1,1-difluoro-4-phenyl-2-butanol | 145299-87-2

• 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: 1,1-difluoro-4-phenyl-2-butanol
• 英文别名: 1,1-difluoro-4-phenylbutan-2-ol
• CAS: 145299-87-2
• 化学式: C₁₀H₁₂F₂O
• 分子量: 186.201
• InChiKey: MXIFGPYCPAUIIP-UHFFFAOYSA-N

物化性质

• 沸点：
  280.6±40.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1,1-difluoro-4-phenyl-2-butanol 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 (R)-1,1-Difluoro-4-phenyl-butan-2-ol
  参考文献：
  名称：

  A microbially-based approach for the synthesis of chiral secondary alcohols bearing the difluoromethyl or chlorodifluoromethyl group

  摘要：

  A synthetic approach to both enantiomers of the secondary alcohols [Ph(CH2)n CH(OH)CXF2 (n = 0-2) C6H13(CH2)n CH(OH)CFX2 (n = 0 or 2) and CXF2CH(OH)CH2CO2Et [X = H or Cl], involving the stereoselective hydrolysis of ester derivatives, is described. The absolute configurations of these difluoromethylated or chlorodifluoromethylated molecules were determined.

  DOI：

  10.1016/s0022-1139(00)81174-4
• 作为产物：
  描述：

  1,1-difluoro-4-phenylbutan-2-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以66%的产率得到1,1-difluoro-4-phenyl-2-butanol
  参考文献：
  名称：

  A microbially-based approach for the synthesis of chiral secondary alcohols bearing the difluoromethyl or chlorodifluoromethyl group

  摘要：

  A synthetic approach to both enantiomers of the secondary alcohols [Ph(CH2)n CH(OH)CXF2 (n = 0-2) C6H13(CH2)n CH(OH)CFX2 (n = 0 or 2) and CXF2CH(OH)CH2CO2Et [X = H or Cl], involving the stereoselective hydrolysis of ester derivatives, is described. The absolute configurations of these difluoromethylated or chlorodifluoromethylated molecules were determined.

  DOI：

  10.1016/s0022-1139(00)81174-4

文献信息

• Efficient and Direct Nucleophilic Difluoromethylation of Carbonyl Compounds and Imines with Me₃SiCF₂H at Ambient or Low Temperature
  作者：Yanchuan Zhao、Weizhou Huang、Ji Zheng、Jinbo Hu

  DOI：10.1021/ol202208b

  日期：2011.10.7

  by using a proper Lewis base activator, Me3SiCF2H can efficiently difluoromethylate various aldehydes, ketones, and imines to give the corresponding products in good to excellent yields at room temperature or even at −78 °C.

  自1995年以来，Me 3 SiCF 2 H被广泛认为是一种无效的二氟甲基化剂，它需要苛刻的反应条件才能裂解其相当惰性的Si–CF 2 H键。然而，现在发现，通过使用合适的路易斯碱活化剂，Me 3 SiCF 2 H可以有效地二氟甲基化各种醛，酮和亚胺，从而在室温或什至于-78的条件下以良好或优异的收率获得相应的产物。 ℃。
• Organocatalytic direct difluoromethylation of aldehydes and ketones with TMSCF₂H
  作者：Guang-Fen Du、Ying Wang、Cheng-Zhi Gu、Bin Dai、Lin He

  DOI：10.1039/c5ra04472c

  日期：——

  Organocatalytic direct difluoromethylation of aldehydes and ketones with TMSCF₂H.

  有机催化剂直接用TMSCF2H对醛和酮进行二氟甲基化。
• Convenient Synthesis of Difluoromethyl Alcohols from Both Enolizable and Non-Enolizable Carbonyl Compounds with Difluoromethyl Phenyl Sulfone
  作者：G. K. Surya Prakash、Jinbo Hu、Ying Wang、George A. Olah

  DOI：10.1002/ejoc.200500101

  日期：2005.6

  difluoromethylation of carbonyl compounds (both enolizable and non-enolizable aldehydes and ketones) has been achieved by using a nucleophilic (phenylsulfonyl)difluoromethylation-reductive desul-fonylation strategy. Difluoromethyl phenyl sulfone acts as a difluoromethyl anion ("CF2H-") equivalent. (C Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005).

  通过使用亲核（苯磺酰基）二氟甲基化-还原性脱磺酰化策略，已经实现了羰基化合物（可烯醇化和不可烯醇化的醛和酮）的通用和有效的亲核二氟甲基化。二氟甲基苯砜充当二氟甲基阴离子（“CF 2 H-”）等价物。(C Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)。
• Nucleophilic difluoromethylation and difluoromethylenation using bromodifluoromethyl phenyl sulfone
  作者：G.K. Surya Prakash、Ying Wang、Jinbo Hu、George A. Olah

  DOI：10.1016/j.jfluchem.2005.07.011

  日期：2005.10

  found to be an effective electron-transfer agent that promoted the reactions of bromodifluoromethyl phenyl sulfone with aldehydes to give structurally diverse (benzenesulfonyl)difluoromethylated alcohols in good yield, which can be further transformed into difluoromethyl alcohols and 1,1-difluoro-1-alkenes via reductive desulfonylation and Julia olefination, respectively.

  已发现四（二甲基氨基）乙烯（TDAE）是一种有效的电子转移剂，可促进溴二氟甲基苯基砜与醛的反应，从而以高收率获得结构多样的（苯磺酰基）二氟甲基化醇，可将其进一步转化为二氟甲基醇和1,1-二氟-1-烯烃分别通过还原性脱磺酰基反应和朱莉娅烯化反应。
• Nucleophilic difluoromethylation and difluoromethylenation of aldehydes and ketones using diethyl difluoromethylphosphonate
  作者：Petr Beier、Anastasia V. Alexandrova、Mikhail Zibinsky、G.K. Surya Prakash

  DOI：10.1016/j.tet.2008.10.006

  日期：2008.12

  New methodology for difluoromethylation and difluoromethylenation of aldehydes and ketones based on nucleophilic fluorination using diethyl difluoromethylphosphonate (1) was developed.

  开发了基于使用二氟甲基膦酸二乙酯 (1) 进行亲核氟化的醛和酮的二氟甲基化和二氟甲基化的新方法。