4-Chloro-3-methyl-1-(2,4,6-trimethylphenyl)-1,2-dihydrophosphinine 1-oxide | 352463-80-0

• 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: 4-Chloro-3-methyl-1-(2,4,6-trimethylphenyl)-1,2-dihydrophosphinine 1-oxide
• 英文别名: 4-chloro-3-methyl-1-(2,4,6-trimethylphenyl)-2H-1lambda5-phosphinine 1-oxide；4-chloro-3-methyl-1-(2,4,6-trimethylphenyl)-2H-1λ5-phosphinine 1-oxide
• CAS: 352463-80-0
• 化学式: C₁₅H₁₈ClOP
• 分子量: 280.734
• InChiKey: LNQUGKHWAUVAGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  四氰基乙烯 、 4-Chloro-3-methyl-1-(2,4,6-trimethylphenyl)-1,2-dihydrophosphinine 1-oxide 、 4-Chloro-5-methyl-1-(2,4,6-trimethylphenyl)-1,2-dihydrophosphinine 1-oxide 以 四氢呋喃 为溶剂， 反应 96.0h， 生成 2-[4-Chloro-5-methyl-1-oxo-1-(2,4,6-trimethyl-phenyl)-1H-1λ⁵-phosphinin-2-ylidene]-malononitrile 、 2-[4-Chloro-3-methyl-1-oxo-1-(2,4,6-trimethyl-phenyl)-1H-1λ⁵-phosphinin-2-ylidene]-malononitrile
  参考文献：
  名称：

  Efficient Synthesis of 2,8‐Diphosphatricyclo[5.3.1.1^2,6]dodeca‐3,5,9‐triene 2,8‐Dioxides

  摘要：

  The reaction of 1,2-dihydrophosphnine oxides (3a-3d) with tetracyanoethylene (TCNE) did not follow the Diels-Alder protocol, rather the corresponding diphosphatricyclododecatrienes (4a-4d) were formed in good yields. Interaction of the mesityl-dihydrophosphinine oxide (3f) with TCNE resulted in the formation of an alpha-dicyanomethylene derivative (5).

  DOI：

  10.1081/scc-120028634
• 作为产物：
  描述：

  3-Methyl-1-(2,4,6-trimethylphenyl)-2,5-dihydro-1H-phosphole oxide 在 sodium hydroxide 、 苄基三乙基氯化铵 作用下， 反应 5.0h， 生成 4-Chloro-3-methyl-1-(2,4,6-trimethylphenyl)-1,2-dihydrophosphinine 1-oxide
  参考文献：
  名称：

  The reaction of 1-(2,4,6-trimethylphenyl)-1,2-dihydrophosphinine 1-oxides with dimethyl acetylenedicarboxylate; a [4+2] or a [2+2] cycloaddition?

  摘要：

  The reaction of dimethyl acetylenedicarboxylate (DMAD) with 3- and 5-methyl-1-aryl-1,2-dihydrophosphinine oxides (6a and 6b, respectively) obtained by the two-step ring enlargement of 2,5-dihydro-1H-phosphole oxide 4 followed different routes. Isomer 6a entered into a [4+2] cycloaddition with DMAD giving, although in low yield, phosphabicyclooctadiene 7, while 6b reacted with the acetylene moiety according to a recently discovered [2+2] protocol to afford spirocyclic oxaphosphete 8. The reaction of isomers 6a and 6b with N-phenylmaleimide under forcing conditions furnished the expected Diels–Alder cycloadducts (10a and 10b, respectively). Hence, depending on the reactant, isomer 6b displayed a dual reactivity.

  DOI：

  10.1039/b010080n