1-methyl-1-phenyl-4-(trimethylsilyl)-3-butyn-1-ol | 67448-60-6

• 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: 1-methyl-1-phenyl-4-(trimethylsilyl)-3-butyn-1-ol
• 英文别名: 2-Phenyl-5-(trimethylsilyl)pent-4-yn-2-ol；2-phenyl-5-trimethylsilylpent-4-yn-2-ol
• CAS: 67448-60-6
• 化学式: C₁₄H₂₀OSi
• 分子量: 232.398
• InChiKey: WRJZRANAMDPBNI-UHFFFAOYSA-N

物化性质

• 沸点：
  308.0±35.0 °C(Predicted)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1-methyl-1-phenyl-4-(trimethylsilyl)-3-butyn-1-ol 在 potassium carbonate 、 水 作用下， 以 甲醇 、 醋酸异丙酯 为溶剂， 反应 1.0h， 以1.41 g的产率得到2-phenylpent-4-yn-2-ol
  参考文献：
  名称：

  Zinc Catalyzed and Mediated Propargylations with Propargyl Boronates

  摘要：

  The utility of allenyl and propargyl boronates for the propargylation of aldehydes and ketones mediated by zinc is presented. The reaction Is catalytic in zinc with allenyl or propargyl borolanes. The propargylation with crystalline and air-stable propargyl diethanolamine boronates was also achieved. A catalytic cycle is proposed, and preliminary mechanistic studies are discussed.

  DOI：

  10.1021/ol902457m
• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 在 正丁基锂 、 水 作用下， 反应 6.0h， 生成 1-methyl-1-phenyl-4-(trimethylsilyl)-3-butyn-1-ol
  参考文献：
  名称：

  Application of elementoorganic compounds of 15th and 16th Groups in organic synthesis. 100. Reactions of carbonyl compounds with [(trimethylsilyl)propargyl]diisobutyltelluronium bromide mediated by different strong bases: highly regioselective synthesis of (trimethylsilyl)propargyl alcohols and highly stereoselective synthesis of cis-(trimethylsilyl)alkynyl epoxides

  摘要：

  [(Trimethylsilyl)propargyl)]diisobutyltelluronium bromide (1), after being treated with alkyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species reacts with carbonyl compounds to give (trimethylsilyl)propargyl alcohols 2 in high yields with high regioselectivity. However, when the telluronium salt 1 was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed. The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl) alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity.

  DOI：

  10.1021/jo00050a042

文献信息

• Regioselective Addition Reactions of Propargyl Bromides to Carbonyl Compounds with Gallium Catalyzed by Indium
  作者：Phil Ho Lee、Hyun Kim、Kooyeon Lee

  DOI：10.1002/adsc.200505046

  日期：2005.7

  propargyl bromides having substituents at the γ-position and gallium in the presence of 5 mol % of indium with aldehydes and ketones selectively produced homoallenyl alcohols in good to excellent yields. Treatment of organogallium reagents obtained from propargyl bromide or propargyl bromides having substituents at the α-position and gallium in the presence of 5 mol % of indium with carbonyl compounds selectively

  在5mol％的铟存在下，由在γ-位具有取代基的炔丙基溴和镓产生的有机镓试剂与醛和酮的反应选择性地以良好或优异的产率产生了高均烯基醇。在5mol％的铟存在下，用羰基化合物处理由在α位具有取代基的炔丙基溴或炔丙基溴和镓获得的有机镓试剂，选择性地得到高炔丙醇。
• Gallium-mediated highly regioselective reactions of trimethylsilylpropargyl bromide and trimethylsilylallyl bromide with carbonyl compounds
  作者：Ying Han、Yao-Zeng Huang

  DOI：10.1016/s0040-4039(00)78562-5

  日期：1994.12

  One-pot reactions of gallium powder, trimethylsilylpropargyl bromide, aldehydes or ketones in the presence of KI and LiCl show very high acetylenic selectivity and under the same conditions, trimethylsilylallyl bromide also exhibits very high selectivity favoring α-adducts.

  镓粉，三甲基甲硅烷基炔丙基溴，醛或酮在KI和LiCl存在下的一锅反应显示出很高的炔属选择性，在相同条件下，三甲基甲硅烷基烯丙基溴也表现出非常高的选择性，有利于α加合物。
• Selective multiple methylene insertion reactions mediated by iodomethylzine iodide: Mechanistic considerations and synthetic applications
  作者：Michael J. Rozema、Paul Knochel

  DOI：10.1016/s0040-4039(00)85980-8

  日期：1991.4

  The reaction of alkynylcoppers 1 with an excess of iodomethylzinc iodide selectively furnishes the quadruple methylene insertion copper organometallics 2 in fair to good yields. The mechanism of the reaction has been investigated and postulated intermediates such as 4 or 8 have been trapped with electrophiles like aldehydes or ketones in excellent yields. A new in situ preparation of propargylic copper

  炔基铜1与过量的碘代甲基碘化锌的反应选择性地以公平至良好的产率提供了四重亚甲基插入铜有机金属化合物2。已经研究了反应的机理，并且假定的中间体（如4或8）已被亲电子试剂（如醛或酮）以优异的产率捕获。已经开发了一种新的就地制备炔丙基铜衍生物4的方法，该方法从易于获得的炔铜化合物开始，从而以80-95％的收率制得了均炔丙基醇。
• Regioselective Propargylation of Carbonyl Compounds with (3-Bromoprop-1-ynyl)trimethylsilane Promoted by Reactive Barium
  作者：Akira Yanagisawa、Shogo Okitsu、Takayoshi Arai

  DOI：10.1055/s-2005-869874

  日期：——

  A Barbier-type propargylation of aldehydes with (3-bromoprop-1-ynyl)trimethylsilane has been achieved using reactive barium as a low-valent metal in THF. This process is effective also for obtaining the desired homopropargylic alcohols in high yields from the corresponding ketones including enolizable ketones such as cyclopent-2-enone.

  在 THF 中使用活性钡作为低价金属，实现了醛与 (3-bromoprop-1-ynyl)trimethylsilane 的巴比尔式丙炔化反应。该工艺还能有效地从相应的酮类（包括环戊-2-烯酮等可烯化的酮类）中高产率地获得所需的均丙炔醇。
• Eiter,K. et al., Justus Liebigs Annalen der Chemie, 1978, p. 658 - 674
  作者：Eiter,K. et al.

  DOI：——

  日期：——