4-methyl-1-phenyl-2-phospholene 1-oxide | 54546-51-9

• 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: 4-methyl-1-phenyl-2-phospholene 1-oxide
• 英文别名: 2,3-Dihydro-3-methyl-1-phenyl-1H-phosphole 1-oxide；3-methyl-1-phenyl-2,3-dihydro-1λ5-phosphole 1-oxide
• CAS: 54546-51-9
• 化学式: C₁₁H₁₃OP
• 分子量: 192.197
• InChiKey: HAXGJIFBSLNBTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  苯基磷杂环戊-3-烯 、 碘甲烷 在 2,2,6,6-四甲基哌啶 、 正丁基锂 作用下， 生成 2,5-dihydro-2-methyl-1-phenyl-1H-phosphole oxide 、 4-methyl-1-phenyl-2-phospholene 1-oxide
  参考文献：
  名称：

  Alkylation and cyclopentannulation of phospholene derivatives

  摘要：

  The deprotonation of 1-phenyl-3-phospholene I-oxide. I-sulfide or I-borane with I or 2 equiv of LDA, followed by quenching, with electrophiles gave a range of 2-mono- or 2.5-disubstituted phospholene derivatives in good yield. Only trans substitution in relation to the P-Ph group was observed. Treatment of lithiated phospholene intermediates with 1,3-dihaloalkanes afforded annulated 2-phenyl-2phosphabicyclo[3.3.0]oct-3-ene derivatives. The annulation reactions occurred with high regio- and stereoselectivity and led to the exclusive formation of the exo-Ph-P substituted products. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.12.004

文献信息

• Alkylation and cyclopentannulation of phospholene derivatives
  作者：Zbigniew Pakulski、Renata Kwiatosz、K. Michał Pietrusiewicz

  DOI：10.1016/j.tet.2004.12.004

  日期：2005.2

  The deprotonation of 1-phenyl-3-phospholene I-oxide. I-sulfide or I-borane with I or 2 equiv of LDA, followed by quenching, with electrophiles gave a range of 2-mono- or 2.5-disubstituted phospholene derivatives in good yield. Only trans substitution in relation to the P-Ph group was observed. Treatment of lithiated phospholene intermediates with 1,3-dihaloalkanes afforded annulated 2-phenyl-2phosphabicyclo[3.3.0]oct-3-ene derivatives. The annulation reactions occurred with high regio- and stereoselectivity and led to the exclusive formation of the exo-Ph-P substituted products. (C) 2004 Elsevier Ltd. All rights reserved.