meso-3,4-dimethyl-3,4 bis(4'-methoxyphenyl)hexane | 74385-20-9

• 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: meso-3,4-dimethyl-3,4 bis(4'-methoxyphenyl)hexane
• 英文别名: 1-Methoxy-4-[4-(4-methoxyphenyl)-3,4-dimethylhexan-3-yl]benzene
• CAS: 74385-20-9
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: NSNRHLRENBSPHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  24
• 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：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  meso-3,4-dimethyl-3,4 bis(4'-methoxyphenyl)hexane 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到4-[4-(4-Hydroxyphenyl)-3,4-dimethylhexan-3-yl]phenol
  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：

  3,4-二甲基-3,4-二苯基己烷 在 palladium on activated charcoal 亚硝酸特丁酯 、 三氟化硼乙醚 、 氢气 、 硝酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸酐 、 乙酸乙酯 为溶剂， 生成 meso-3,4-dimethyl-3,4 bis(4'-methoxyphenyl)hexane
  参考文献：
  名称：

  Photochemically generated ion and radical pairs. Self-destructive charge-transfer complexes

  摘要：

  Irradiation of CT complexes between 4-methoxy-4'-X-bicumenes, 1a-e (X = H, a; OMe, b; Me, c, CF3, d, CN, e) and tetranitromethane (2) results in efficient generation of radical and ion pairs (phi-almost-equal-to 0.20). The identity of the final products depends on the dynamics of these pairs, which in turn is dramatically influenced by substitution and solvent. In all cases, 2.- dissociates rapidly ( < 3 ps) into (NO2)C-3(-) (4-) and NO2.. In CH2Cl2, 1a.+ reacts with 4- (aromatic trinitromethylation) and undergoes C-C bond fragmentation before diffusional separation of fragments can occur. Thus, a tetrad of reactive intermediates (cumyl radical, NO2., p-methoxycumyl cation and 4-) are produced in a single solvent cage. The cumyl radical is oxidized by 2, and both cumyl cations undergo alpha-trinitromethylation. The cumyl cations undergo trinitromethylation in the original solvent cage which is kinetically equivalent to a contact ion pair (CIP). In CH3CN the fragmentation is accompanied by aromatic nitration (radical collapse). In this solvent, the p-methoxycumyl cations produced by cleavage reaction undergo trinitromethylation at the CIP stage, but cumyl cations produced by thermal oxidation of the cumyl radicals are trapped by 4- at the solvent-separated ion pair stage. In CH2Cl2, 1b-c.+ undergo exclusively fragmentation, completely within the solvent cage. The cleavage of 1d-e.+ is much slower, and the radical cations undergo instead aromatic trinitromethylations. The observed substituent effect on the rate of cleavage (p+ = -2.2) indicates significant charge transfer across the scissile bond in the transition state for this process. The products of these reactions are predominantly derived from ion annihilation. The radical coupling processes are limited to radical cation/radical collapse that lead to nitrated products.

  DOI：

  10.1021/jo00313a021

文献信息

• Dicyanobenzene sensitized carbon-carbon bond cleavage in methoxybicumenes. Products and mechanistic studies
  作者：Przemyslaw Maslak、William H. Chapman

  DOI：10.1016/s0040-4020(01)88366-6

  日期：1990.1

  Radical cations of p-methoxy-p-X-bicumenes generated by ET to excited-state dicyanobenzene undergo rapid irreversible C-C bond scission giving cumyl cations and radicals. The photoefficiency of the process (Φ = 0.13 for X = MeO, Φ< 0.005 for X = CN) and the fate of the radicals produced depends strongly on substitution.

  由ET生成的对甲氧基-pX-双碳二烯的自由基阳离子到激发态的二氰基苯经历快速不可逆的CC键断裂，产生枯基阳离子和自由基。该过程的光效率（对于X = MeO，Φ= 0.13；对于对于X = CN，Φ<0.005）和产生的自由基的命运在很大程度上取决于取代。
• Mesolytic Scission of C−C Bonds as a Probe for Photoinduced Electron Transfer Reactions of Quinones
  作者：Przemyslaw Maslak、William H. Chapman

  DOI：10.1021/jo952102r

  日期：1996.1.1

  Photoinduced electron transfer reactions of chlorinated benzoquinones are investigated using bibenzylic donors that undergo rapid fragmentation upon oxidation. The fragmentation rates and the quantum yields are used to probe the dynamics of back-electron transfer (BET) in two types of radical ion pairs. The triplet ion pairs formed by interception of excited state quinones give products with high quantum

  使用联苄供体，研究了氯化苯醌的光诱导电子转移反应，该供体在氧化时会发生快速断裂。碎片率和量子产率用于探测两种类型的自由基离子对中背电子转移（BET）的动力学。通过拦截激发态醌形成的三重态离子对可提供具有高量子产率的产物。由醌和供体之间的电荷转移（CT）配合物辐照形成的单线态离子对进行反应的效率明显降低。与CT辐射相比，第一种方法（三重态猝灭）的优势取决于BET的能量。对于BET相对较小DeltaG（et）的反应，此值较大；对于负DeltaG（bet）较高的反应，此值减小。
• Direct comparison of photoefficiencies of C–C bond scission in radical cations generated by photosensitized electron transfer and by irradiation of charge-transfer complexes
  作者：Przemyslaw Maslak、William H. Chapman

  DOI：10.1039/c39890001809

  日期：——

  Quantum yields for C–C bond scission are at least 50 times larger in radical cations of methoxybicumenes (1˙+) generated by quenching of the p-tetrachlorobenzoquinone (TCBQ) excited state (a process that results in triplet solvent-separated ion pairs) than in those obtained by the irradiation of [TCBQ ⋯(1)] charge-transfer complexes (a reaction that yields singlet contact ion pairs).

  的量子产率的C-C键断裂是在methoxybicumenes的自由基阳离子（至少大50倍1 ˙ +由淬火产生的）p -tetrachlorobenzoquinone（TCBQ）激发态（一个进程的结果在三重溶剂分离的离子对）与通过[TCBQ⋯（1）]辐照得到的电荷转移络合物相比（一种产生单线态接触离子对的反应）。
• 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：——
• MASLAK, PRZEMYSLAW;CHAPMAN, WILLIAM H. (JR), TETRAHEDRON, 46,(1990) N, C. 2715-2724
  作者：MASLAK, PRZEMYSLAW、CHAPMAN, WILLIAM H. (JR)

  DOI：——

  日期：——