2-Brom-1,1-diphenyl-propan-1-ol | 52072-24-9

• 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-Brom-1,1-diphenyl-propan-1-ol
• 英文别名: 2-Bromo-1,1-diphenylpropan-1-ol
• CAS: 52072-24-9
• 化学式: C₁₅H₁₅BrO
• 分子量: 291.187
• InChiKey: MNWGNWIZQTXKPO-UHFFFAOYSA-N

物化性质

• 熔点：
  57 °C(Solv: ethanol (64-17-5))
• 沸点：
  374.4±37.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• 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：
  1

反应信息

• 作为反应物：
  描述：

  2-Brom-1,1-diphenyl-propan-1-ol 在 溴 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 6.0h， 生成 (2-bromo-3,3-diphenylprop-2-en-1-yl)triphenylphosphonium bromide
  参考文献：
  名称：

  轴向手性N-杂环卡宾-Pd2 +配合物催化的异丙基苯磺酸不对称加成芳基硼酸

  摘要：

  异丙苯+卡宾=手性！N杂环卡宾-钯络合物催化将硼酸不对称地添加到异丙苯衍生物中，可提供所需的烯丙基产物，其收率良好至优异，对映选择性中等至良好。这些光学活性的烯丙基加合物可以以高收率和完整的手性被进一步转化为有用的手性产物（参见方案）。

  DOI：

  10.1002/chem.201100703
• 作为产物：
  描述：

  地芬尼多杂质9 在 溴 、 溶剂黄146 作用下， 反应 0.08h， 以59%的产率得到2-Brom-1,1-diphenyl-propan-1-ol
  参考文献：
  名称：

  Triflic imide-catalyzed cascade cycloaddition and Friedel–Crafts reaction of diarylvinylidenecyclopropanes with ethyl 5,5-diarylpenta-2,3,4-trienoate

  摘要：

  三氟甲基亚胺催化的级联环加成和Friedel-Crafts反应，将二芳基乙烯基环丙烷与乙基5,5-二芳基戊-2,3,4-三烯酸酯反应，在温和条件下提供了多种新颖的多环酯衍生物，产率中等至良好。

  DOI：

  10.1039/b903965a

文献信息

• Reaction of bromine with phenyl-substituted tertiary alcohols
  作者：Douglas W. Grant、Roy Shilton

  DOI：10.1039/p19740000135

  日期：——

  The reaction between bromine and 1,1-diphenylalkan-1-ols is shown to proceed by dehydration to an alkene, followed in aqueous acetic acid by formation of a bromohydrin which may then rearrange to a ketone. A number of new bromohydrins and bromoalkenes have been prepared.

  溴和1,1-二苯基烷烃-1-醇之间的反应显示为脱水成烯烃，然后在乙酸水溶液中形成溴代醇，然后再重排成酮，从而进行反应。已经制备了许多新的溴代醇和溴代烯烃。
• A Phosphine-Catalyzed Regioselective [3+2] Cycloaddition of Ethyl 5,5-Diarylpenta-2,3,4-trienoate with Aromatic Aldehydes and α,β-Unsaturated Carbonyl Compounds
  作者：Lu-Feng Wang、Xiao-Ping Cao、Zi-Fa Shi、Peng An、Hak-Fun Chow

  DOI：10.1002/adsc.201301000

  日期：2014.11.3

  AbstractTributylphosphine‐catalyzed regioselective [3+2] cycloadditions between ethyl 5,5‐diarylpenta‐2,3,4‐trienoate 1 and various aromatic aldehydes 2 to produce a wide variety of polysubstituted 2,5‐dihydrofurans 3, and between 1 and β‐unsubstituted α,β‐unsaturated carbonyl compounds 5 to give polysubstituted cyclopentenes 6 with a quaternary carbon center, are reported. In both cases the reaction partners approach each other via the sterically less hindered orientation to afford the target products in excellent regioselectivity. The reaction mechanism involved first the generation of a zwitterionic intermediate between the butatriene 1 and PBu3. For the formation of 2,5‐dihydrofurans 3, the preferred cyclization mode encompassed the nucleophilic attack of the α‐position of butatriene to the aldehydic carbon of 2, followed by the ring closure between the aldehydic oxygen of 2 and the γ‐position of butatriene, which is the first report of a normal [3+2] cycloaddition between cumulenes and aldehydes. For the formation of cyclopentenes 6, the reaction involved attack of the γ‐position of the butatriene to the electron‐deficient β‐position of the α,β‐unsaturated carbonyl compounds 5, followed by the ring closure between the α‐position of 5 and the α‐position of butatriene, which shows a different regioselectivity to the previously reported [3+2] cycloadditions between butatriene and olefins.magnified image
• Synthesis and reactions of allenic phosphonium salts and ylides
  作者：Kenneth Wayne Ratts、R. D. Partos

  DOI：10.1021/ja01050a031

  日期：1969.10
• FimZ Binds the<i>Salmonella typhimurium fimA</i>Promoter Region and May Regulate Its Own Expression with FimY
  作者：Kuang-sheng Yeh、Juliette K. Tinker、Steven Clegg

  DOI：10.1111/j.1348-0421.2002.tb02670.x

  日期：2002.1

  AbstractThe FimZ protein, an activator of FimA production in Salmonella typhimurium, acts in conjunction with FimY to facilitate the expression of type 1 fimbriae. The predicted amino acid sequence of FimZ suggests that this protein may be a DNA‐binding protein related to BvgA, a sensory regulator of virulence gene expression in Bordetella pertussis. Purification of FimZ following overexpression of the protein by a strong inducible promoter and gel mobility shift assays confirm that FimZ is a 25‐kDa polypeptide that binds to the promoter region of fimA. The region of DNA protected from DNase I digestion by FimZ binding is located between 47 and 98 nucleotides upstream from the fimA transcription initiation site. This region possesses a pair of 7‐base pair tandem repeats, of which at least one is necessary for FimZ binding. One copy of the 7‐base pair sequence is also located in the fimZ promoter region. In addition, expression from a fimZ‐lacZ reporter construct confirms that FimZ plays a role in its own expression. Both FimZ and FimY are required for high‐level expression of FimZ, which suggests that these two fimbrial proteins are involved in regulating both FimA and FimZ.
• Phosphine-Mediated [3+2] Cycloaddition Reactions of Ethyl 5,5-Diarylpenta-2,3,4-trienoates with Arylmethylidenemalononitriles and <i>N</i>-Tosylimines
  作者：Xiao-Yang Guan、Min Shi

  DOI：10.1021/jo802489t

  日期：2009.3.6

  Ethyl 5,5-diaryipenta-2,3,4-trienoates were synthesized and utilized in the phosphine-mediated [3+2] cycloaddition reactions with arylmethylidenemalononitriles and N-tosylimines in the presence of tributylphosphine. These reactions provide an easy access to a variety of novel polysubstituted cyclopentenes or pyrrolidines in good to excellent yields under mild conditions.