1-Chloro-4-methyl-5,6,7,8-tetrahydro-2-phosphanaphthalene | 144284-80-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 金属杂环化合物
• 英文名称: 1-Chloro-4-methyl-5,6,7,8-tetrahydro-2-phosphanaphthalene
• 英文别名: 1-Chloro-4-methyl-5,6,7,8-tetrahydroisophosphinoline
• CAS: 144284-80-0
• 化学式: C₁₀H₁₂ClP
• 分子量: 198.632
• InChiKey: FYEMEQZPKCXDGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (二氯甲基)亚膦酸二氯化物 、 1-(1-methylethenyl)cyclohexene 在 三乙胺 作用下， 生成 1-Chloro-4-methyl-5,6,7,8-tetrahydro-2-phosphanaphthalene
  参考文献：
  名称：

  Teunissen, Herman T.; Bickelhaupt, Friedrich, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 7, p. 609 - 616

  摘要：

  DOI：

文献信息

• Diels-Alder Reactions of Trichlorophosphaethene
  作者：Herman T. Teunissen、Jan Hollebeek、Peter J. Nieuwenhuizen、Ben L. M. van Baar、Frans J. J. de Kanter、Friedrich Bickelhaupt

  DOI：10.1021/jo00128a015

  日期：1995.11

  The Diels-Alder reactions of trichlorophosphaethene (3), generated in situ from dichloro(dichloromethyl)phosphine (2), with 1-vinylnaphthalene (6), 1-(1-methylethenyl)cyclohexene (4), and 1-[1-(trimethylsiloxy)ethenyl]cyclohexene (13) at 60-75 degrees C, are described. The reactions of 3 with 4 and 6 afforded, after aromatization of the primary Diels-Alder adducts 5 and 8 under the influence of triethylamine, the 2-chlorophosphinines 9 and 11, respectively. The reaction with 13, however, led to the formation of the ''double adduct'' 16, which could not be isolated in pure form. The formation of the ''double adduct'' is explained by a subsequent Diels-Alder reaction of 13 with dihydrophosphinine 15, which is formed after HCl elimination from the primary Diels-Alder adduct 14. The reaction of 13 with 23, the pentacarbonyltungsten complex of 2, furnished 27, the pentacarbonyltungsten complex of 16, which was isolated in pure form. The regiochemistry of the Diels-Alder reactions described above is discussed on the basis of MNDO/PM3 calculations of the frontier molecular orbital coefficients. The Diels-Alder reactions proceed with normal electron demand, and the experimentally observed regiochemistry is in accordance with theoretical predictions. The formation of the ''double adducts'' 16 and 27 is rationalized as a consequence of the high HOMO energy of 13 compared with that of 4.
• Teunissen, Herman T.; Bickelhaupt, Friedrich, Bulletin des Societes Chimiques Belges, 1992, vol. 101, # 7, p. 609 - 616
  作者：Teunissen, Herman T.、Bickelhaupt, Friedrich

  DOI：——

  日期：——