4-butyl-2,6-dichlorobenzo[e]-1,2-oxaphosphinine 2-oxide | 917892-64-9

• 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-2,6-dichlorobenzo[e]-1,2-oxaphosphinine 2-oxide
• 英文别名: 4-butyl-2-oxo-6-chlorobenzo[e]-1,2-oxaphosporinine；4-Butyl-2,6-dichloro-2H-1,2lambda~5~-benzoxaphosphinin-2-one；4-butyl-2,6-dichloro-1,2λ5-benzoxaphosphinine 2-oxide
• CAS: 917892-64-9
• 化学式: C₁₂H₁₃Cl₂O₂P
• 分子量: 291.114
• InChiKey: IBLWGHNJQYBBHT-UHFFFAOYSA-N

物化性质

• 沸点：
  379.3±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

• 作为反应物：
  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
• 作为产物：
  描述：

  、 1-己炔 生成 4-butyl-2,6-dichlorobenzo[e]-1,2-oxaphosphinine 2-oxide
  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。
• Micellar extraction of the lanthanide ions from acidic media
  作者：Yu. G. Elistratova、A. R. Mustafina、D. A. Tatarinov、V. F. Mironov、A. I. Konovalov

  DOI：10.1007/s11172-009-0309-7

  日期：2009.11

  A procedure of micellar extraction of the lanthanide ions (La, Gd, and Lu) from nitric acid media based on the use of novel phosphine oxide derivatives is developed. In the micellar extraction, complexes of the lanthanide ions with the extractant in the ratio of 1 : 2 (metal : extractant) form. The dependence of the selectivity of extraction on the length of hydrophobic radicals attached to the P=O group was shown. The conditions of the selective micellar extraction in the series La > Gd > Lu with the use of an extractant containing octyl substituents at the P=O group were found.

  开发了一种基于使用新型氧化膦衍生物从硝酸介质中胶束萃取镧系离子（La、Gd 和 Lu）的方法。在胶束萃取中，镧系元素离子与萃取剂以 1:2（金属：萃取剂）的比例形成络合物。显示了萃取选择性对连接到 P=O 基团的疏水基团长度的依赖性。找到了使用 P=O 基团上含有辛基取代基的萃取剂对 La > Gd > Lu 系列中的选择性胶束萃取的条件。
• 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。
• 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.