1-[4-(4-chlorobenzyl)phenyl]ethan-1-one | 1026082-44-9

• 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: 1-[4-(4-chlorobenzyl)phenyl]ethan-1-one
• 英文别名: 1-[4-[(4-Chlorophenyl)methyl]phenyl]ethanone
• CAS: 1026082-44-9
• 化学式: C₁₅H₁₃ClO
• 分子量: 244.721
• InChiKey: AKNXGHBKWCYVBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[4-(4-chlorobenzyl)phenyl]ethan-1-one 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 3-[4-(3-trifluoro-methyl-phenyl)-1,2,3,6-tetrahydro-1-pyridyl]-1-[4-(4-chloro-benzyl)-phenyl]-1-propanol
  参考文献：
  名称：

  Novel 1,2,3,6-tetrahydropyridine derivatives with potent antihypoxic activity

  摘要：

  A number of 1,2,3,6-tetrahydropyridine derivatives 1a-u were synthesised. They were examined for their antihypoxic actions in mice and rats using various hypoxic tests (eg, hypobaric hypoxia, cytotoxic hypoxia, and asphyxic anoxia). Some of the compounds described displayed significant antihypoxic activity. The antihypoxic activity of the most effective compound (1q) is propably unrelated to the hypothermising action. The participation of adrenergic and serotoninergic receptors in this effect can also be excluded. However, the activity of this compound may be related to the inhibition of cellular Ca2+ movement.

  DOI：

  10.1016/0223-5234(94)90059-0
• 作为产物：
  描述：

  对氯甲苯 、 4-溴苯乙酮 在 乙二醇二甲醚溴化镍 、 4,4'-二甲氧基-2,2'-联吡啶 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 36.0h， 以73%的产率得到1-[4-(4-chlorobenzyl)phenyl]ethan-1-one
  参考文献：
  名称：

  镍催化可实现聚合成对电解，使苄基CH键直接芳基化

  摘要：

  收敛对电合成是有机合成中的一种节能方法。但是，由于难以匹配反应伙伴的先天氧化还原特性而受到限制。在这里，我们使用镍催化来交叉耦合电化学电池两个相对电极上产生的两个中间体，从而实现苄基CH键的直接芳基化。该方法产生了多种多样的二芳基甲烷，这是药物和材料化学中的重要结构图案。初步的机理研究表明，苄基C–H键的氧化，Ni催化的C–C偶联以及Ni中间体的还原是催化循环的关键元素。

  DOI：

  10.1039/d0sc01445a

文献信息

• A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents
  作者：Visannagari Ramakrishna、Morla Jhansi Rani、Nareddula Dastagiri Reddy

  DOI：10.1002/ejoc.201701241

  日期：2017.12.29

  A zwitterionic palladium(II) complex has been found to be an efficient catalyst for Suzuki–Miyaura cross‐coupling reactions of aryl and heteroaryl organoboron reagents with various heteroaryl chlorides, aryl‐ and heteroarylmethyl chlorides, and aryl acid chlorides in neat water.

  两性离子钯（II）络合物是在纯净水中使芳基和杂芳基有机硼试剂与各种杂芳基氯化物，芳基和杂芳基甲基氯化物以及芳基酰氯发生铃木–宫浦交叉偶联反应的有效催化剂。
• Threefold and chemoselective couplings of triarylbismuths with benzylic chlorides and iodides using palladium catalysis
  作者：Maddali L. N. Rao、Ritesh J. Dhanorkar

  DOI：10.1039/c3ra46672h

  日期：——

  This paper describes the palladium-catalyzed studies on threefold coupling of triarylbismuth reagents with benzylic chlorides and iodides. The optimized protocol conditions are operationally simple, delivering threefold coupling of a variety of triarylbismuths in combination with benzylic chlorides and iodides. The two optimized protocols allowed the synthesis of a diverse range of unsymmetrical diarylmethanes in an efficient manner. As part of this study, chemoselective transformation of benzylic chlorides and iodides was also achieved.

  本文描述了对三芳基铋试剂与苄基氯和碘进行三重偶联的钯催化研究。经过优化的实验条件操作简单，使得多种三芳基铋与苄基氯和碘的三重偶联得以实现。这两种优化的实验方案使得不对称二芳基甲烷的合成变得高效。在本研究的过程中，还实现了苄基氯和碘的化学选择性转化。
• Pd-catalyzed chemoselective threefold cross-coupling of triarylbismuths with benzylic bromides
  作者：Maddali L. N. Rao、Ritesh J. Dhanorkar

  DOI：10.1039/c3ra40413g

  日期：——

  for the chemoselective cross-coupling of functionalized benzylic bromides with triarylbismuth reagents. Under the established conditions, catalyzed by palladium in the presence of K3PO4 base in DMA at 90 °C for 1 h, the threefold arylations using triarylbismuth reagents proceeded smoothly with electronically diverse benzylic bromides. All the coupling reactions furnished the corresponding functionalized

  对于功能化的苄基溴化物与三芳基铋试剂的化学选择性交叉偶联，证​​明了一种有效的钯催化方案。在既定条件下，钯在DMA中在90°C下在DMA中存在K 3 PO 4碱的条件下催化1 h，使用三芳基铋试剂进行的三重芳基化反应可通过电子形式多样的苄基溴顺利进行。所有偶联反应均以高收率提供了相应的官能化二芳基甲烷。
• Novel 1,2,3,6-tetrahydropyridine derivatives with potent antihypoxic activity
  作者：T Gizur、B Kiss、K Harsányi、E Kárpáti、É Pálosi、A Gere、E Lapis、I Laszlovszky、S Szabó、L Szporny

  DOI：10.1016/0223-5234(94)90059-0

  日期：1994.1

  A number of 1,2,3,6-tetrahydropyridine derivatives 1a-u were synthesised. They were examined for their antihypoxic actions in mice and rats using various hypoxic tests (eg, hypobaric hypoxia, cytotoxic hypoxia, and asphyxic anoxia). Some of the compounds described displayed significant antihypoxic activity. The antihypoxic activity of the most effective compound (1q) is propably unrelated to the hypothermising action. The participation of adrenergic and serotoninergic receptors in this effect can also be excluded. However, the activity of this compound may be related to the inhibition of cellular Ca2+ movement.
• Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C–H bonds
  作者：Lei Zhang、Xile Hu

  DOI：10.1039/d0sc01445a

  日期：——

  intermediates generated at the two opposite electrodes of an electrochemical cell, achieving direct arylation of benzylic C–H bonds. This method yields a diverse set of diarylmethanes, which are important structural motifs in medicinal and materials chemistry. Preliminary mechanistic study suggests oxidation of a benzylic C–H bond, Ni-catalyzed C–C coupling, and reduction of a Ni intermediate as key elements of

  收敛对电合成是有机合成中的一种节能方法。但是，由于难以匹配反应伙伴的先天氧化还原特性而受到限制。在这里，我们使用镍催化来交叉耦合电化学电池两个相对电极上产生的两个中间体，从而实现苄基CH键的直接芳基化。该方法产生了多种多样的二芳基甲烷，这是药物和材料化学中的重要结构图案。初步的机理研究表明，苄基C–H键的氧化，Ni催化的C–C偶联以及Ni中间体的还原是催化循环的关键元素。