1,1,1-三苯基丁烷 | 43044-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 1,1,1-三苯基丁烷
• 英文名称: 1,1,1-triphenylbutane
• 英文别名: 1,1,1-triphenyl-butane；1,1,1-Triphenyl-butan；Propyltriphenylmethan；1,1,1-Triphenylbutan；Triphenylbutane；1,1-diphenylbutylbenzene
• CAS: 43044-69-5
• 化学式: C₂₂H₂₂
• 分子量: 286.417
• InChiKey: BQULNJDDNPKMKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  59 °C
• 沸点：
  393.7±22.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,1,1-三苯基丁烷 在 双氧水 、 戴斯-马丁氧化剂 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 9.83h， 生成 4,4,4-triphenylbutanal
  参考文献：
  名称：

  Triphenylbutanamines: Kinesin Spindle Protein Inhibitors with in Vivo Antitumor Activity

  摘要：

  The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-L-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit K-i(aPP) <= 10 nM and GI(50) approximate to 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.

  DOI：

  10.1021/jm201195m
• 作为产物：
  描述：

  4,4,4-三苯基-1-丁烯 在 sodium tetrahydroborate 、 硫酸 作用下， 以 乙醚 、 二乙二醇二甲醚 为溶剂， 反应 5.0h， 生成 1,1,1-三苯基丁烷
  参考文献：
  名称：

  Triphenylbutanamines: Kinesin Spindle Protein Inhibitors with in Vivo Antitumor Activity

  摘要：

  The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-L-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit K-i(aPP) <= 10 nM and GI(50) approximate to 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.

  DOI：

  10.1021/jm201195m

文献信息

• Solov'yanov, A. A.; Karpyuk, A. D.; Beletskaya, I. P., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 2, p. 381 - 389
  作者：Solov'yanov, A. A.、Karpyuk, A. D.、Beletskaya, I. P.、Reutov, O. A.

  DOI：——

  日期：——
• Reactions of Triphenylmethylmagnesium Bromide. II
  作者：W. E. Bachmann、R. F. Cockerill

  DOI：10.1021/ja01334a051

  日期：1933.7
• Carbanions. XI. Reactions of 4-chloro-1,1,1-triphenylbutane, 5-chloro-1,1,1-triphenylpentane, and 1,1,1-triphenylethane with alkali metals. 1,4 and 1,5 Migration of phenyl
  作者：Erling Grovenstein、James A. Beres、Yao-Ming Cheng、James A. Pegolotti

  DOI：10.1021/jo00974a001

  日期：1972.5
• Gomberg; Cone, Chemische Berichte, 1906, vol. 39, p. 2961
  作者：Gomberg、Cone

  DOI：——

  日期：——
• LARPENT, CHANTAL;LE, MENN FRANCOISE BRISSE;PATIN, HENRI, C. R. ACAD. SCI. SER. 2, 308,(1989) N, C. 615-619
  作者：LARPENT, CHANTAL、LE, MENN FRANCOISE BRISSE、PATIN, HENRI

  DOI：——

  日期：——