4-tert-butyl-1-cyclohexyl-6-(4-methoxyphenyl)-N,N-di(propan-2-yl)-1,3,2-diazaphosphinin-2-amine | 177651-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-tert-butyl-1-cyclohexyl-6-(4-methoxyphenyl)-N,N-di(propan-2-yl)-1,3,2-diazaphosphinin-2-amine
• CAS: 177651-32-0
• 化学式: C₂₆H₄₂N₃OP
• 分子量: 443.613
• InChiKey: JAKDCRIRWGUEAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  28.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-1-cyclohexyl-6-(4-methoxyphenyl)-N,N-di(propan-2-yl)-1,3,2-diazaphosphinin-2-amine 在 二氟氯乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Reactivity of dihydrodiazaphosphinines towards unsaturated substrates: Addition, [5 + 2] cycloaddition and rearrangement processes

  摘要：

  Treatment of 4-amino-1-azadienes 1 with dichloro (diisopropylamino)phosphane gave 1,2-dihydro- 1,3,2-diazaphosphinines 3, which cycloadded in a [5 + 2] fashion to dimethyl acetylenedicarboxylate to furnish bicyclic iminophosphoranes 5. The single addition compound 6 was formed by reaction of 3a with (CO)(5)Cr=C(OMe)(C equivalent to CPh). Compounds 5 underwent formal 1,7-rearrangement to 7 at room temperature. In turn, 5a reacted with electrophiles (difluorochloroacetic acid and methyl iodide) through the valence isomer 5a' to give polycyclic structures 13 and 14, which led to 16 by fluoride-induced [4 + 2] cycloreversion. Other reactive electrophilic substrates, Like diethyl azodicarboxylate and N-phenyltriazolinedione, led to the oxidized derivative 9 and to the addition product 12 respectively. The X-ray structures of 7a and 12 are discussed.

  DOI：

  10.1016/s0022-328x(96)06618-1
• 作为产物：
  描述：

  二氯-N,N-二异丙基亚磷酰胺 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以94%的产率得到4-tert-butyl-1-cyclohexyl-6-(4-methoxyphenyl)-N,N-di(propan-2-yl)-1,3,2-diazaphosphinin-2-amine
  参考文献：
  名称：

  Barluenga, Jose; Tomas, Miguel; Bieger, Klaus, Angewandte Chemie, 1996, vol. 108, # 8, p. 977 - 979

  摘要：

  DOI：

文献信息

• Reaction of Dihydrodiazaphosphinines with Acetylenic Diesters: A Direct Synthesis of the λ5-Diazaphosphaazulene Skeleton
  作者：José Barluenga、Miguel Tomás、Klaus Bieger、Santiago García-Granda、Rafael Santiago-García

  DOI：10.1002/(sici)1099-0690(199807)1998:7<1425::aid-ejoc1425>3.0.co;2-0

  日期：1998.7

  depending on the reaction conditions. Compound 6a is alternatively synthesized by treatment of equimolecular amounts of the previously described monoadduct 3(3′) and dimethyl acetylenedicarboxylate. A reaction pathway is proposed based primarily on i) the isolation and characterization of intermediate 8(8′) and ii) the reactivity of 3(3′) towards electrophiles, in particular with tetracyanoethylene (compound

  根据反应条件，1,2-二氢-1,3,2-二氮杂膦2与乙炔-二羧酸酯反应生成化学选择性的加合物5或6a，b。或者，通过等摩尔量的前述单加合物3（3'）和乙炔二羧酸二甲酯的处理来合成化合物6a。提出的反应途径主要基于以下方面：i）中间体8（8'）的分离和表征，以及ii）3（3'）对亲电试剂，特别是四氰基乙烯（化合物10）的反应性）。
• Barluenga, Jose; Tomas, Miguel; Bieger, Klaus, Angewandte Chemie, 1996, vol. 108, # 8, p. 977 - 979
  作者：Barluenga, Jose、Tomas, Miguel、Bieger, Klaus、Garcia-Granda, Santiago、Santiago-Garcia, Rafael

  DOI：——

  日期：——
• C38H54N3O9P, a New Compound in Diazadihydrophosphinine Chemistry
  作者：S. García-Granda、R. Santiago-García、K. Bieger

  DOI：10.1107/s0108270196007755

  日期：1996.11.15

  Another compound of the diazadihydrophosphinine family has been isolated and structurally characterized. This new compound in diazadihydrophosphinine chemistry was identified as trimethyl 5-[4-tert-butyl-1-cyclohexyl-2-diisopropylamino-6-(4-methoxyphenyl)-1,2-dihydrol-1,3,2-diazaphosphin-2-ylidene]-3-methoxy4-oxo-1-cyclo-pentene-1,2,3-tricarboxylate, C38H54N3O9P. The parent dihydrodiazaphosphin structure is still present in the new compound and the P atom is linked by a double bond to a five-membered ring. The P(1)-C(31) bond distance is 1.731(8) Angstrom. The five-membered ring is planar [maximum deviation from the least-squares plane of 0.011 (9) Angstrom for C(35)] and the ylidic charge at C alpha to the P atom is stabilized by the electron-attracting groups in the ring.
• Reactivity of dihydrodiazaphosphinines towards unsaturated substrates: Addition, [5 + 2] cycloaddition and rearrangement processes
  作者：José Barluenga、Miguel Tomás、Klaus Bieger、Santiago García-Granda、Rafael Santiago-García

  DOI：10.1016/s0022-328x(96)06618-1

  日期：1997.2

  Treatment of 4-amino-1-azadienes 1 with dichloro (diisopropylamino)phosphane gave 1,2-dihydro- 1,3,2-diazaphosphinines 3, which cycloadded in a [5 + 2] fashion to dimethyl acetylenedicarboxylate to furnish bicyclic iminophosphoranes 5. The single addition compound 6 was formed by reaction of 3a with (CO)(5)Cr=C(OMe)(C equivalent to CPh). Compounds 5 underwent formal 1,7-rearrangement to 7 at room temperature. In turn, 5a reacted with electrophiles (difluorochloroacetic acid and methyl iodide) through the valence isomer 5a' to give polycyclic structures 13 and 14, which led to 16 by fluoride-induced [4 + 2] cycloreversion. Other reactive electrophilic substrates, Like diethyl azodicarboxylate and N-phenyltriazolinedione, led to the oxidized derivative 9 and to the addition product 12 respectively. The X-ray structures of 7a and 12 are discussed.