4,4'-(butane-1,3-diyl)bis(1-methoxybenzene) | 198905-19-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4,4'-(butane-1,3-diyl)bis(1-methoxybenzene)
• 英文别名: 1,3-bis-(4-methoxy-phenyl)-butane；1,3-Bis-(4-methoxy-phenyl)-butan；1-Methoxy-4-[4-(4-methoxyphenyl)butan-2-yl]benzene
• CAS: 198905-19-0
• 化学式: C₁₈H₂₂O₂
• 分子量: 270.371
• InChiKey: CSBARPRLNPHNFU-UHFFFAOYSA-N

物化性质

• 沸点：
  152-154 °C(Press: 1 Torr)
• 密度：
  1.0616 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  4,4'-(butane-1,3-diyl)bis(1-methoxybenzene) 在 氢氧化钾 作用下， 生成 1,3-bis-(4-hydroxy-phenyl)-butane
  参考文献：
  名称：

  Synthetic Estrogenic Compounds. I. Monosubstituted Derivatives of 1,3-Di-(p-hydroxyphenyl)-propane

  摘要：

  DOI：

  10.1021/ja01248a037
• 作为产物：
  描述：

  4-(4-甲氧基苯基)丁烷-2-醇 在 吡啶 、 [nickel(II)(pyridine)4(chloride)2] 、 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate 、 四丁基溴化铵 、 4,4'-二叔丁基-2,2'-二吡啶 、 magnesium chloride 、 锌 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 生成 4,4'-(butane-1,3-diyl)bis(1-methoxybenzene)
  参考文献：
  名称：

  Ni催化醇与芳基卤化物的正式交叉电子偶联

  摘要：

  未活化醇的直接偶联仍然是当前合成化学中的一个挑战。我们在此展示了一种建立在醇与芳基卤化物的原位卤化/还原偶联以形成 Csp 2 -Csp 3键的策略。2-氯-3-乙基苯并[ d ]恶唑-3-鎓盐 (CEBO) 和 TBAB 作为温和溴化试剂的组合能够在 CH 3 中在一到 5 分钟内将范围广泛的醇快速转化为其溴化物对应物CN 和 DMF，在化学还原剂存在下与 Ni 催化的交叉亲电偶联条件相容。本方法适用于无数结构复杂的醇的芳基化，而无需制备卤代烷。更重要的是，温和且动力学快速的溴化过程在对称二醇的溴化/芳基化和多元醇中较少的空间位阻羟基中显示出良好的选择性，从而为二醇和多元醇的选择性官能化提供了希望，而无需费力的保护/脱保护操作。这项工作的实用性在许多碳水化合物、药物化合物和天然醇的芳基化中也很明显。

  DOI：

  10.1021/acscatal.1c04239

文献信息

• Nickel-catalyzed anti-Markovnikov hydroarylation of alkenes
  作者：Julia Nguyen、Andrea Chong、Gojko Lalic

  DOI：10.1039/c8sc05445b

  日期：——

  We have developed a nickel-catalyzed hydroarylation of alkenes using aryl halides as coupling partners. Excellent anti-Markovnikov selectivity is achieved with aryl-substituted alkenes and enol ethers. We also show that hydroarylation occurs with alkyl substituted alkenes to yield linear products. Preliminary examination of the reaction mechanism suggests irreversible hydrometallation as the selectivity

  我们开发了一种镍催化的烯烃加氢芳基化方法，使用芳基卤化物作为偶联伙伴。使用芳基取代的烯烃和烯醇醚可实现出色的抗马可夫尼科夫选择性。我们还表明，烷基取代的烯烃发生加氢芳基化，产生线性产物。反应机理的初步研究表明不可逆的加氢金属化是加氢芳基化的选择性决定步骤。
• Photochemical and Thermal Behavior of Styrenes within Acidic and Nonacidic Zeolites. Radical Cation <i>versus</i> Carbocation Formation
  作者：Frances L. Cozens、Roumiana Bogdanova、Michèle Régimbald、Hermenegildo García、Vinente Martí、J. C. Scaiano

  DOI：10.1021/jp9708963

  日期：1997.8.1

  Laser flash photolysis of a series of substituted styrenes embedded within the cavities of the large pore zeolite NaY leads to the formation of the corresponding styrene radical cation. The reactivity and spectra of these radical cations embedded within NaY are examined and compared to the reactivity of the same radical cations in solution. It is found that for the highly reactive parent styrene radical cation the zeolite framework provides a strong stabilizing effect. For the 4-methoxy-substituted styrene radical cation the zeolite framework plays less of a role in stabilizing the radical cation as compared to the reactivity of the same radical cation in acetonitrile solution. Rigorous analysis of the thermal stability of 4-methoxystyrene, 4-methylstyrene, and anethole in the zeolite micropores was carried out using two sources of NaY zeolite (Aldrich and The PQ Corporation). It was found that the thermal stability was surprisingly dependent on the source of the NaY zeolite. 4-Methoxystyrene, 4-methylstyrene, and anethole were thermally stable in NaY (Aldrich) but rapidly dimerized in NaY (PQ) upon incorporation with dichloromethane. We observed the formation of the same type of dimers not only for 4-methoxystyrene but also for 4-methylstyrene and anethole. In addition, 4-methoxystyrene was incorporated into a series of different acid zeolites (HZSM-5, HMordenite, HBeta, and HY) varying in the shape and size of their micropores where rapid thermal protonation occurs. Dimerization of the thermally formed 4-methoxyphenethyl cation with a neutral molecule of 4-methoxystyrene took place within all the acid zeolites examined. The generation of this secondary 1,3-bis(4-methoxyphenyl)-1-butylium ion was clearly observed in the medium pore ZSM-5. This carbocation was found to be thermally unstable in the acidic environment provided by the four acidic zeolites and underwent a proton and hydride transfer to form the more stable allylic 1,3-bis(4-methoxyphenyl)buten-1-ylium cation. In the large round cavities of HY a competing cyclization reaction took place which led to the formation of the 3-methyl-5-methoxy-1,4-methoxyphenylindanyl cation.
• Rao, V. Jayathirtha; Prevost, Nicolette; Ramamurthy, Chemical Communications, 1997, # 22, p. 2209 - 2210
  作者：Rao, V. Jayathirtha、Prevost, Nicolette、Ramamurthy、Kojima, Masanobu、Johnston

  DOI：——

  日期：——
• Carbenium ions generated upon adsorption of 4-methoxystyrenes onto acid zeolites. A kinetic study
  作者：Vicente Fornés、Hermenegildo García、Vicente Martí、Lorenzo Fernández

  DOI：10.1016/s0040-4020(98)00109-4

  日期：1998.4

  Adsorption of vinylanisole and trans-(4-methoxyphenyl)-1-propene into HY, HB and HZSM-5 allows us to detect the corresponding substituted 1,3-bis(4-methoxyphenyl)-1-propylium (2), 1-(4-methoxyphenyl)-6-methoxy-1-indanylium (5) and 1,3-bis(4-methoxyphenyl)-2-propen-1-ylium (8) cations as reactive intermediates. The kinetics can be followed by conventional spectrophotometers. Cation 2 appears as the shorter lived species, decaying in hours for the HY sample and within days when embedded in HZSM-5 zeolite. Cyclic indanyl cation 5 shows a lifetime much longer than 2. A growth of 8 concomitantly with the decay of 2 has been also observed. This has been taken as a proof of a hydride transfer from neutral 1,3-bis(4-methoxyphenyl)-1-propenes (the corresponding acyclic dimers observed as products) as donors to cations 2 as accepters leading to 8. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides
  作者：Quan Lin、Guobin Ma、Hegui Gong

  DOI：10.1021/acscatal.1c04239

  日期：2021.11.19

  and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation

  未活化醇的直接偶联仍然是当前合成化学中的一个挑战。我们在此展示了一种建立在醇与芳基卤化物的原位卤化/还原偶联以形成 Csp 2 -Csp 3键的策略。2-氯-3-乙基苯并[ d ]恶唑-3-鎓盐 (CEBO) 和 TBAB 作为温和溴化试剂的组合能够在 CH 3 中在一到 5 分钟内将范围广泛的醇快速转化为其溴化物对应物CN 和 DMF，在化学还原剂存在下与 Ni 催化的交叉亲电偶联条件相容。本方法适用于无数结构复杂的醇的芳基化，而无需制备卤代烷。更重要的是，温和且动力学快速的溴化过程在对称二醇的溴化/芳基化和多元醇中较少的空间位阻羟基中显示出良好的选择性，从而为二醇和多元醇的选择性官能化提供了希望，而无需费力的保护/脱保护操作。这项工作的实用性在许多碳水化合物、药物化合物和天然醇的芳基化中也很明显。