1,2-di-4-methylphenylethanol | 54881-85-5

• 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: 1,2-di-4-methylphenylethanol
• 英文别名: 1,2-di-p-tolylethanol；α.β-di-p-tolyl-ethanol；α-Oxy-α.β-di-p-tolyl-aethan；α.β-Di-p-tolyl-aethylalkohol；1,2-Bis(4-methylphenyl)ethanol
• CAS: 54881-85-5
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: WJISHFPGYLTIPS-UHFFFAOYSA-N

物化性质

• 熔点：
  77 °C(Solv: hexane (110-54-3))
• 沸点：
  344.8±11.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-di-4-methylphenylethanol 在 吡啶 、 三氯氧磷 作用下， 反应 2.0h， 生成 4,4'-二甲基-反-二苯乙烯
  参考文献：
  名称：

  Mechanistic Criteria for Cation Radical Reactions: Aminium Salt-Catalyzed Cyclopropanation

  摘要：

  Mechanistic studies of the cyclopropanation of a series of trans-stilbenes by ethyl diazoacetate catalyzed by two different triarylaminium salts decisively confirm a cation radical mechanism and rule out a hypothetical electrophilic mechanism. The elucidation of key aspects of these cation radical mechanisms, including kinetic vs equilibrium control of ionization and chain vs catalytic mechanisms, has also been achieved for these systems. New mechanistic criteria for the positive identification of cation radical mechanisms are proposed.

  DOI：

  10.1021/ja00126a007
• 作为产物：
  描述：

  1-甲基-4-(2-苯基乙基)-苯 在 copper(II) perchlorate 高氯酸 、 peroxodisulfate ion 作用下， 以 水 、 乙腈 为溶剂， 反应 0.42h， 生成 1,2-di-4-methylphenylethanol
  参考文献：
  名称：

  Carbon-hydrogen vs. carbon-carbon bond cleavage of 1,2-diarylethane radical cations in acetonitrile-water

  摘要：

  DOI：

  10.1021/jo00183a023

文献信息

• Chemoselective control of hydrogenation among aromatic carbonyl and benzyl alcohol derivatives using Pd/C(en) catalyst
  作者：Kazuyuki Hattori、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/s0040-4020(01)00421-5

  日期：2001.6

  of aromatic ketones and aldehydes quite smoothly give the corresponding methylene compounds via the formation of the intermediary benzyl alcohols in the presence of Pd/C as a catalyst. Therefore, it is extremely difficult to isolate the intermediary benzyl alcohol selectively. This paper describes a mild and chemoselective hydrogenation method of an aromatic carbonyl compound to benzyl alcohol using

  芳族酮和醛的氢解通过在Pd / C作为催化剂存在下形成中间体苄醇而非常顺利地得到相应的亚甲基化合物。因此，极其难于选择性地分离中间体苄醇。本文介绍了使用10％Pd / C（en）催化剂对芳族羰基化合物进行温和的化学选择性加氢制苯甲醇的方法，并将其应用于在苄基位置上存在苄醇官能团的情况下，在苄基位置进行化学选择性脱乙酰氧基化反应。分子。
• Nickel-Catalyzed Cross-Coupling of Styrenyl Epoxides with Boronic Acids
  作者：Daniel K. Nielsen、Abigail G. Doyle

  DOI：10.1002/anie.201101191

  日期：2011.6.27

  Let's get multicatalytic! A Ni0 catalyst complexed with a biaryldialkyl monophosphine ligand facilitates CC bond formation between styrenyl epoxides and aryl boronic acids (see scheme). X‐ray analysis of a catalytically active nickel/ligand complex supports a redox pathway involving CO bond activation. A variety of α‐substituted alcohols were generated with good reaction efficiency by a multicatalytic

  让我们多催化！一种Ni 0催化剂络合与biaryldialkyl单膦配体功能有助于Ç  C键的苯乙烯环氧化物之间形成与芳基硼酸（参见方案）。催化活性镍/配体络合物的X射线分析支持涉及CO键活化的氧化还原途径。通过多催化序列，可以产生各种具有良好反应效率的α-取代醇。
• Photochemically induced coupling reaction of triarylstibines with olefins
  作者：Naoki Kakusawa、Takashi Tsuchiya、Jyoji Kurita

  DOI：10.1016/s0040-4039(98)02281-3

  日期：1998.12

  Photoreaction of triarylstibines with styrenes resulted in the formation of 2-aryl-1-phenylethanols accompanied by air oxidation. Formation of the products has been explained by the valence expansion of the oxygen-antimony-styrene complex to a five-valent intermediate, followed by reductive coupling.

  三芳基stibines与苯乙烯的光反应导致形成2-芳基-1-苯基乙醇，并伴有空气氧化。产物的形成已通过氧-锑-苯乙烯络合物价键膨胀为五价中间体，然后还原偶联来解释。
• Cobalt-catalysed [1,2]-Wittig rearrangement of ethers to secondary alcohols
  作者：Sandip Pattanaik、Anurag Kumar、Chidambaram Gunanathan

  DOI：10.1039/d2cc06937g

  日期：——

  Stable ethers are successfully transformed into secondary alcohols via C–O bond activation using a simple cobalt pincer catalyst. Mechanistic studies indicate the involvement of radical pairs, and their sequential recombination and the subsequent hydrolysis results in the formation of secondary alcohols.

  使用简单的钴钳形催化剂通过C-O 键活化成功将稳定的醚转化为仲醇。机理研究表明自由基对的参与，它们的顺序重组和随后的水解导致仲醇的形成。
• Tandem Deoxygenative Geminal Fluorosulfonimidation of 1,2-Diketones via Formal N–F Insertion Enabled by Dealkylation-Resistant Phosphoramidite
  作者：Sujin Bak、Yeri Son、Jun-Ho Choi、Won-jin Chung、Sunjoo Hwang、Ha Eun Kim

  DOI：10.1055/a-2005-4296

  日期：——

  Our group has recently developed an α-fluoroamine synthesis using dioxaphospholenes derived from various 1,2-diketones and the dealkylation-resistant phosphoramidite as carbene surrogates, enabling the formal insertion into the N–F bond of (PhSO2)2NF. This full account presents the scope and limitations in terms of the reactivity and the site selectivity; these were rationalized through computational analysis. In addition, the efforts to broaden the synthetic utility of the current process by incorporating other nitrogen nucleophiles and halogen electrophiles are described.

  摘要我们的研究小组最近开发了一种α-氟胺合成方法，使用从各种 1,2-二酮和抗脱烷基亚磷酰胺中提取的二氧磷烯作为碳烯替代物，使(PhSO2)2NF 的 N-F 键正式插入。本报告全面介绍了反应性和位点选择性方面的范围和局限性；这些都是通过计算分析合理化的。此外，还介绍了通过加入其他氮亲核物和卤素亲电物来扩大当前工艺合成效用的努力。