1-(2-naphthyl)-4-(trimethylsilyl)-3-butyn-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-naphthyl)-4-(trimethylsilyl)-3-butyn-1-ol
• 英文别名: 1-Naphthalen-2-yl-4-trimethylsilylbut-3-yn-1-ol
• 化学式: C₁₇H₂₀OSi
• 分子量: 268.431
• InChiKey: BANYGKKWZLNORN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.14
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 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-(2-naphthyl)-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 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。
• Highly Regioselective Propargylation/Allenylation of Organolanthanum Reagents with Aldehydes
  作者：Xue-Lin Dai、Jingdi Ran、Thayalan Rajeshkumar、Zhengping Xu、Shanshan Liu、Zongchao Lv、Laurent Maron、Yi-Hung Chen

  DOI：10.1021/acs.orglett.3c00824

  日期：2023.5.5

  The metal-mediated propargylation or allenylation of carbonyl compounds is well-adapted to the preparation of homopropargylic or allenylic alcohols, which are multifunctional intermediates in synthetic chemistry. However, the regioselectivity of reactions using propargyl or allenyl metal reagents is difficult to control, owing to the equilibrium between the two species. In our study, propargyl or allenyl

  金属介导的羰基化合物炔丙基化或丙二烯基化非常适合制备均炔醇或丙二醇，它们是合成化学中的多功能中间体。然而，由于两种物质之间的平衡，使用炔丙基或联烯基金属试剂的反应的区域选择性难以控制。在我们的研究中，使用三甲基甲硅烷基丙炔或 prop-1-yn-1-ylbenzene 底物制备炔丙基或联烯基有机镧试剂。用醛处理有机镧试剂分别产生区域选择性产物。该研究提供了对稀土金属试剂的结构特异性和特殊化学选择性的更好理解。
• Regioselective Allene Synthesis and Propargylations with Propargyl Diethanolamine Boronates
  作者：Daniel R. Fandrick、Jonathan T. Reeves、Zhulin Tan、Heewon Lee、Jinhua J. Song、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1021/ol9022529

  日期：2009.12.3

  The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.
• Copper-Catalyst-Controlled Site-Selective Allenylation of Ketones and Aldehydes with Propargyl Boronates
  作者：Keith R. Fandrick、Junichi Ogikubo、Daniel R. Fandrick、Nitinchandra D. Patel、Jaideep Saha、Heewon Lee、Shengli Ma、Nelu Grinberg、Carl A. Busacca、Chris H. Senanayake

  DOI：10.1021/ol400124f

  日期：2013.3.15

  A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. The BPE ligand and boronate substituents were shown to direct the site selectivity for which either propargyl or allenyl adducts can be acquired in high selectivity. A model is proposed that explains the origin of the site selectivity.