bis(4-((tert-butyldimethylsilyl)oxy)phenyl)methanone | 111983-37-0

• 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(4-((tert-butyldimethylsilyl)oxy)phenyl)methanone
• 英文别名: 4,4'-di(tert-butyldimethylsilyloxy)benzophenone；4,4'-bis(tertbutyldimethylsilyloxy)benzophenone；Bis(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)methanone；bis[4-[tert-butyl(dimethyl)silyl]oxyphenyl]methanone
• CAS: 111983-37-0
• 化学式: C₂₅H₃₈O₃Si₂
• 分子量: 442.746
• InChiKey: YNLHRGSTDIHBGS-UHFFFAOYSA-N

物化性质

• 沸点：
  455.9±30.0 °C(Predicted)
• 密度：
  0.979±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(4-((tert-butyldimethylsilyl)oxy)phenyl)methanone 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 1-cyclohexyl-1,1-bis(4-hydroxyphenyl)methanol
  参考文献：
  名称：

  Synthesis, in vitro and in vivo activity of benzophenone-based inhibitors of steroid sulfatase

  摘要：

  Steroid sulfatase (STS) is all important new therapeutic target in oncology. Attempts to design nonsteroidal STS inhibitors, because of the oestrogenicity of the original lead oestrone 3-O-sulfamate in rodents, have led to the discovery of benzophenone-4,4'-O,O-bis-sulfamate (BENZOMATE, 3). The nonfused bicyclic BENZOMATE is a highly potent STS inhibitor in vitro, inhibiting STS activity in intact MCF-7 breast cancer cells by >70% at 0.1 muM and in placental microsomes by >98% at 10 mum. When MCF-7 cells were pre-treated with 3 at 1 muM and then washed to remove unbound inhibitor, the initial 94% inhibition was reduced to 89% suggesting that 3, like other sulfamate-based STS inhibitors, inhibits the enzyme irreversibly. This agent also inhibits rat liver STS activity by 84% and 93% respectively 24 h after a single dose of 1 or 10 mg/kg, demonstrating that BENZOMATE possesses similar in Vivo potency to the established potent nonsteroidal inhibitor 667COUMATE. Several modifications were made to BENZOMATE structurally and effects on in vitro activity were examined. These structure-activity relationship studies show that its carbonyl and bis-sulfamate groups are pivotal for activity, although conformational flexibility is not required. Two rigid anthraquinone-based sulfamate derivatives however showed inhibitory activity significantly better than BENZOMATE in the MCF-7 cell assay. BENZOMATE and related analogues therefore represent all important class of non-steroidal STS inhibitor and lead compounds for future drug design. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.040
• 作为产物：
  描述：

  在 (R,R)-Jacobsen catalyst 、 三乙氧基硅烷 作用下， 以 甲苯 为溶剂， 以92 %的产率得到bis(4-((tert-butyldimethylsilyl)oxy)phenyl)methanone
  参考文献：
  名称：

  通过共催化氢原子转移对烯丙醇进行有氧 C-C 键断裂

  摘要：

  已经开发出一种简单、有效的方法，用于 Co III -H 催化的叔烯丙醇的有氧 C-C 键裂解以获得酮。这种新方法具有出色的化学选择性、良好的官能团相容性和高产率。该反应通过 HAT 引发的过氧化物中间体发生，建议使用相邻的乙二醇型双自由基裂解过程。

  DOI：

  10.1021/acs.orglett.3c00556

文献信息

• Synthesis and Biological Evaluation of 1-(Diarylmethyl)-1H-1,2,4-triazoles and 1-(Diarylmethyl)-1H-imidazoles as a Novel Class of Anti-Mitotic Agent for Activity in Breast Cancer
  作者：Gloria Ana、Patrick M. Kelly、Azizah M. Malebari、Sara Noorani、Seema M. Nathwani、Brendan Twamley、Darren Fayne、Niamh M. O’Boyle、Daniela M. Zisterer、Elisangela Flavia Pimentel、Denise Coutinho Endringer、Mary J. Meegan

  DOI：10.3390/ph14020169

  日期：——

  We report the synthesis and biochemical evaluation of compounds that are designed as hybrids of the microtubule targeting benzophenone phenstatin and the aromatase inhibitor letrozole. A preliminary screening in estrogen receptor (ER)-positive MCF-7 breast cancer cells identified 5-((2H-1,2,3-triazol-1-yl)(3,4,5-trimethoxyphenyl)methyl)-2-methoxyphenol 24 as a potent antiproliferative compound with

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  DOI：10.1021/acs.joc.6b01361

  日期：2016.9.2

  merocyanine dyes with high molar absorptivities to permit naked-eye sensing. The absorption spectral shifts, i.e., differences in the absorption maxima of colorless and colored forms, observed for a rationally designed set of silyloxy-substituted diarylpyrans subsequent to fluoride-induced ring opening are remarkably high (330–480 nm), and are unknown for any colorimetric probe. In particular, the disilyloxy-substituted

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  DOI：10.1246/cl.170211

  日期：2017.6.5

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  DOI：10.1002/anie.201609939

  日期：2017.1.19

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• SuFEx-Based Synthesis of Polysulfates
  作者：Jiajia Dong、K. Barry Sharpless、Luke Kwisnek、James S. Oakdale、Valery V. Fokin

  DOI：10.1002/anie.201403758

  日期：2014.9.1

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