3,3-bis(trifluoromethyl)-1-(4-methylphenyl)-3H-2,1-banzoxastibole | 156606-81-4

• 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-(4-methylphenyl)-3H-2,1-banzoxastibole
• 英文别名: 1-(4-methylphenyl)-3,3-bis(trifluromethyl)-3H-2,1-benzoxastibole
• CAS: 156606-81-4
• 化学式: C₁₆H₁₁F₆OSb
• 分子量: 455.003
• InChiKey: FUCXASYTCLIGKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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-(4-methylphenyl)-3H-2,1-banzoxastibole 以 乙醚 为溶剂， 生成 1-(2,6-bis[(dimethylamino)methyl]phenyl)-3,3-bis(trifluoromethyl)-3H-2,1-benzoxastibole
  参考文献：
  名称：

  Yamamoto, Yohsuke; Chen, Xiang; Kojima, Satoshi, Journal of the American Chemical Society, 1995, vol. 117, # 14, p. 3922 - 3932

  摘要：

  DOI：
• 作为产物：
  描述：

  lithium 1,1,1,3,3,3-hexafluoro-2-(2-lithiophenyl)-2-propoxide 、 dichloro(4-methylphenyl)stibine 在 H₂O 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到3,3-bis(trifluoromethyl)-1-(4-methylphenyl)-3H-2,1-banzoxastibole
  参考文献：
  名称：

  Yamamoto, Yohsuke; Chen, Xiang; Kojima, Satoshi, Journal of the American Chemical Society, 1995, vol. 117, # 14, p. 3922 - 3932

  摘要：

  DOI：

文献信息

• Evidence for Intramolecular Permutation (Pseudorotation) at the Central Antimony Atom and Strong Equatophilicity of an Iron and a Ruthenium Ligand in Pentacoordinate Hypervalent Antimony Compounds
  作者：Koichiro Toyota、Yukiya Wakisaka、Yohsuke Yamamoto、Kin-ya Akiba

  DOI：10.1021/om000790l

  日期：2000.11.1

  bond 4a and 4b:  RfRfm*Sb*FeCp(CO)2 Rf = o-C6H4C(CF3)2O-, Rfm* = o-C6H4C*(CF3)(Me)O-} were synthesized by the reaction of stiboranide anion, RfRfm*Sb*-Li+ (3-Li), with CpFeI(CO)2 in the presence of AgBF4. The carbonyl group of 4 was replaced with triphenylphosphine by irradiation with a tungten lamp to give a mixture of four diastereomers 5a−5d:  RfRfm*Sb*Fe*Cp(CO)(PPh3)}. Each of the diastereomers

  具有Sb-Fe键 4a和4b的非对映异构五价高价甾烷烃：RfRfm * Sb * FeCp（CO）2 Rf = o -C 6 H 4 C（CF 3）2 O-，Rfm * = o -C 6 H 4 C *（CF 3）（Me）的O-}通过stiboranide阴离子的反应合成，RfRfm *锑* -李+（3-锂）中，用CpFeI（CO）2中的AgBF的存在4。4的羰基用钨灯照射，用三苯膦代替三苯基膦，得到四种非对映异构体的混合物 5a - 5d：RfRfm * Sb * Fe * Cp（CO）（PPh 3）}。通过TLC分离各非对映异构体，并通过X射线晶体学分析确定相对立体化学。来自纯非对映异构体5的热平衡表明，异构化是通过中心锑原子的转化（伪旋转）发生的。5的伪旋转势垒比Rf 2 Sb * Cl和RfRfm * Sb *（p -CH 3 C 6 H 4）。这些结果与第8族过渡金属片段的电子给体性质一致。高价西bor烷
• First Stereochemical Characterization of Configurationally Stable Diastereomers of Hypervalent Stiboranes (10-Sb-5) and Acceleration of Intramolecular Permutation by Donor Solvents
  作者：Satoshi Kojima、Yasutaka Doi、Manabu Okuda、Kin-ya Akiba

  DOI：10.1021/om00004a053

  日期：1995.4

  The first stereochemical characterization of a pair of configurationally stable diastereomeric 10-Sb-5 compounds (o-0(CF3)(CH3)C*C6H4)(o-0(CF3)(2)C6H4)Sb*(p-C6H4CH3) with an asymmetric antimony atom was accomplished by NOE differential spectra and confirmed by the X-ray analysis of the major diastereomer 6a. Kinetic measurements of the interconversion between the major diastereomer 6a and the minor diastereomer 6b were carried out in 10 different solvents, and it was found that the process was intramolecular and protonation was not an essential factor. The rates were accelerated in polar solvents, and the activation ethalpy (Delta H-double dagger ) decreased from 26.1 to 23.5 kcal mol(-1) changing the E(T)(N) values from 0.012 (n-octane) to 0.327 (1,2-dichloroethane) while the donor numers DNN were kept to almost zero. Larger acceleration of the rates was observed in donor solvents, and this is apparent by comparing the Delta H-double dagger values of pairs of solvents with different DNN values and similar E(T)(N) values, i.e., ethyl propionate (21.3) and o-dichlorobenzene (24.9); pyridine (17.3) and 1,2-dichloroethane (23.5). This is rationalized by invoking a hexacoordinate transition state.