4-butyl-2,8-dichlorobenzo[e]-1,2-oxaphosphinine 2-oxide | 917892-65-0

• 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-2,8-dichlorobenzo[e]-1,2-oxaphosphinine 2-oxide
• 英文别名: 4-butyl-2-oxo-8-chlorobenzo[e]-1,2-oxaphosporinine；4-Butyl-2,8-dichloro-2H-1,2lambda~5~-benzoxaphosphinin-2-one；4-butyl-2,8-dichloro-1,2λ5-benzoxaphosphinine 2-oxide
• CAS: 917892-65-0
• 化学式: C₁₂H₁₃Cl₂O₂P
• 分子量: 291.114
• InChiKey: YFXALHYZURZQBB-UHFFFAOYSA-N

物化性质

• 沸点：
  379.2±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-己炔 、 1,2-亚苯基三氯磷酸 以 二氯甲烷 为溶剂， 生成 4-butyl-2,8-dichlorobenzo[e]-1,2-oxaphosphinine 2-oxide 、 4-butyl-2,6-dichlorobenzo[e]-1,2-oxaphosphinine 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

文献信息

• 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.
• 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.
• Reaction of arylenedioxytrihalophosphoranes with acetylenes 12. Alkylacetylenes in the reaction with 2,2,2-trihalobenzo-1,3,2-dioxaphospholes
  作者：A. V. Nemtarev、V. F. Mironov、E. N. Varaksina、A. T. Gubaidullin、D. B. Krivolapov、R. Z. Musin、I. A. Litvinov

  DOI：10.1007/s11172-014-0409-x

  日期：2014.1

  A reaction of 2,2,2-trihalobenzo-1,3,2-dioxaphospholes with terminal alkylacetylenes proceeds under mild conditions (∼20 °C) and leads to the formation of 4-alkylbenzo[e]-1,2-oxaphosphinine 2-oxide derivatives. The presence of aliphatic substituents in acetylene decreases (as compared to their aromatic counterparts described earlier) regioselectivity of halogenation of benzo fragment in 4-alkylbenzo[e]-1,2-oxaphosphinines: besides predominant 4-alkyl-2,6-dihalobenzo[e]-1,2-oxaphosphinines, minor 2,7- and 2,8-dihalo-substituted 4-alkylbenzo[e]-1,2-oxaphosphinines are formed. An unusual thermal isomerization of 4-alkyl-2-fluorobenzo[e]-1,2-oxaphosphinines to 4-alkylidene-2-fluoro-3,4-dihydrobenzo[e]-1,2-oxaphosphinines was discovered. Molecular and supramolecular structures of some 4-alkylbenzo[e]-1,2-oxaphosphinines were studied by X-ray diffraction analysis.

  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。