2,2-difluoro-1-phenyl-4-triisopropylsilylbut-3-yn-1-ol | 280561-94-6

• 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: 2,2-difluoro-1-phenyl-4-triisopropylsilylbut-3-yn-1-ol
• 英文别名: 1-(triisopropylsilyl)-3,3-difluoro-4-phenyl-1-butyn-4-ol；2,2-Difluoro-1-phenyl-4-tri(propan-2-yl)silylbut-3-yn-1-ol
• CAS: 280561-94-6
• 化学式: C₁₉H₂₈F₂OSi
• 分子量: 338.513
• InChiKey: QLOGGIJLVCZFLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  2,2-difluoro-1-phenyl-4-triisopropylsilylbut-3-yn-1-ol 在 Wilkinson's catalyst 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 33.0h， 生成 4,4-difluoro-3,7-diphenylisochroman
  参考文献：
  名称：

  Lanthanide Triflate-Catalyzed Preparation of β,β-Difluorohomopropargyl Alcohols in Aqueous Media. Application to the Synthesis of 4,4-Difluoroisochromans

  摘要：

  An indium-mediated Barbier-type reaction of difluoropropargyl bromide with several aldehydes in aqueous media was enhanced by a catalytic amount of a lanthanide triflate (5 mol %). The reaction gave the corresponding beta,beta-difluorohomopropargyl alcohols with high regioselectivity. The [2 + 2 + 2] alkyne cyclotrimerization of beta,beta-difluorohomopropargyl alcohols with monosubstituted acetylenes produced 4,4-difluoroisochromans in good yields with moderate regioselectivity.

  DOI：

  10.1021/jo0614588
• 作为产物：
  描述：

  lithium triisopropylsilyl acetylide 在 锌 作用下， 以 四氢呋喃 为溶剂， 生成 2,2-difluoro-1-phenyl-4-triisopropylsilylbut-3-yn-1-ol
  参考文献：
  名称：

  Expedient synthesis of α,α-difluorohomopropargylic alcohols from TIPS-difluorobromopropyne via a Zn-mediated propargylation of aldehydes and ketones

  摘要：

  The synthesis of alpha,alpha-difluorohomopropargyl alcohols containing an alkynyl silane moiety is reported. The ti tie compound was prepared by the reaction of the organozinc derivative of TIPS-bromodifluoropropyne with aldehydes or ketones under mild conditions and in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00196-9

文献信息

• Fluorinated Building Blocks. The Discovery of a Stable Difluoroallenyl Indium and the Synthesis of <i>g</i><i>em</i>-Difluoroallenyl and -propargyl Synthons in Aqueous Media
  作者：ZhiGang Wang、Gerald B. Hammond

  DOI：10.1021/jo000832f

  日期：2000.10.1

  The synthesis of two highly functional fluorinated motifs, TIPS-C triple bond C-CF2-, and CF2=C=C(TIPS)- is described. This approach is mediated by a room-temperature stable ethereal solution of a difluoroallene indium intermediate. This intermediate may be used as "stock solution" in the reaction with aqueous HCHO, to yield CF2=C=C(TIPS)CH2OH, and in a reaction with a Schiff base to produce the corresponding

  描述了两个功能性高的氟化基序TIPS-C三键C-CF2-和CF2 = C = C（TIPS）-的合成。这种方法是由室温稳定的二氟丙烯烯铟中间体的乙醚溶液介导的。该中间体可以在与HCHO水溶液反应中用作“原液”，以产生CF 2 ＝ C ＝ C（TIPS）CH 2 OH，并且在与席夫碱反应中以产生相应的β，β-二氟高炔丙基胺。CF2 = C = C（TIPS）CH2-OH的合成潜力已通过简便有效的5-内-trig环化反应转化为二氟二氢呋喃衍生物得到了证明。通过在主要为水的介质中将铟加到醛和TIPS-C三键C-CF2Br的混合物中，可以合成同炔的宝石二氟醇。
• On the Nature of Organoindium Intermediates: the Formation of Readily Isolable Difluoropropargylindium Reagents and their Regioselectivity Towards Electrophilic Substitutions
  作者：Bo Xu、Gerald B. Hammond

  DOI：10.1002/chem.200801367

  日期：2008.11.10

  The structure and reactivity of intermediate propargylindium complexes have been investigated. Their reaction with electrophiles produced a difluoroalkyne or -allene, depending on the nature of the electrophiles. A mechanism based on the Curtin-Hammett principle was invoked to explain this phenomenon. A newly proposed mechanism on the formation of indium(III) complexes, through the intermediacy of

  已经研究了中间体炔丙基鎓配合物的结构和反应性。它们与亲电试剂的反应产生了二氟炔或-丙二烯，具体取决于亲电试剂的性质。调用了基于Curtin-Hammett原理的机制来解释此现象。一种新提出的通过铟（I）物种形成中间体形成铟（III）的机理，可以帮助解释在醛存在下铟与1,1,1-二氟溴-2-炔烃的反应。
• Crystallographic Characterization of Difluoropropargyl Indium Bromide, a Reactive Fluoroorganometallic Reagent
  作者：Bo Xu、Mark S. Mashuta、Gerald B. Hammond

  DOI：10.1002/anie.200602823

  日期：2006.11.6
• Lanthanide Triflate-Catalyzed Preparation of β,β-Difluorohomopropargyl Alcohols in Aqueous Media. Application to the Synthesis of 4,4-Difluoroisochromans
  作者：Satoru Arimitsu、Gerald B. Hammond

  DOI：10.1021/jo0614588

  日期：2006.10.1

  An indium-mediated Barbier-type reaction of difluoropropargyl bromide with several aldehydes in aqueous media was enhanced by a catalytic amount of a lanthanide triflate (5 mol %). The reaction gave the corresponding beta,beta-difluorohomopropargyl alcohols with high regioselectivity. The [2 + 2 + 2] alkyne cyclotrimerization of beta,beta-difluorohomopropargyl alcohols with monosubstituted acetylenes produced 4,4-difluoroisochromans in good yields with moderate regioselectivity.
• Expedient synthesis of α,α-difluorohomopropargylic alcohols from TIPS-difluorobromopropyne via a Zn-mediated propargylation of aldehydes and ketones
  作者：ZhiGang Wang、Gerald B. Hammond

  DOI：10.1016/s0040-4039(00)00196-9

  日期：2000.4

  The synthesis of alpha,alpha-difluorohomopropargyl alcohols containing an alkynyl silane moiety is reported. The ti tie compound was prepared by the reaction of the organozinc derivative of TIPS-bromodifluoropropyne with aldehydes or ketones under mild conditions and in good yields. (C) 2000 Elsevier Science Ltd. All rights reserved.