4-butyl-6-chloro-2-hydroxy-2-oxo-benzo[e]-1,2-oxaphosphorinine | 917892-66-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-butyl-6-chloro-2-hydroxy-2-oxo-benzo[e]-1,2-oxaphosphorinine
• 英文别名: 4-butyl-6-chloro-2-hydroxybenzo[e]-1,2-oxaphosphinine 2-oxide；4-butyl-6-chloro-2-hydroxy-2-oxobenzo[e]-1,2-oxaphosporinine；4-Butyl-6-chloro-2-hydroxy-2H-1,2lambda~5~-benzoxaphosphinin-2-one；4-butyl-6-chloro-2-hydroxy-1,2λ5-benzoxaphosphinine 2-oxide
• CAS: 917892-66-1
• 化学式: C₁₂H₁₄ClO₃P
• 分子量: 272.668
• InChiKey: LDKBDQDIQMRNQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  132 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  407.4±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-butyl-6-chloro-2-hydroxy-2-oxo-benzo[e]-1,2-oxaphosphorinine 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.25h， 以88%的产率得到sodium 4-butyl-6-chlorobenzo[e]-1,2-oxaphosphinin-2-oate 2-oxide
  参考文献：
  名称：

  Reaction of arylenedioxytrihalophosphoranes with acetylenes 12. Alkylacetylenes in the reaction with 2,2,2-trihalobenzo-1,3,2-dioxaphospholes

  摘要：

  2,2,2-三卤代苯并-1,3,2-二氧磷环与末端烷基乙炔在温和条件下（20 °C～）发生反应，生成 4-烷基苯并[e]-1,2-氧膦 2-氧化物衍生物。乙炔中脂肪族取代基的存在降低了 4-烷基苯并[e]-1,2-氧杂膦中苯并片段卤化的区域选择性（与前面所述的芳香族取代基相比）：除了主要的 4-烷基-2,6-二卤代苯并[e]-1,2-氧杂膦外，还形成了少量的 2,7- 和 2,8- 二卤代 4-烷基苯并[e]-1,2-氧杂膦。发现了 4-烷基-2-氟苯并[e]-1,2-氧杂膦与 4-亚烷基-2-氟-3,4-二氢苯并[e]-1,2-氧杂膦的不寻常热异构化。通过 X 射线衍射分析研究了一些 4-烷基苯并[e]-1,2-氧杂膦的分子和超分子结构。

  DOI：

  10.1007/s11172-014-0409-x
• 作为产物：
  描述：

  4-butyl-2,6-dichlorobenzo[e]-1,2-oxaphosphinine 2-oxide 在 水 作用下， 生成 4-butyl-6-chloro-2-hydroxy-2-oxo-benzo[e]-1,2-oxaphosphorinine
  参考文献：
  名称：

  Synthesis and Chemical Properties of Benzo[e]-1,2-Oxaphosphorinine Derivatives—Analogues of Coumarins

  摘要：

  The 4-aryl(alkyl)benzo[e]-1,2-oxaphosphorine derivatives (phosphacoumarins) were obtained by the reaction of 2,2,2-trihalogenobenzo[d]-1,3,2-dioxaphospholes with terminal acetylenes. The reactions of phosphacoumarins with halogens and Grignard reagents were investigated.

  DOI：

  10.1080/10426500701764957

文献信息

• Reactions of phenylenedioxytrihalophosphoranes with arylacetylenes: XIII. Reaction of 5-tert-butyl-2,2,2-trihalo-1,3,2λ5-benzodioxaphospholes with acetylenes
  作者：V. F. Mironov、A. V. Nemtarev、E. N. Varaksina、A. A. Shtyrlina、A. T. Gubaidullin、I. A. Litvinov、A. B. Dobrynin

  DOI：10.1134/s1070428014060190

  日期：2014.6

  of natural heterocyclic compounds, coumarin and chromene. The major products (>70%) are 4-aryl-7-tert-butyl-2,6-dichloro-, 4-aryl-2-bromo-7-tert-butyl-, and 4-aryl-7-tert-butyl-2-fluoro-1,2λ5-benzoxaphosphinine 2-oxides. Hydrolysis of these compounds and their treatment with amines gives the corresponding 2-hydroxy and 2-amino derivatives, as well as ammonium salts. The structure of some compounds was

  5-反应叔丁基-2,2,2-三氯乙基，2,2,2-三溴-5-叔丁基-和2,2-二溴-5-叔丁基-2-氟-1- ，3,2λ 5 -benzodioxaphospholes与芳基-和alkylacetylenes导致2-卤代1,2λ的定量形成5 -benzoxaphosphinine 2氧化物，其可以被认为是天然的杂环化合物，香豆素和色烯的磷类似物。主要产品（> 70％）为4-芳基-7-叔丁基-2,6-二氯-，4-芳基-2-溴-7-叔丁基-和4-芳基-7-叔-丁基-2-氟- 1,2λ 5-苯并氧杂膦酸2-氧化物。这些化合物的水解及其用胺的处理产生相应的2-羟基和2-氨基衍生物以及铵盐。X射线分析证实了某些化合物的结构。
• Pyridine and benzyltriethylammonium chloride ate-complexes of 2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole in reactions with alk-1-ynes
  作者：Andrey V. Nemtarev、Vladimir F. Mironov、Elena N. Varaksina、Yulia V. Nelyubina、Mikhail Yu. Antipin、Rashid Z. Musin、Alexander I. Konovalov

  DOI：10.1016/j.mencom.2007.11.009

  日期：2007.11

  The reactions of the pyridine and benzyltriethylammonium chloride ate-complexes of 2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole with alk-1-ynes afford 4-alkyl-2,6-dichloro- and 4-alkyl-2,7-dichloro-2-oxobenzo[e]-1,2-oxaphosphorinines; preferable chlorination of the phenylene moiety at the 7-position occurs when the ate-complex of 2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole and benzyltriethylammonium chloride is used.
• The reaction of hex-1-yne with 2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole
  作者：Andrey V. Nemtarev、Elena N. Varaksina、Vladimir F. Mironov、Rashid Z. Musin、Alexander I. Konovalov

  DOI：10.1070/mc2006v016n02abeh002219

  日期：2006.1

  The title reaction gives 2,6-dichloro- and 2,8-dichloro-2-oxo-4-butylbenzo[e]-1,2-oxaphosphorinines in a ratio of 9:1.
• Reactions of 2,2-dichloro(dibromo)-2-fluorobenzo[d]-1,3,2-dioxaphospholes with alk-1-ynes
  作者：Elena N. Varaksina、Vladimir F. Mironov、Andrey V. Nemtarev、Rashid Z. Musin、Alsu A. Balandina、Shamil K. Latypov、Alexander I. Konovalov

  DOI：10.1070/mc2006v016n03abeh002321

  日期：2006.1

  The tide reactions are shown to yield mixtures of 4-alkyl-2-fluoro-2-oxobenzo[e]-1,2-oxaphosphorinine derivatives that are P-analogues of natural coumarin and alpha-chromen.
• Synthesis and Chemical Properties of Benzo[<i>e</i>]-1,2-Oxaphosphorinine Derivatives—Analogues of Coumarins
  作者：E. N. Varaksina、D. A. Tatarinov、K. Yu. Cherkin、A. V. Nemtarev、V. F. Mironov、A. I. Konovalov

  DOI：10.1080/10426500701764957

  日期：2008.1.14

  The 4-aryl(alkyl)benzo[e]-1,2-oxaphosphorine derivatives (phosphacoumarins) were obtained by the reaction of 2,2,2-trihalogenobenzo[d]-1,3,2-dioxaphospholes with terminal acetylenes. The reactions of phosphacoumarins with halogens and Grignard reagents were investigated.