(2,6-dichlorophenyl)(phenyl)methanol | 22543-77-7

• 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: (2,6-dichlorophenyl)(phenyl)methanol
• 英文别名: 2,6-Dichloro-I+/--phenylbenzenemethanol；(2,6-dichlorophenyl)-phenylmethanol
• CAS: 22543-77-7
• 化学式: C₁₃H₁₀Cl₂O
• 分子量: 253.128
• InChiKey: QNAWVPKEGJUCNH-UHFFFAOYSA-N

物化性质

• 熔点：
  57 °C
• 沸点：
  369.2±37.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  (2,6-dichlorophenyl)(phenyl)methanol 在 氯化亚砜 作用下， 以 苯 为溶剂， 生成 1,3-Dichloro-2-[chloro(phenyl)methyl]benzene
  参考文献：
  名称：

  Structure–activity relationships of diphenylpiperazine N-type calcium channel inhibitors

  摘要：

  A novel series of compounds derived from the previously reported N-type calcium channel blocker NP118809 (1-(4-benzhydrylpiperazin-1-yl)-3,3-diphenylpropan-1-one) is described. Extensive SAR studies resulted in compounds with IC50 values in the range of 10-150 nM and selectivity over the L-type channels up to nearly 1200-fold. Orally administered compounds 5 and 21 exhibited both anti-allodynic and anti-hyperalgesic activity in the spinal nerve ligation model of neuropathic pain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.008
• 作为产物：
  描述：

  苯甲醛 、 1,3-二氯苯 在 sodium 、 二异丙胺 、 天然橡胶 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(2,6-dichlorophenyl)(phenyl)methanol
  参考文献：
  名称：

  连续流中的芳烃和杂芳烃的成膜作用

  摘要：

  报道了在Me 2 EtN中使用NaDA（二异丙基酰胺钠）连续流动的（杂）芳烃的首次碱化。此流程可将在批分解条件下分解的官能化芳烃和杂芳烃进行皂化。所得的磺化（杂）芳烃立即与各种亲电子试剂（例如酮，醛，异氰酸酯，烷基溴化物和二硫化物）反应，以高收率提供多官能化（杂）芳烃。无需进一步优化就可以扩大规模。

  DOI：

  10.1002/anie.201803961

文献信息

• Method of preparing organomagnesium compounds
  申请人：Ludwig-Maximilians-Universität München

  公开号：EP1582523A1

  公开（公告）日：2005-10-05

  The present invention is directed to a reagent for use in the preparation of organomagnesium compounds as well as to a method of preparing such organomagnesium compounds. The present invention furthermore provides a method of preparing functionalized or unfunctionalized organic compounds as well as the use of the reagents of the present invention in the preparation of organometallic compounds and their reaction with electrophiles. Finally, the present invention is directed to the use of lithium salts - LiY in the preparation of organometallic compounds and their reactions with electrophiles and to an organometallic compound which is obtainable by the disclosed method.

  本发明涉及一种试剂，用于制备有机镁化合物，以及一种制备这种有机镁化合物的方法。本发明还提供了一种制备官能化或非官能化有机化合物的方法，以及本发明的试剂在制备有机金属化合物及其与亲电试剂反应中的应用。最后，本发明涉及锂盐LiY在制备有机金属化合物及其与亲电试剂反应中的应用，以及通过所披露方法获得的有机金属化合物。
• Directed Magnesiation of Polyhaloaromatics using the Tetramethylpiperidylmagnesium Reagents TMP₂Mg⋅2 LiCl and TMPMgCl⋅LiCl
  作者：Andreas Unsinn、Christoph J. Rohbogner、Paul Knochel

  DOI：10.1002/adsc.201300185

  日期：2013.5.17

  A convenient and efficient functionalization of polyhaloaromatics via regioselective magnesiation has been developed. Starting from simple, inexpensive but structurally challenging arenes, metallation by magnesium amide bases was achieved under mild conditions. The desired Grignard reagents were stable towards aryne formation, were obtained in good yields within short reaction times and could be reacted

  已经开发了通过区域选择性放大作用方便且有效地官能化多卤代芳族化合物。从简单，便宜但具有结构挑战性的芳烃开始，在温和的条件下实现了酰胺化镁碱的金属化。所需的格氏试剂对芳烃的形成是稳定的，可以在短的反应时间内以高收率获得，并且可以与多种典型的亲电试剂反应，以诱人的收率提供优良的，功能化的结构单元。作为一种应用，我们制备了从新西兰艾蒿麦地那缘分离的抗微生物天然产物2,6-二氯-3-苯乙基苯酚。该合成涉及通过 苯硼酸频哪醇酯衍生物的金属化和随后的选择性交叉偶联。
• Process for producing benzhydrols
  申请人：K I CHEMICAL INDUSTRY CO., LTD.

  公开号：EP0801048A1

  公开（公告）日：1997-10-15

  There is disclosed a process for producing benzhydrls by reacting an arylmetal compound with an aromatic aldehyde. According to this process, benzhydrols useful as raw materials for medicines and photopolymerization initiators can be produced in a high yield and industrially advantageously.

  本发明揭示了一种通过将芳基金属化合物与芳香醛反应来生产苯甲醇的方法。根据这种方法，可高产率地、在工业上具有优势地生产用作药物原料和光聚合引发剂的苯甲醇。
• Synthesis, Stability, and Reactions of 2,6-Dichlorophenyllithium
  作者：Thomas H. Kress、M. Robert Leanna

  DOI：10.1055/s-1988-27714

  日期：——

  A convenient, general, and regioselective synthesis of 2,6-dichloroaromatic compounds from m-dichlorobenzene is described. The stability of 2,6-dichlorophenyllithium is examined.

  介绍了一种从间二氯苯合成 2,6-二氯芳香族化合物的简便、通用和区域选择性方法。研究了 2,6-二氯苯锂的稳定性。
• Continuous Flow Preparation of Benzylic Sodium Organometallics
  作者：Johannes H. Harenberg、Rajasekar Reddy Annapureddy、Konstantin Karaghiosoff、Paul Knochel

  DOI：10.1002/anie.202203807

  日期：2022.7.25

  A lateral sodiation of alkyl(hetero)arenes using on-demand generated (2-ethylhexyl)sodium in the presence of TMEDA is reported. Various electrophiles were used for trapping of the benzyl sodium species generated in continuous flow as well as in batch. The continuous flow metalation was scaled-up using an in-line quench. The method was used in the synthesis of several industrial relevant compounds.

  据报道，在 TMEDA 存在下，使用按需生成的 (2-乙基己基)钠对烷基（杂）芳烃进行横向钠化。使用各种亲电子试剂来捕获连续流动以及批量产生的苄基钠物质。使用在线淬火放大连续流金属化。该方法用于多种工业相关化合物的合成。