-4,5-diol 2-oxide
  参考文献：
  名称：

  Synthesis of Cyclic Phosphonate Analogues of (Lyso)phosphatidic Acid Using a Ring-Closing Metathesis Reaction

  摘要：

  We describe a versatile and efficient method for the preparation of acyloxy-substituted six-membered cyclic phosphonates using the ring-closing metathesis. After closure, the key cyclic phosphonate intermediate was dihydroxylated and converted to a new class of conformationally constrained PA and LPA analogues. The oleoyloxy-substituted cyclic phosphonate 4 had unique receptor-selective properties as a ligand, showing partial activation of the LPA(2) GPCR and weak antagonism of the LPA(1) GPCR.

  DOI：

  10.1021/jo0607919
• 作为产物：
  描述：

  (4-bromo-but-2-enyl)-phosphonic acid dimethyl ester 生成 2-methoxy-3,6-dihydro-1,2-oxaphosphinine 2-oxide
  参考文献：
  名称：

  Monomeric methyl metaphosphate

  摘要：

  DOI：

  10.1021/ja00828a028

文献信息

• Spectroscopic identification of monomeric methyl metaphosphate
  作者：Xiaofang Zhao、Chao Song、Kemiao Hong、Xinfang Xu、Changyun Chen、Xianxu Chu、Xiaoqing Zeng

  DOI：10.1039/c9dt03367j

  日期：——

  Monomeric methyl metaphosphate (CH3OPO2), a highly electrophilic phosphorylating intermediate in chemical oligonucleotide synthesis, has been generated in the gas phase by high-vacuum flash pyrolysis (1000 K) of methyl 2-butenylphosphonate. In addition to the unambiguous characterization using IR spectroscopy in solid N2-, Ar-, and Ne-matrices, the formation CH3OPO2 in the photooxidation of the prototypical

  单体偏磷酸甲酯（CH 3 OPO 2）是化学寡核苷酸合成中的高度亲电性磷酸化中间体，已通过气相的2-丁烯基膦酸甲酯快速真空热解（1000 K）生成。除了在固体N 2-，Ar-和Ne矩阵中使用IR光谱法进行明确表征外，在O 2与18 O同位素加扰下，典型的次膦氧化物CH 3 PO被O 2光氧化时，形成CH 3 OPO 2。在固体N 2-基体（15 K）中观察到“ α”。
• Monomeric methyl metaphosphate. II. Electrophilic aromatic substitution
  作者：Charles H. Clapp、Arnold Satterthwait、F. H. Westheimer

  DOI：10.1021/ja00856a052

  日期：1975.11
• Synthesis of Cyclic Phosphonate Analogues of (Lyso)phosphatidic Acid Using a Ring-Closing Metathesis Reaction
  作者：Honglu Zhang、Ryoko Tsukuhara、Gabor Tigyi、Glenn D. Prestwich

  DOI：10.1021/jo0607919

  日期：2006.8.1

  We describe a versatile and efficient method for the preparation of acyloxy-substituted six-membered cyclic phosphonates using the ring-closing metathesis. After closure, the key cyclic phosphonate intermediate was dihydroxylated and converted to a new class of conformationally constrained PA and LPA analogues. The oleoyloxy-substituted cyclic phosphonate 4 had unique receptor-selective properties as a ligand, showing partial activation of the LPA(2) GPCR and weak antagonism of the LPA(1) GPCR.
• Monomeric methyl metaphosphate
  作者：Charles H. Clapp、F. H. Westheimer

  DOI：10.1021/ja00828a028

  日期：1974.10