1-(p-bromophenyl)-2,2-difluorobut-3-en-1-ol | 189949-30-2

• 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-(p-bromophenyl)-2,2-difluorobut-3-en-1-ol
• 英文别名: 1-(4-Bromophenyl)-2,2-difluoro-3-butene-1-ol；1-(4-bromophenyl)-2,2-difluorobut-3-en-1-ol
• CAS: 189949-30-2
• 化学式: C₁₀H₉BrF₂O
• 分子量: 263.082
• InChiKey: CSRGFRGPUSJYEB-UHFFFAOYSA-N

物化性质

• 沸点：
  338.5±42.0 °C(Predicted)
• 密度：
  1.496±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(p-bromophenyl)-2,2-difluorobut-3-en-1-ol 在 4-二甲氨基吡啶 、 pseudomonas fluorescens lipase 、 N,N'-二环己基碳二亚胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (+)-[(R)-1-(p-bromophenyl)-2,2-difluorobut-3-enyl] (S)-acetoxy(phenyl)acetate
  参考文献：
  名称：

  Synthesis of optically active 2,2-difluorohomoallylalcohols by lipase-catalyzed transesterification

  摘要：

  Racemic 2,2-difluorohotnoallylalcohols could be resolved into (R)-alcohols and (S)-acetates through Pseudomonas fluorescens lipase-catalyzed enantioselective transesterification. The utility of the resulting chiral, non-racemic 2,2-difluorohomoallylalcohols was demonstrated by conversion of one of the (S)-acetates into a synthetically important 2,2-difluoro-3-hydroxycarboxylate derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00612-2
• 作为产物：
  描述：

  3-溴-3,3-二氟丙烯 、 对溴苯甲醛 在 indium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(p-bromophenyl)-2,2-difluorobut-3-en-1-ol
  参考文献：
  名称：

  Rh(III)-催化氧化还原中性苯甲酰胺 C-H 烯基化与偕二氟高烯丙基甲硅烷基醚通过 β-H 消除

  摘要：

  含氟分子广泛应用于医药和农化行业。在此我们报告了 2-(3,3-difluoro-4-(silyloxy)but-1-en-1-yl)benzamides 的合成，从前所未有的铑 (III) 催化的各种苯甲酰胺与二氟高烯丙基甲硅烷基醚的烯基化反应。该协议的实用性体现在其广泛的底物兼容性、良好的官能团耐受性、易于扩展和高区域选择性。二氟高烯丙基甲硅烷基醚中的氧使 β-H 消除成为可能，从而抑制 β-F 消除和苯甲酰胺的二烯基化。这种氧化还原中性反应通过以下方式有效进行N-O键在没有外部氧化剂的情况下断裂，因此为从现成的氟化合成子中合成精细的二氟化化合物提供了新的机会。

  DOI：

  10.1039/d3cc00529a

文献信息

• Copper-free defluorinative alkylation of allylic difluorides through Lewis acid-mediated C–F bond activation
  作者：Hikaru Yanai、Haruna Okada、Azusa Sato、Midori Okada、Takeo Taguchi

  DOI：10.1016/j.tetlet.2011.03.148

  日期：2011.6

  The reactions of difluorohomoallyl alcohols with trialkylaluminiums smoothly proceeded in CH2Cl2 at room temperature to give (Z)-fluoro-olefin products in excellent yields. On the basis of this chemistry, fluoro-olefinic dipeptide isostere of norvalinyl glycine was synthesized in stereoselective manner. (C) 2011 Elsevier Ltd. All rights reserved.
• Indium-Mediated Reaction of 3-Bromo-3,3-difluoropropene and Bromodifluoromethylacetylene Derivatives with Aldehydes
  作者：Masayuki Kirihara、Tomofumi Takuwa、Shinobu Takizawa、Takefumi Momose、Hideo Nemoto

  DOI：10.1016/s0040-4020(00)00749-3

  日期：2000.10

  Aldehydes reacted with 3-bromo-3,3-difluoropropene at the a-position in the presence of indium to afford 1-substituted-2,2-difluorobut-3-en-1-ols. Ketones and other electrophiles are inert under the examined conditions. The reaction of bromodifluoromethyl-acetylene derivatives with an aldehyde in the presence of indium provided difluorohomopropargylic alcohols. These reactions efficiently proceeded in polar solvents (water, DMF) under mild conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.
• α,α-difluoroallyl carbanion: Indium-mediation in its facile coupling with aldehydes
  作者：Masayuki Kirihara、Tomofumi Takuwa、Shinobu Takizawa、Takefumi Momose

  DOI：10.1016/s0040-4039(97)00480-2

  日期：1997.4

  Indium-mediated coupling of aldehydes with 3-bromo-3,3-difluoropropene gives 1-substituted-2,2-difluorobut-3-en-1-ols in high yields at room temperature. The coupling takes place at the gem-difluorocarbon selectively. Ketones are inert under the conditions examined. (C) 1997 Elsevier Science Ltd.
• Synthesis of (Z)-fluoroallyl azides through aluminium-mediated defluorinative functionalization reactions
  作者：Azusa Sato、Hikaru Yanai、Daiki Suzuki、Midori Okada、Takeo Taguchi

  DOI：10.1016/j.tetlet.2014.12.128

  日期：2015.2

  The reaction of difluorohomoallyl alcohols with Me2AlCl in CH2Cl2 selectively gave (Z)-fluoroallyl chlorides via S(N)2' type defluorinative chlorination. These chlorides were easily converted to the corresponding (Z)-fluoroallyl azides by the sequential nucleophilic azidation reaction using NaN3. Direct defluorinative azidation of the difluorohomoallyl alcohols was also achieved by treating with Me3SiN3 in the presence of Al(Oi-Pr)(3). Fluoroallyl azides thus obtained successfully applied to the Huisgen. 1,3-dipolar cycloaddition chemistry. (C) 2014 Elsevier Ltd. All rights reserved.