4,6-bis(tert-butyl)-2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole | 88093-18-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 4,6-bis(tert-butyl)-2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole
• 英文别名: 4,6-di-tert-butyl-2,2,2-trichloro-1,3,2λ⁵-benzodioxaphosphole；3,5-di(tert-butyl)-2,2,2-trichlorobenzo-1,3,2-dioxaphosphole；4,6-Bis(t-butyl)-2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole；4,6-ditert-butyl-2,2,2-trichloro-1,3,2λ5-benzodioxaphosphole
• CAS: 88093-18-9
• 化学式: C₁₄H₂₀Cl₃O₂P
• 分子量: 357.644
• InChiKey: FMZMBLVNKJTCLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,6-bis(tert-butyl)-2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole 在 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 3,5-di-tert-butyl-1,2-phenylene chlorophosphate
  参考文献：
  名称：

  Akhrem, A. A.; Dolgopalets, V. I.; Kisel, M. A., Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 5, p. 337 - 340

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二叔丁基邻苯二酚 在 五氯化磷 作用下， 以 苯 为溶剂， 以65%的产率得到4,6-bis(tert-butyl)-2,2,2-trichlorobenzo[d]-1,3,2-dioxaphosphole
  参考文献：
  名称：

  摘要：

  The reaction of 4,6-bis(tert-butyl) - 2,2,2 -trichlorobenzo[d] - 1, 3.2 -dioxaphosphole with phenylacetylene follows the mechanism of ipso-substitution of the tert-butyl group that is in para-position relative to the endocyclic O atom of the heterocycle, predominantly yielding 8-(tert-butyl)-2,6-dichloro-2-oxo-4-phenylbenzo[e]-1,2-oxaphosphorinine (NMR data). The structure of its hydrolysis product, 8-(tert-butyl)-6-chloro-2-hydroxy-2-oxo-4-phenylbenzo[e]-1,2-oxaphosphorinine, was proved by X-ray diffraction analysis.

  DOI：

  10.1023/a:1011377231921

文献信息

• The New Data for the Reaction of Arylenedioxy Trihalogenophosphoranes with Alkyl- and Arylacetylenes
  作者：Vladimir F. Mironov、Alfiya A. Shtyrlina、Ravil R. Petrov、Tamara A. Baronova、Fedor F. Alekseev、Elena N. Varaksina、Aleksander I. Konovalov

  DOI：10.1080/10426500212243

  日期：2002.6.1

  halogenation regiochemistry are discussed. The ipso -substitution of tert -butyl group on chlorine and the exchange of bromine on chlorine and iodine on hydrogen have been observed, along with formation of benzophosphorines. The interaction of tetrachloro- ortho -benzoquinone with phosphorus trichloride and arylacetylenes is proposed as a new modification of the reaction leading to the formation of benzo[ e ]-1

  总结了有关取代的亚芳基二氧基三卤代正膦与单烷基或芳基乙炔之间反应的新数据。该反应导致形成六元杂环-2-oxo-4-R-benzo[e]-1,2-oxaphosphorin-3-enes。讨论了正膦和乙炔分子中的取代基对本位取代和卤化区域化学的影响。已经观察到氯上叔丁基的同位取代和氯上溴和氢上碘的交换，以及苯并膦的形成。四氯邻苯醌与三氯化磷和芳基乙炔的相互作用被提议作为导致形成苯并[e]-1,2-氧杂磷的反应的新改进。一些苯并[e]-1的结构，
• Reactions of 3,5-di(tert-butyl)-1,2-benzoquinone with terminal acetylenes in the presence of phosphorus trichloride. ipso-Substitution of the tert-butyl group
  作者：V. F. Mironov、A. V. Bogdanov、A. V. Nemtarev、A. A. Shtyrlina、E. N. Varaksina、V. K. Cherkasov、A. B. Dobrynin、D. B. Krivolapov、R. Z. Musin、I. A. Litvinov、A. I. Konovalov

  DOI：10.1007/s11172-007-0292-9

  日期：2007.9

  The reactions of 3,5-di(tert-butyl)-1,2-benzoquinone with aryl-and alkylacetylenes in the presence of phosphorus trichloride afford 4-aryl(alkyl)-8-tert-butyl-2,6-dichloro-2-oxo-2H-benzo[e][1,2]oxaphosphinines as the major ipso-substitution products of the tert-butyl group by the chlorine atom. 4-Aryl(alkyl)-6,8-di(tert-butyl)-2,5-dichloro-2-oxo-and 4-aryl(alkyl)-6-tert-butyl-2,8-dichloro-2-oxo-2H-benzo[e][1

  3,5-二(叔丁基)-1,2-苯醌与芳基-和烷基乙炔在三氯化磷存在下反应得到4-芳基(烷基)-8-叔丁基-2,6-二氯- 2-氧代-2H-苯并[e][1,2]氧代膦作为叔丁基被氯原子的主要同位取代产物。4-芳基(烷基)-6,8-二(叔丁基)-2,5-二氯-2-氧代-和4-芳基(烷基)-6-叔丁基-2,8-二氯-2-得到氧代-2H-苯并[e][1,2]氧代膦作为次要产物。该系列稳定代表的结构由 X 射线衍射证实。
• Studies of the oxidation of elemental phosphorus by substituted ortho-benzoquinones
  作者：Theodore A. Annan、Zhigang Tian、Dennis G. Tuck

  DOI：10.1039/dt9910000019

  日期：——

  The phosphorus compounds P(O2C6R)2Br (R = Cl4, Br4 or Bu2H2) have been prepared by the reaction of P4, Br2 and the substituted o-benzoquinone RC6O2-o. There is no reaction between Bu2H2C6O2-o, P4 and Ph2Se2, but in the presence of catalytic quantities of Br2 the product is P(O2C6H2Bu2)2(SePh). ESR spectra identify the presence of the corresponding o-semiquinone species in these reactions. The C-13 and P-31 NMR spectra of these phosphoranes are reported, and compared with those of P(O2C6R)X3 (X3 = Ph3, Ph2Cl, Br3 or Cl3) prepared by the reaction of PX3 and RC6O2-o.
• Klimov, E. S.; Bumber, A. A.; Okhlobystin, O. Yu., Journal of general chemistry of the USSR, 1983, vol. 53, # 8, p. 1565 - 1567
  作者：Klimov, E. S.、Bumber, A. A.、Okhlobystin, O. Yu.

  DOI：——

  日期：——
• Regioselectivity of the reaction of 4,6-di-tert-butyl-2,2,2-trichloro-1,3,2λ5-benzodioxaphosphole with hex-1-yne. ipso substitution of tert-butyl group
  作者：A. V. Nemtarev、E. N. Varaksina、V. F. Mironov、R. Z. Musin、A. I. Konovalov

  DOI：10.1134/s1070428007110280

  日期：2007.11