2,2-difluoro-1-(naphthalen-2-yl)-2-(phenylsulfonyl)ethanol | 871504-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2-difluoro-1-(naphthalen-2-yl)-2-(phenylsulfonyl)ethanol
• 英文别名: 2,2-difluoro-1-(naphthalen-2-yl)-2-(phenylsulfonyl)ethan-1-ol；alpha-(Phenylsulfonyldifluoromethyl)naphthalene-2-methanol；2-(benzenesulfonyl)-2,2-difluoro-1-naphthalen-2-ylethanol
• CAS: 871504-64-2
• 化学式: C₁₈H₁₄F₂O₃S
• 分子量: 348.37
• InChiKey: YFGZJTCUAFGBIF-UHFFFAOYSA-N

物化性质

• 沸点：
  564.5±50.0 °C(Predicted)
• 密度：
  1.383±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-1-(naphthalen-2-yl)-2-(phenylsulfonyl)ethanol 在 吡啶 、 五氯化磷 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以81%的产率得到2-(1-chloro-2,2-difluoro-2-(phenylsulfonyl)ethyl)naphthalene
  参考文献：
  名称：

  通过α-（苯基磺酰基）二氟甲基化苯甲酸酯的脱氢磺酰化反应制备1-芳基-2,2-二氟烯醇酯

  摘要：

  由α-（苯磺酰基）-二氟甲基化的苯甲酸酯3制备了1-芳基-2,2-二氟烯醇苯甲酸酯4，可以通过简单的醛与PhSO 2 CF 2 H（或TMSCF 2 SO 2 Ph ）。2，2-二氟烯醇酯4是比2，2-二氟烯醇硅醚相对更稳定的化合物，它们有望作为有趣的氟化结构单元进行进一步的修饰。

  DOI：

  10.1016/j.jfluchem.2007.03.004
• 作为产物：
  描述：

  ethyl 2,2-difluoro-2-(phenylthio)acetate 在 chromium(VI) oxide 、 potassium hydroxide 作用下， 以 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2,2-difluoro-1-(naphthalen-2-yl)-2-(phenylsulfonyl)ethanol
  参考文献：
  名称：

  用PhSO 2 CF 2 COOK对醛进行脱羧二氟甲基化：轻松有效地获得二氟甲基化甲醇

  摘要：

  在无金属和无配体条件下，开发了PhSO 2 CF 2 COOK与醛类的新型脱羧二氟甲基化反应。该反应非常温和，并且可以耐受多种醛类（可烯醇化和不可烯醇化的醛），为合成结构多样的二氟甲基化甲醇提供了简便而有效的方法，产率中等至优异。

  DOI：

  10.1016/j.tetlet.2018.07.021

文献信息

• Nucleophilic (Phenylsulfonyl/arylthio)difluoromethylation of Aldehydes with TMSCF₂Br: A Three-Component Strategy
  作者：Qiqiang Xie、Ziyue Zhu、Chuanfa Ni、Jinbo Hu

  DOI：10.1021/acs.orglett.9b03520

  日期：2019.11.15

  (phenylsulfonyl/arylthio)difluoromethylation of aldehydes with TMSCF2Br was developed. The reaction proceeds through in situ generation of difluorocarbene, which is captured by PhSO2Na or ArSNa to form the corresponding PhSO2CF2- or PhSCF2- anions, followed by nucleophilic addition to aldehydes to give the desired difluoromethylated products.

  建立了一种用TMSCF2Br进行醛类亲核（苯磺酰基/芳硫基）二氟甲基化的有效方法。该反应通过原位产生二氟卡宾而进行，该二氟卡宾被PhSO 2 Na或ArSNa捕获以形成相应的PhSO 2 CF 2-或PhSCF 2-阴离子，然后亲核加成至醛中以得到所需的二氟甲基化产物。
• Facile preparation of difluoromethyl- and monofluoromethyl-containing amides via Ritter reaction
  作者：Jun Liu、Chuanfa Ni、Ya Li、Laijun Zhang、Guanyu Wang、Jinbo Hu

  DOI：10.1016/j.tetlet.2006.07.079

  日期：2006.9

  difluoromethylated acetamides in good yields, which is remarkably more efficient than the previously reported Ritter reactions with corresponding trifluoromethylated carbinols. Similarly, monofluoromethylated and (benzenesulfonyl)difluoromethylated carbinols have shown good reactivity in the Ritter reactions. Since the acetamides can be mildly deacetylated to give amines, the present methodology provides a convenient

  发现仲和叔二氟甲基化甲醇在浓硫酸的催化下容易与乙腈反应，以良好的收率得到相应的二氟甲基化乙酰胺，这比先前报道的与相应的三氟甲基化甲醇的Ritter反应明显更有效。类似地，单氟甲基化的和（苯磺酰基）二氟甲基化的甲醇在Ritter反应中显示出良好的反应性。由于乙酰胺可以被轻度地脱乙酰基而得到胺，因此本方法学为从简单的羰基化合物开始同时合成含二氟甲基和单氟甲基的胺提供了一种方便的方法。
• Efficient nucleophilic difluoromethylation of aldehydes with (phenylsulfonyl)difluoromethylzinc and (phenylsulfonyl)difluoromethylcadmium reagents
  作者：Fanzhou Jiang、Chuanfa Ni、Jinbo Hu

  DOI：10.1016/j.jfluchem.2016.12.005

  日期：2017.6

  strategy for nucleophilic addition to aldehydes with difluoromethyl organometallic reagents has been developed by functionalizing the difluoromethyl moiety with the phenylsulfonyl group (SO2Ph). This electron-withdrawing group influences both the thermodynamic stability and the nucleophilicity of difluoromethyl organometallic reagents, which plays an important role in the nucleophilic difluoromethylation

  通过用苯磺酰基（SO 2 Ph）官能化二氟甲基部分，已经开发了一种用二氟甲基有机金属试剂亲核加成醛的新策略。该吸电子基团影响二氟甲基有机金属试剂的热力学稳定性和亲核性，这在醛的亲核二氟甲基化中起重要作用。
• Nucleophilic difluoromethylation of carbonyl compounds using TMSCF2SO2Ph and Mg0-mediated desulfonylation
  作者：Chuanfa Ni、Jinbo Hu

  DOI：10.1016/j.tetlet.2005.09.162

  日期：2005.11

  A new nucleophilic difluoromethylation chemistry using fluoride-induced (phenylsulfonyl)difluoromethylation with TMSCF2SO2Ph followed by the magnesium-metal-mediated desulfonylation has been achieved. This methodology is compatible with both enolizable and non-enolizable aldehydes and ketones and has special advantage in the case of enolizable aldehydes. The new efficient desulfonylation method is considered to be environmentally benign due to the absence of mercury. (c) 2005 Elsevier Ltd. All rights reserved.
• Nucleophilic difluoro(phenylsulfonyl)methylation of carbonyls with PhSO2CF2H reagent in the presence of in situ generated substoichiometric amount of base
  作者：Mingyou Hu、Bing Gao、Chuanfa Ni、Laijun Zhang、Jinbo Hu

  DOI：10.1016/j.jfluchem.2013.05.015

  日期：2013.11

  The reactions between carbonyl compounds and PhSO2CF2H using substoichiometric amount of base in situ generated from N(TMS)(3) and catalytic amount of Me4NF have been investigated. It is found that both enolizable and non-enolizable aldehydes are suitable substrates to undergo nucleophilic difluoro(phenylsulfonyl)methylation. Compared to the previously reported trifluoromethylation of carbonyls with CF3H under the similar reaction conditions, the unique reactivity of PhSO2CF2H is attributed to its higher acidity than CF3H and the reversibility of its addition reaction with ketones under basic conditions. (C) 2013 Elsevier B.V. All rights reserved.