bis(2,6-dimethylphenyl)methyl chloride | 36462-24-5

• 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: bis(2,6-dimethylphenyl)methyl chloride
• 英文别名: 2,6,2',6'-tetramethyl-benzhydryl chloride；2-[Chloro-(2,6-dimethylphenyl)methyl]-1,3-dimethylbenzene
• CAS: 36462-24-5
• 化学式: C₁₇H₁₉Cl
• 分子量: 258.791
• InChiKey: JTIAHFXPVDVMQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  369.8±11.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  bis(2,6-dimethylphenyl)methyl chloride 在 盐酸 、 3 A molecular sieve 、 氨 、 氢气 、 镍 、 sodium cyanoborohydride 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 25.0~80.0 ℃ 、6.08 MPa 条件下， 反应 30.5h， 生成 N,N'-Diallyl-6-{4-[2,2-bis-(2,6-dimethyl-phenyl)-ethylamino]-piperidin-1-yl}-[1,3,5]triazine-2,4-diamine
  参考文献：
  名称：

  New triazine derivatives as potent modulators of multidrug resistance

  摘要：

  A series of 70 triazine derivatives have been synthesized and tested for their capacity to modulate multidrug resistance (MDR) in DC-3F/AD and KB-A1 tumor cells in vitro, in comparison with verapamil (VRP), a calcium channel antagonist currently used in therapy as an antihypertensive drug, which also shows MDR modulating activity. Among the 12 selected compounds, 16 (S9788) showed high MDR reversing properties in vitro (300- and 6-fold VRP at 5-mu-M in DC-3F/AD and KB-A1 cells, respectively) and induced a strong accumulation of adriamycin. The relationship between the increase of ADR accumulation and the fold reversal induced by these compounds and their lack of effects on the sensitive DC-3F cells suggest that they act mainly by inhibiting the P-glycoprotein (Pgp) catalyzed efflux of cytotoxic agents, as already described for a majority of MDR modulators. In vivo, in association with the antitumor drug vincristine (0.25 mg/kg), 16 (100 mg/kg) increased the TIC by 39% in mice bearing the resistant tumor cell line P388/VCR. According to these interesting properties, 16 was selected for a clinical development because it was more bioavailable than 34, even though it was less active.

  DOI：

  10.1021/jm00091a017
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 苯 作用下， 生成 bis(2,6-dimethylphenyl)methyl chloride
  参考文献：
  名称：

  Coops et al., Recueil des Travaux Chimiques des Pays-Bas, 1940, vol. 59, p. 1109,1111

  摘要：

  DOI：

文献信息

• The Effects of Alkyl Substitution in Drugs--I. Substituted Dimethylaminoethyl Benzhydryl Ethers
  作者：A. F. Harms、W. Th. Nauta

  DOI：10.1021/jm50008a005

  日期：1960.2
• Bolton, Roger; Burley, Rita E.; Williams, Nigel J., Australian Journal of Chemistry, 1986, vol. 39, # 4, p. 625 - 634
  作者：Bolton, Roger、Burley, Rita E.、Williams, Nigel J.

  DOI：——

  日期：——
• Nauta; Ernsting; Faber, Recueil des Travaux Chimiques des Pays-Bas, 1941, vol. 60, p. 915,927
  作者：Nauta、Ernsting、Faber

  DOI：——

  日期：——
• Fleurke,K.H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1965, vol. 84, p. 1380 - 1385
  作者：Fleurke,K.H. et al.

  DOI：——

  日期：——
• Stereochemistry of dimesityl-9-anthrylmethane and bis(2,6-xylyl)-1-(2-methylnaphthyl)methane. Evidence for the two-ring flip mechanism in triarylmethanes
  作者：Paolo Finocchiaro、Devens Gust、Kurt Mislow

  DOI：10.1021/ja00814a030

  日期：1974.4