3,3-bis(trifluoromethyl)-1-(p-(trifluoromethyl)phrnyl)-1,1-bis(p-methylphenyl)-3H-2,1-benzoxabismole | 121959-25-9

• 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: 3,3-bis(trifluoromethyl)-1-(p-(trifluoromethyl)phrnyl)-1,1-bis(p-methylphenyl)-3H-2,1-benzoxabismole
• 英文别名: 1,1-bis(4-methylphenyl)-3,3-bis(trifluoromethyl)-1-[4-(trifluoromethyl)phenyl]-2,1λ5-benzoxabismole
• CAS: 121959-25-9
• 化学式: C₃₀H₂₂BiF₉O
• 分子量: 778.47
• InChiKey: HLAIBCWJALDGLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  41.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  3,3-bis(trifluoromethyl)-1-(p-(trifluoromethyl)phrnyl)-1,1-bis(p-methylphenyl)-3H-2,1-benzoxabismole 、 磺酰氯 生成 3,3-bis(trifluoromethyl)-1-chloro-1-(p-(trifluoromethyl)phenyl)-1-(p-methylphenyl)-3H-2,1-benzoxabismole
  参考文献：
  名称：

  AKIBA, KIN-YA;OHDOI, KEISUKE;YAMAMOTO, YOHSUKE, TETRAHEDRON LETT., 29,(1988) N 31, C. 3817-3820

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3-bis(trifluoromethyl)-1-chloro-1,1-bis(p-methylphenyl)-3H-2,1-benzoxabismole 、 (4-trifluoromethylphenyl)lithium 在 NaCl 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到3,3-bis(trifluoromethyl)-1-(p-(trifluoromethyl)phrnyl)-1,1-bis(p-methylphenyl)-3H-2,1-benzoxabismole
  参考文献：
  名称：

  高价有机铋化合物（10-Bi-5）的合成，卤解和晶体结构

  摘要：

  The stable 10-Bi-5 compounds (o-C6H4C(CF3)20)BiAr2R(3(Ar,R): 3a,p-CH3CrH4,p-CH3C6H4; 3b, P-CF3C6H4, p-CF3C6H4; 3c, p-FC6H4, p-FC6H4; 3d, p-CH3C6H4, p-CF3C6H4; 3e, p-CF3C6H4, p-CH3C6H4;3f,p-CH3Cr6H4,PhC=C;3g,p-CH3C6H4,Me) were synthesized. The X-ray structures of 3a,fg showed distorted-trigonal-bipyramidal geometries, and the electronegative apical PhC=C ligand of 3f made the apical Bi-O bond (2.243(3) angstrom) shorter than the Bi-O bond of 3a,g (2.323(4) angstrom in 3a and 2.328(7) angstrom in 3g). Halogenolysis of 3 with sulfuryl chloride or pyridinium bromide perbromide gave the five-coordinate bismuth compounds (o-C6H4C(CF3)20)BiArlAr2X (6 (Ar1, Ar2, X): 6a,p-CH3C6H4,p-CH3C6H4,Cl;6b,p-CF3C6H4,p-CF3C6H4,Cl;6c,p-FC6H4, p-FC6H4, Cl; 6d, p-CH3C6H4, p-CH3C6H4, Br; 6e, p-CH3C6H4, p-CF3C6H4, Cl; 6f, p-CH3C6H4, p-CF3C6H4, Br) in good to quantitative yield with apical covalent Bi-halogen bonds which were clearly shown by the X-ray analysis of 6a,b,d,e. The reactivity order of 3 for the halogenolysis was as follows: PhC=C-Bi > Me-Bi > p-CH3CrH4-Bi > p-CF3C6H4-Bi. Direct halogenolysis of the bismuth-carbon bond was suggested. The variable-temperature F-19 NMR of unsymmetrically substituted 6e,f did not show coalescence of the CF3 groups up to 170-degrees-C in a dilute solution of toluene-d8, and the energies of inversion at the bismuth atom should be higher than 21 kcal mol-1 at 170-degrees-C.

  DOI：

  10.1021/om00029a047