(2,4-Dichlorophenyl)(4-methoxyphenyl)methanol | 29334-25-6

• 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: (2,4-Dichlorophenyl)(4-methoxyphenyl)methanol
• 英文别名: (2,4-dichlorophenyl)-(4-methoxyphenyl)methanol
• CAS: 29334-25-6
• 化学式: C₁₄H₁₂Cl₂O₂
• 分子量: 283.154
• InChiKey: FFGLSHWBBKCCQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  419.6±45.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2,4-Dichlorophenyl)(4-methoxyphenyl)methanol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 2,4-Dichloro-1-[chloro-(4-methoxyphenyl)methyl]benzene
  参考文献：
  名称：

  Discovery of benzhydrylpiperazine derivatives as CB1 receptor inverse agonists via privileged structure-based approach

  摘要：

  The present study describes the identification via privileged structure-based approach of the benzhydrylpiperazine moiety as a potential scaffold to develop novel CB1 receptor modulators. Efficient structural optimization of the initial four hit compounds led to a high quality lead series, represented by compound 6c. Compound 6c is a highly potent and selective CB1 receptor inverse agonist that is able to reduce body weight in diet-induced obese Sprague-Dawley rats. The preparation of privileged structure-based library, the progression from hit to lead, the structure-activity relationships in the lead series and in vitro and in vivo activity of compound 6c are discussed. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.018
• 作为产物：
  描述：

  2,4-二氯苯甲酰氯 在 sodium tetrahydroborate 、 三氯化铝 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2,4-Dichlorophenyl)(4-methoxyphenyl)methanol
  参考文献：
  名称：

  聚合物支持的(2,6-二氯-4-烷氧基苯基)(2,4-二氯苯基)甲醇：用于固相有机合成的新连接体。

  摘要：

  开发了一种酸碱稳定的羟基四氯二苯甲基 (HTPM) 连接体，用于聚合物支持的有机合成。这里报道的连接体用于负载羧酸、胺、醇和酚，并且对布朗斯台德酸和路易斯酸、布朗斯台德碱和多种亲核试剂稳定。然而，HTPM 连接子可以通过 20% TFA 的溶剂分解置换反应方便地裂解。 【结构：见正文】

  DOI：

  10.1021/ol070150f

文献信息

• Dirhodium‐Catalyzed Enantioselective B−H Bond Insertion of <i>gem</i> ‐Diaryl Carbenes: Efficient Access to <i>gem</i> ‐Diarylmethine Boranes
  作者：Yu‐Tao Zhao、Yu‐Xuan Su、Xiao‐Yu Li、Liang‐Liang Yang、Ming‐Yao Huang、Shou‐Fei Zhu

  DOI：10.1002/anie.202109447

  日期：2021.11.2

  We report highly enantioselective dirhodium-catalyzed B−H bond insertion reactions with diaryl diazomethanes as carbene precursors. These reactions afforded chiral gem-diarylmethine borane compounds in high yield (up to 99 % yield), high activity (turnover numbers up to 14 300), high enantioselectivity (up to 99 % ee) and showed unprecedented broad functional group tolerance.

  我们报告了以二芳基重氮甲烷作为卡宾前体的高对映选择性二铑催化的 B-H 键插入反应。这些反应以高产率（高达 99 % 的产率）、高活性（高达 14 300 的转化率）、高对映选择性（高达 99 % ee）提供了手性 gem-二芳基次甲基硼烷化合物，并显示出前所未有的广泛官能团耐受性。
• Acid- and Base-Stable Esters: A New Protecting Group for Carboxylic Acids
  作者：Michio Kurosu、Kallolmay Biswas、Prabagaran Narayanasamy、Dean Crick

  DOI：10.1055/s-2007-983801

  日期：2007.8

  An acid- and base-stable protecting group for carboxylic acids is described. The esters of (2,6-dichloro-4-methoxyphenyl)(2,4-dichlorophenyl)methanol are stable to Bronsted and Lewis acids, Bronsted bases, and a wide variety of nucleophiles; however, the esters can be conveniently deprotected by a solvolytic displacement reaction with 20% trifluoroacetic acid.

  描述了一种酸和碱稳定的羧酸保护基团。(2,6-二氯-4-甲氧基苯基)(2,4-二氯苯基)甲醇的酯对布朗斯台德和路易斯酸、布朗斯台德碱和多种亲核试剂稳定；然而，可以通过与 20% 三氟乙酸的溶剂分解置换反应方便地对酯进行脱保护。
• Polymer-Supported (2,6-Dichloro- 4-alkoxyphenyl)(2,4-dichlorophenyl)methanol:  A New Linker for Solid-Phase Organic Synthesis
  作者：Michio Kurosu、Kallolmay Biswas、Dean C. Crick

  DOI：10.1021/ol070150f

  日期：2007.3.1

  amines, alcohols, and phenols, and are stable to Bronsted and Lewis acids, Bronsted bases, and a wide variety of nucleophiles. However, the HTPM linkers can conveniently be cleaved by the solvolytic displacement reactions with 20% TFA. [structure: see text]

  开发了一种酸碱稳定的羟基四氯二苯甲基 (HTPM) 连接体，用于聚合物支持的有机合成。这里报道的连接体用于负载羧酸、胺、醇和酚，并且对布朗斯台德酸和路易斯酸、布朗斯台德碱和多种亲核试剂稳定。然而，HTPM 连接子可以通过 20% TFA 的溶剂分解置换反应方便地裂解。 【结构：见正文】
• Discovery of benzhydrylpiperazine derivatives as CB1 receptor inverse agonists via privileged structure-based approach
  作者：Tao Meng、Jue Wang、Hongli Peng、Guanghua Fang、Min Li、Bing Xiong、Xin Xie、Yongliang Zhang、Xin Wang、Jingkang Shen

  DOI：10.1016/j.ejmech.2009.12.018

  日期：2010.3

  The present study describes the identification via privileged structure-based approach of the benzhydrylpiperazine moiety as a potential scaffold to develop novel CB1 receptor modulators. Efficient structural optimization of the initial four hit compounds led to a high quality lead series, represented by compound 6c. Compound 6c is a highly potent and selective CB1 receptor inverse agonist that is able to reduce body weight in diet-induced obese Sprague-Dawley rats. The preparation of privileged structure-based library, the progression from hit to lead, the structure-activity relationships in the lead series and in vitro and in vivo activity of compound 6c are discussed. (C) 2009 Elsevier Masson SAS. All rights reserved.