1,1'-(2,3-Dimethylbutane-2,3-diyl)bis(3,4-dimethoxybenzene) | 74385-24-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,1'-(2,3-Dimethylbutane-2,3-diyl)bis(3,4-dimethoxybenzene)
• 英文别名: 4-[3-(3,4-dimethoxyphenyl)-2,3-dimethylbutan-2-yl]-1,2-dimethoxybenzene
• CAS: 74385-24-3
• 化学式: C₂₂H₃₀O₄
• 分子量: 358.478
• InChiKey: OLKCFWNHVUUHGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1'-(2,3-Dimethylbutane-2,3-diyl)bis(3,4-dimethoxybenzene) 在 吡啶 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 生成 2,3-bis(3',4'-diacetoxyphenyl)-2,3-dimethylbutane
  参考文献：
  名称：

  Antiestrogens. Synthesis and evaluation of mammary tumor inhibiting activity of 1,1,2,2-tetraalkyl-1,2-diphenylethanes

  摘要：

  Among the newly synthesized 1,1,2,2-tetraalkyl-1,2-diphenylethanes, 1,1,2,2-tetramethyl-1,2-bis(4'-hydroxyphenyl)ethane (23) and 1,1,2,2-tetramethyl-1,2-bis(3'-hydroxyphenyl)ethane (26) were the most active compounds regarding estradiol receptor affinity, exhibiting Ka values of 0.73 X 10(8) and 0.67 X 10(8) M-1, respectively. In vivo, 23 and 26 showed only very small uterotrophic activity in the mouse. They strongly inhibited (73%) the estrone-stimulated mouse uterine growth. Tested on the 9,10-dimethyl-1,2-benzanthracene induced hormone-dependent mammary adenocarcinoma of the Sprague-Dawley rat, compounds 23 and 26 exhibited a dose-dependent inhibition of the tumor growth, having a strong effect at a dose of 20 (mg/kg)/day (compound 23).

  DOI：

  10.1021/jm00182a006
• 作为产物：
  描述：

  3,4-二甲氧基苯甲酸甲酯 在 lithium aluminium tetrahydride 、 titanium(III) chloride 、 magnesium 作用下， 以 乙二醇二甲醚 为溶剂， 反应 18.5h， 生成 1,1'-(2,3-Dimethylbutane-2,3-diyl)bis(3,4-dimethoxybenzene)
  参考文献：
  名称：

  Antiestrogens. Synthesis and evaluation of mammary tumor inhibiting activity of 1,1,2,2-tetraalkyl-1,2-diphenylethanes

  摘要：

  Among the newly synthesized 1,1,2,2-tetraalkyl-1,2-diphenylethanes, 1,1,2,2-tetramethyl-1,2-bis(4'-hydroxyphenyl)ethane (23) and 1,1,2,2-tetramethyl-1,2-bis(3'-hydroxyphenyl)ethane (26) were the most active compounds regarding estradiol receptor affinity, exhibiting Ka values of 0.73 X 10(8) and 0.67 X 10(8) M-1, respectively. In vivo, 23 and 26 showed only very small uterotrophic activity in the mouse. They strongly inhibited (73%) the estrone-stimulated mouse uterine growth. Tested on the 9,10-dimethyl-1,2-benzanthracene induced hormone-dependent mammary adenocarcinoma of the Sprague-Dawley rat, compounds 23 and 26 exhibited a dose-dependent inhibition of the tumor growth, having a strong effect at a dose of 20 (mg/kg)/day (compound 23).

  DOI：

  10.1021/jm00182a006

文献信息

• The effect of diphenylethane side-chain substituents on dibenzocyclohexadiene formation and their inhibition of α-synuclein aggregation in vitro
  作者：Gabriel Bernardes、Omer Munir、Ed S. Krol

  DOI：10.1016/j.bmc.2022.117147

  日期：2023.1

  activity. To test this hypothesis we prepared a series of 1,2-bis-ethane di-catechols with 0, 2 and 4 methyl substituents on the linker. We have confirmed that these compounds undergo intramolecular cyclization to form dibenzocyclohexadienes and that steric interactions between the methyl substituents leads to an increase in the rate of intramolecular cyclization, which is in contrast to what was observed

  天然存在的二儿茶酚木酚素去甲二氢愈创木酸 (NDGA) 和丁基接头上没有甲基的类似物均在 pH 7.4 下发生分子内环化，形成二苯并环辛二烯。NDGA 和这些二苯并环辛二烯已被证明可以防止α-突触核蛋白的体外聚集，α-突触核蛋白是一种与帕金森病相关的本质上无序的蛋白质。NDGA 在丁基接头上有两个邻位甲基，这些甲基的存在减弱了分子内环化与未取代类似物的速率，这与预期的 Thorpe-Ingold 效应相反，这可能是由于环化过程中的空间排斥。 已知许多 1,2-双乙烷二邻苯二酚可在体外抑制 α-突触核蛋白聚集我们假设这些化合物经历了类似的分子内环化，环化产物可能是该活性的原因。为了检验这一假设，我们制备了一系列 1,2-双乙烷二邻苯二酚，在接头上具有 0、2 和 4 个甲基取代基。我们已经证实这些化合物经过分子内环化形成二苯并环己二烯，甲基取代基之间的空间相互作用导致分子内环化速率增加，这与
• Hammett Analysis of Photodecarbonylation in Crystalline 1,3-Diarylacetones
  作者：Marino J. E. Resendiz、Miguel A. Garcia-Garibay

  DOI：10.1021/ol0480527

  日期：2005.2.1

  The relative quantum yields and chemical efficiencies of crystalline p,p'-disubstituted 1,3-diphenyl-2-propanones with 4-MeO2 4Me(2) 4-F-2 4-CF3, and 3,4-diMeO groups were determined by parallel irradiation of polycrystalline samples. Variations in quantum yields that span a factor of 4 are analyzed in terms of the effects of substituents on the stability of the benzylic radical. All solid-state reactions proceeded with 100% chemoselectivity and in >95% chemical yield.
• HARTMANN R. W.; KRANZFELDER G.; ANGERER E.; SCHOENEBERGER H., J. MED. CHEM., 1980, 23, NO 8, 841-848
  作者：HARTMANN R. W.、 KRANZFELDER G.、 ANGERER E.、 SCHOENEBERGER H.

  DOI：——

  日期：——
• Antiestrogens. Synthesis and evaluation of mammary tumor inhibiting activity of 1,1,2,2-tetraalkyl-1,2-diphenylethanes
  作者：Rolf W. Hartmann、Gerhard Kranzfelder、Erwin Von Angerer、Helmut Schoenenberger

  DOI：10.1021/jm00182a006

  日期：1980.8

  Among the newly synthesized 1,1,2,2-tetraalkyl-1,2-diphenylethanes, 1,1,2,2-tetramethyl-1,2-bis(4'-hydroxyphenyl)ethane (23) and 1,1,2,2-tetramethyl-1,2-bis(3'-hydroxyphenyl)ethane (26) were the most active compounds regarding estradiol receptor affinity, exhibiting Ka values of 0.73 X 10(8) and 0.67 X 10(8) M-1, respectively. In vivo, 23 and 26 showed only very small uterotrophic activity in the mouse. They strongly inhibited (73%) the estrone-stimulated mouse uterine growth. Tested on the 9,10-dimethyl-1,2-benzanthracene induced hormone-dependent mammary adenocarcinoma of the Sprague-Dawley rat, compounds 23 and 26 exhibited a dose-dependent inhibition of the tumor growth, having a strong effect at a dose of 20 (mg/kg)/day (compound 23).