N-(1-adamantyl)phenylphosphonochloramidate | 56252-44-9

• 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: N-(1-adamantyl)phenylphosphonochloramidate
• 英文别名: N-[chloro(phenyl)phosphoryl]adamantan-1-amine
• CAS: 56252-44-9
• 化学式: C₁₆H₂₁ClNOP
• 分子量: 309.776
• InChiKey: ARBLCPRBMQEYII-UHFFFAOYSA-N

物化性质

• 沸点：
  417.6±28.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-adamantyl)phenylphosphonochloramidate 在 盐酸 、 sodium hydroxide 作用下， 以 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 1.5h， 生成 [乙氧基(甲氧基)磷酰基]苯
  参考文献：
  名称：

  FRAGMENTATION OF A PHENYLPHOSPHONAMIDIC ACID AS A NEW TECHNIQUE FOR THE GENERATION OF PHENYL DIOXOPHOSPHORANE

  摘要：

  N-(1-Adamantyl) phenylphosphonamidic acid (3), an easily prepared solid, on heating in toluene or 1,2-dichloroethane gave the crystalline adamantylamine salt of the anhydride PhP(O)(NHAd)-O-PPh(O)(OH). The mechanism is proposed to involve first the fragmentation of 3 to form phenyl dioxophosphorane, PhPO(2), which then acts as a phosphorylating agent to unreacted 3. This mechanism was supported by the observation of first-order kinetics for the consumption of 3. When the phosphonamidic acid was fragmented in the presence of an alcohol, the intermediate PhPO(2) was trapped as the monoalkyl phenylphosphonate. The OH groups on the surface of silica gel were also phosphonylated by PhPO(2). The acidic OH group of a phosphoric acid monoester (thymyl phosphate) was phosphonylated to give Thy-O-P(O)(OH)-O-PPh(O)(OH). It is concluded from this study that N-(1-adamantyl) phenylphosphonamidic acid is a useful precursor of phenyl dioxophosphorane, which can perform valuable phosphonylation operations.

  DOI：

  10.1080/10426509608037956
• 作为产物：
  描述：

  苯膦酰二氯 、 金刚烷胺 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 7.0h， 生成 N-(1-adamantyl)phenylphosphonochloramidate
  参考文献：
  名称：

  FRAGMENTATION OF A PHENYLPHOSPHONAMIDIC ACID AS A NEW TECHNIQUE FOR THE GENERATION OF PHENYL DIOXOPHOSPHORANE

  摘要：

  N-(1-Adamantyl) phenylphosphonamidic acid (3), an easily prepared solid, on heating in toluene or 1,2-dichloroethane gave the crystalline adamantylamine salt of the anhydride PhP(O)(NHAd)-O-PPh(O)(OH). The mechanism is proposed to involve first the fragmentation of 3 to form phenyl dioxophosphorane, PhPO(2), which then acts as a phosphorylating agent to unreacted 3. This mechanism was supported by the observation of first-order kinetics for the consumption of 3. When the phosphonamidic acid was fragmented in the presence of an alcohol, the intermediate PhPO(2) was trapped as the monoalkyl phenylphosphonate. The OH groups on the surface of silica gel were also phosphonylated by PhPO(2). The acidic OH group of a phosphoric acid monoester (thymyl phosphate) was phosphonylated to give Thy-O-P(O)(OH)-O-PPh(O)(OH). It is concluded from this study that N-(1-adamantyl) phenylphosphonamidic acid is a useful precursor of phenyl dioxophosphorane, which can perform valuable phosphonylation operations.

  DOI：

  10.1080/10426509608037956

文献信息

• FRAGMENTATION OF A PHENYLPHOSPHONAMIDIC ACID AS A NEW TECHNIQUE FOR THE GENERATION OF PHENYL DIOXOPHOSPHORANE
  作者：Gyöngyi Szakal Quin、Stefan Jankowski、Louis D. Quin

  DOI：10.1080/10426509608037956

  日期：1996.8.1

  N-(1-Adamantyl) phenylphosphonamidic acid (3), an easily prepared solid, on heating in toluene or 1,2-dichloroethane gave the crystalline adamantylamine salt of the anhydride PhP(O)(NHAd)-O-PPh(O)(OH). The mechanism is proposed to involve first the fragmentation of 3 to form phenyl dioxophosphorane, PhPO(2), which then acts as a phosphorylating agent to unreacted 3. This mechanism was supported by the observation of first-order kinetics for the consumption of 3. When the phosphonamidic acid was fragmented in the presence of an alcohol, the intermediate PhPO(2) was trapped as the monoalkyl phenylphosphonate. The OH groups on the surface of silica gel were also phosphonylated by PhPO(2). The acidic OH group of a phosphoric acid monoester (thymyl phosphate) was phosphonylated to give Thy-O-P(O)(OH)-O-PPh(O)(OH). It is concluded from this study that N-(1-adamantyl) phenylphosphonamidic acid is a useful precursor of phenyl dioxophosphorane, which can perform valuable phosphonylation operations.