2,2-diphenylethyl 4-methylbenzenesulfonate | 6944-27-0

• 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: 2,2-diphenylethyl 4-methylbenzenesulfonate
• CAS: 6944-27-0
• 化学式: C₂₁H₂₀O₃S
• 分子量: 352.454
• InChiKey: FGGIVUNDCMWXPU-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91 °C(Solv: heptane (142-82-5))
• 沸点：
  516.9±39.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-diphenylethyl 4-methylbenzenesulfonate 在 氢氧化钾 、 硫酸 、 sodium 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 25.0h， 生成 4,4-Diphenyl-buttersaeure-methylester
  参考文献：
  名称：

  New 1,3-dioxolane and 1,3-dioxane derivatives as effective modulators to overcome multidrug resistance

  摘要：

  Multidrug resistance (MDR) to antitumor agents represents a major obstacle to a successful chemotherapy of cancer. Overexpression of P-glycoprotein (p-gp) seems to be the major factor responsible for MDR. A large number of chemically unrelated compounds are known to interact with p-gp resulting in a decreasing resistance. In our efforts related to structure-activity studies of new potential MDR reversal agents we synthesized a series of compounds that differ in the aromatic core structure, the linker, and the basic moiety. For our search of new aromatic core structures we synthesized novel 2,2-diphenyl-1,3-dioxolane, 2,2- diphenyl-1,3-dioxane, and 4,5-diphenyl-1,3-dioxolane derivatives. A range of lipophilic linker structures and protonable basic moieties were synthesized and investigated to optimize the structure of the potential MDR-modulators. The compounds were tested in vitro using human Caco-2 cells. Both the cytotoxicity of the synthons and their ability to resensitize the cells were determined with a MTT assay. The results show that at low concentration various substances reverse tumor cell MDR. Some of the new structures show better effects than established modulators like trifluoperazine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.024
• 作为产物：
  描述：

  2,2-二苯基乙酸 在 lithium aluminium tetrahydride 、 硫酸 、 三乙胺 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 33.0h， 生成 2,2-diphenylethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  New 1,3-dioxolane and 1,3-dioxane derivatives as effective modulators to overcome multidrug resistance

  摘要：

  Multidrug resistance (MDR) to antitumor agents represents a major obstacle to a successful chemotherapy of cancer. Overexpression of P-glycoprotein (p-gp) seems to be the major factor responsible for MDR. A large number of chemically unrelated compounds are known to interact with p-gp resulting in a decreasing resistance. In our efforts related to structure-activity studies of new potential MDR reversal agents we synthesized a series of compounds that differ in the aromatic core structure, the linker, and the basic moiety. For our search of new aromatic core structures we synthesized novel 2,2-diphenyl-1,3-dioxolane, 2,2- diphenyl-1,3-dioxane, and 4,5-diphenyl-1,3-dioxolane derivatives. A range of lipophilic linker structures and protonable basic moieties were synthesized and investigated to optimize the structure of the potential MDR-modulators. The compounds were tested in vitro using human Caco-2 cells. Both the cytotoxicity of the synthons and their ability to resensitize the cells were determined with a MTT assay. The results show that at low concentration various substances reverse tumor cell MDR. Some of the new structures show better effects than established modulators like trifluoperazine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.01.024

文献信息

• A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
  作者：Binbin Huang、Lin Guo、Wujiong Xia

  DOI：10.1039/d1gc00317h

  日期：——

  A facile electro-reductive hydrodefunctionalization system employing triethylamine as a sacrificial reductant is described, and the selectivity and capability of reduction can be conveniently switched by simple change of the reaction solvent.

  描述了一种使用三乙胺作为牺牲还原剂的简便电还原去功能化系统，通过简单地改变反应溶剂，可以方便地切换还原的选择性和能力。

• [EN] NOVEL INHIBITORS OF HISTONE DEACETYLASE 10<br/>[FR] NOUVEAUX INHIBITEURS DE L'HISTONE DÉSACÉTYLASE 10
  申请人：DEUTSCHES KREBSFORSCH

  公开号：WO2020193431A1

  公开（公告）日：2020-10-01

  The present invention relates to novel inhibitors of histone deacetylase 10 (HDAC10), novel pharmaceutical compositions comprising such inhibitors, and to novel methods of treating diseases, such as cancer, autoimmune disorders or neurodegeneration, using such novel inhibitors or methods of using such novel inhibitors in organ transplantation.

  本发明涉及新型组蛋白去乙酰化酶10（HDAC10）抑制剂，包括这种抑制剂的新型药物组合物，以及利用这种新型抑制剂治疗疾病（如癌症、自身免疫性疾病或神经退行性疾病）的新方法，或者利用这种新型抑制剂在器官移植中的使用方法。
• Substituent Effect Studies of Aryl-Assisted Solvolyses. I. The Acetolysis of 2,2-Bis(substituted phenyl)ethyl<i>p</i>-Toluenesulfonates
  作者：Mizue Fujio、Yasuyuki Maeda、Mutsuo Goto、Yoshihiro Saeki、Masaaki Mishima、Yuho Tsuno

  DOI：10.1246/bcsj.66.3015

  日期：1993.10

  The substituent effect on the acetolysis of 2,2-bis(substituted phenyl)ethyl p-toluenesulfonates at 90.10 °C can be described accurately in terms of the Yukawa–Tsuno (LArSR) relationship, giving a ρ value of −4.44 and an r value of 0.53. The substituent effect correlation of this system carrying two aryls is quite comparable to that of the 2-methyl-2-phenylpropyl system carrying a single aryl group, suggesting the close similarity in the structure of the transition states between the systems. The results can be reasonably accounted for on the basis of the accepted mechanism of this reaction, involving a rate-determining aryl-assisted transition state where only one aryl group of the two β-aryl groups participates.

  在90.10 °C下，2,2-双（取代苯基）乙基对甲苯磺酸酯的醇解反应中，取代基效应可以通过Yukawa–Tsuno（LArSR）关系进行准确描述，给出了ρ值为−4.44和r值为0.53。该系统中包含两个芳香基的取代基效应与包含单个芳香基的2-甲基-2-苯基丙基系统的相关性相当可比，这表明这两个系统的过渡态结构非常相似。根据这种反应的公认机制，结果可以合理地解释为涉及一个速率决定的芳基辅助过渡态，其中两个β-芳基中的仅一个芳基参与反应。
• Substituent Effect Studies of Aryl-Assisted Solvolyses. II. The Acetolysis of 2-Phenyl-2-(substituted phenyl)ethyl<i>p</i>-Toluenesulfonates
  作者：Mizue Fujio、Yasuyuki Maeda、Mutsuo Goto、Yoshihiro Saeki、Masaaki Mishima、Yuho Tsuno

  DOI：10.1246/bcsj.66.3021

  日期：1993.10

  The substituent effect on the acetolysis of 2-phenyl-2-(substituted phenyl)ethyl p-toluenesulfonates had a nonlinear LArSR correlation and was explicable in terms of a competitive aryl-assisted mechanism involving the X-substituted phenyl-assisted () pathway and the unsubstituted phenyl-assisted () pathway. By the application of the iterative nonlinear least-squares method based on the LArSR Eq., the

  取代基对 2-苯基-2-（取代苯基）乙基对甲苯磺酸酯的乙酰化作用具有非线性 LArSR 相关性，并且可以根据涉及 X 取代苯基辅助 () 途径的竞争性芳基辅助机制进行解释。未取代的苯基辅助 () 途径。通过应用基于 LArSR 方程的迭代非线性最小二乘法，将取代基对整体 kt 的影响分解为 ρM = -3.53 和 rM = 0.60 的最佳拟合 kM 相关性，以及 ρN 的 kN 相关性= -0.88 σ0。辅助芳基取代基效应的 ρM 和 rM 值非常接近于 2-甲基-2-苯丙基体系的值，并且辅助芳基的小 ρN 值与未升高的 σ0 常数与远程 β-芳基效应相容。基于取代基效应分析分析的竞争途径的相对速率与通过 13C-示踪法确定的各个芳基迁移产物的比例完全一致。精确的 ...
• α-Naphthol synthesis via knoevenagel condensation in the presence of molecular sieves
  作者：Giles A. Taylor

  DOI：10.1039/p19810003132

  日期：——

  malonate, ethyl acetoacetate, and ethyl benzoylacetate under Knoevenagel conditions in the presence of molecular sieves to give the 1-naphthols (2), (5), and (6). Glass wool is a less effective catalyst for formation of (2). 3,3-Diethoxycarbonyl-1,1-diphenylpropene (4) is converted into the naphthol (2) in high yield by heating with molecular sieves but its saturated analogue (3) is unaffected.

  在分子筛存在下，在Knoevenagel条件下，二苯乙醛与丙二酸二乙酯，乙酰乙酸乙酯和苯甲酰乙酸乙酯缩合，得到1-萘酚（2），（5）和（6）。玻璃棉是形成（2）的不太有效的催化剂。通过与分子筛加热，将3，3-二乙氧基羰基-1，1-二苯基丙烯（4）以高收率转化为萘酚（2），但其饱和类似物（3）不受影响。