1-oxo-1-phenyl-3-(tert-butyldimethylsilyl)prop-2-yne

• 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-oxo-1-phenyl-3-(tert-butyldimethylsilyl)prop-2-yne
• 英文别名: 3-(tert-butyldimethylsilyl)-1-phenylprop-2-yn-1-one；3-(t-butyldimethylsilyl)-1-phenylprop-2-yn-1-one；3-(tert-Butyldimethylsilanyl)-1-phenylpropynone；3-[Tert-butyl(dimethyl)silyl]-1-phenylprop-2-yn-1-one
• 化学式: C₁₅H₂₀OSi
• 分子量: 244.409
• InChiKey: VRVWOQPPPVYRJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-oxo-1-phenyl-3-(tert-butyldimethylsilyl)prop-2-yne 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 3-(tert-butyldimethylsilyl)-1-phenylprop-2-yn-1-ol
  参考文献：
  名称：

  Developing asymmetric iron and ruthenium-based cyclone complexes; complex factors influence the asymmetric induction in the transfer hydrogenation of ketones

  摘要：

  本文描述了一系列非对称铁和钌-环辛四烯复合物的制备及其在酮不对称还原中的应用。酮还原的立体选择性受到催化剂中单个手性中心以及催化剂中平面手性的影响。这代表了首次使用铁环辛四烯催化剂进行酮不对称还原的实例。

  DOI：

  10.1039/c1ob06010d
• 作为产物：
  描述：

  (+/-)-1-苯基-2-丙炔-1-醇 在 manganese(IV) oxide 、 正丁基锂 、 对甲苯磺酸一水合物 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 79.0h， 生成 1-oxo-1-phenyl-3-(tert-butyldimethylsilyl)prop-2-yne
  参考文献：
  名称：

  Indium-Catalyzed [2 + 2] Cycloaddition of Allylsilanes to Internal Alkynones

  摘要：

  We have developed an indium-catalyzed [2 + 2] cydo-addition of allylsilanes to alkynones leading to selective cydobutenone formation. The resulting cydobutenones were readily converted to the oxidized products by Tamao-Fleming oxidation or the ring-opened products by an electrocyclic reaction.

  DOI：

  10.1021/acs.orglett.5b03065

文献信息

• Transition-Metal-Free Synthesis of Ynones via Decarboxylative Alkynylation of α-Keto Acids under Mild Conditions
  作者：Peng-Fei Wang、Yi-Si Feng、Zhi-Fei Cheng、Qiu-Min Wu、Guang-Yu Wang、Liang-Liang Liu、Jian-Jun Dai、Jun Xu、Hua-Jian Xu

  DOI：10.1021/acs.joc.5b01387

  日期：2015.9.18

  A transition-metal-free synthetic method of various ynones via decarboxylative alkynylation of α-keto acids is described. The reaction is carried out under mild conditions and exhibits remarkable tolerance of functional groups. The mechanism of a radical process is proposed in the reaction.

  描述了通过α-酮酸的脱羧炔基化反应的各种炔酮的无过渡金属合成方法。该反应在温和的条件下进行，并表现出显着的官能团耐受性。在反应中提出了自由基过程的机理。
• Decarboxylative Alkynylation of α-Keto Acids and Oxamic Acids in Aqueous Media
  作者：Hua Wang、Li−Na Guo、Shun Wang、Xin-Hua Duan

  DOI：10.1021/acs.orglett.5b01336

  日期：2015.6.19

  K2S2O8 promoted decarboxylative alkynylation of α-keto acids and oxamic acids has been developed. This process features mild reaction conditions, a broad substrate scope, and good functional-group tolerance, therefore providing a new and efficient access to a wide range of ynones and propiolamides. Furthermore, this radical process could also be successfully applied to alkynylation of the Csp2–H bond

  已经开发出温和的K 2 S 2 O 8促进α-酮酸和草酰胺酸的脱羧炔基化。该工艺具有温和的反应条件，广泛的底物范围和良好的官能团耐受性，因此提供了一种新型且有效的途径，可广泛使用炔酮和丙酰胺类化合物。此外，该自由基过程也可以成功地用于高价炔碘试剂对DMF中C sp 2 -H键的炔基化反应。
• Room temperature palladium catalysed coupling of acyl chlorides with terminal alkynes
  作者：Russell J. Cox、Dougal J. Ritson、Thomas A. Dane、John Berge、Jonathan P. H. Charmant、Anob Kantacha

  DOI：10.1039/b414826f

  日期：——

  Conditions are reported for the facile, high-yielding coupling of acyl chlorides with terminal alkynes in a reaction involving palladium and copper iodide; the reaction is tolerant of a wide variety of acyl chlorides and terminal alkynes and provides a convenient one-pot route to acetylenic ketones.

  报道了在涉及钯和碘化铜的反应中酰氯与末端炔烃的容易，高产偶联的条件。该反应可耐受各种酰氯和末端炔烃，并为炔酮提供了便捷的一锅法。
• Cationic-Oxazaborolidine-Catalyzed Enantioselective Diels-Alder Reaction of α,β-Unsaturated Acetylenic Ketones
  作者：Joshua N. Payette、Hisashi Yamamoto

  DOI：10.1002/anie.200904339

  日期：2009.10.12

  Yne also a good dienophile: The cationic oxazaborolidine 1 promoted the formation of Diels–Alder adducts between acetylenic ketones and both cyclic and acyclic dienes in excellent yield with 99 % ee (see scheme; Tf=trifluoromethanesulfonyl, TMS=trimethylsilyl). Importantly, high levels of asymmetric induction were also observed with dienophiles that lacked the typical hydrogen‐bonding motif required

  炔也是很好的亲双烯体：阳离子恶唑硼烷1推动的炔酮和环状和无环二烯烃之间狄尔斯-阿德耳加合物的形成的优良率以99％的 ee值（参见方案; TF =三氟甲磺酰基，TMS =三甲基甲硅烷）。重要的是，在缺乏其他 oxazaborolidinium 介导的反应所需的典型氢键基序的亲二烯体中也观察到了高水平的不对称诱导。
• Rhodium-Catalyzed Chemo- and Enantioselective Hydrogenation of Alkynyl-Aryl Hydrazones
  作者：Dongyang Fan、Yanhua Hu、Feng Jiang、Zhenfeng Zhang、Wanbin Zhang

  DOI：10.1002/adsc.201800243

  日期：2018.6.5

  As an update of our continuous interest in the hydrogenation of hydrazones, a chemo‐ and enantioselective hydrogenation of alkynyl‐aryl hydrazones was developed using a rhodium complex [Rh((R,Sp)‐JosiPhos)(cod)]SbF6 as the catalyst and benzoic acid as an additive. Directed by a p‐nitrobenzamido group, the chiral propargyl hydrazines, which can be easily converted to chiral propargylamines of significant

  为了不断提高对hydr的氢化的兴趣，使用铑配合物[Rh（（R，Sp）-JosiPhos）（cod）] SbF 6作为催化剂开发了炔基-芳基的化学和对映选择性氢化和苯甲酸作为添加剂。由p指示‐硝基苯甲酰胺基，手性炔丙基肼，可以容易地转化为具有重要意义和潜在用途的手性炔丙基胺，收率高，化学选择性好，对映选择性好。尽管反应的对映选择性和底物/催化剂的比例需要进一步完善，但是所报道的方法为有效制备手性炔丙基胺提供了另一种途径。