1-phenylprop-2-yn-1-yl pivalate

• 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-phenylprop-2-yn-1-yl pivalate
• 英文别名: 1-phenylprop-2-ynyl pivalate；1-phenylpropargyl pivaloate；1-Phenylprop-2-ynyl 2,2-dimethylpropanoate
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: QJVNSOIMAINTGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-phenylprop-2-yn-1-yl pivalate 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 bis(triphenylphosphine)palladium(II)-chloride 、 C₄₆H₃₀Au₂Cl₂F₆N₆ 、 silver trifluoromethanesulfonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 氘代氯仿 为溶剂， 反应 4.42h， 生成
  参考文献：
  名称：

  手性（无环二氨基卡宾）金（I）催化炔丙酯的动态不对称转化

  摘要：

  报道了手性（无环二氨基卡宾）金（I）配合物催化的高度对映选择性转化。开发了由外消旋苯酚取代的新戊酸炔丙酯对映选择性合成2-取代的新戊酸苯并苯酰的方法。在阳离子金存在下，底物重排得到丙二烯中间体，其环化导致通过动态动力学不对称转化形成对映体富集的产物。

  DOI：

  10.1021/ja205068j
• 作为产物：
  描述：

  1-苯基-3-三甲基硅烷-2-丙炔-1-醇 在 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 1-phenylprop-2-yn-1-yl pivalate
  参考文献：
  名称：

  Trialkyl Methanetricarboxylate as Dialkyl Malonate Surrogate in Copper-Catalyzed Enantioselective Propargylic Substitution

  摘要：

  The first copper-catalyzed enantioselective propargylation of trialkyl methantricarboxylate with propargylic alcohol derivatives was developed. The tricarboxylate unit in the obtained adducts could be easily transformed into a malonate moiety by treating with in situ generated NaOEt in excellent yield without racemization.

  DOI：

  10.1021/acs.orglett.5b02463

文献信息

• Synthesis of Pyrimidine-Containing Nucleoside β-(R/S)-Hydroxyphosphonate Analogues
  作者：Maïa Meurillon、Laurent Chaloin、Christian Périgaud、Suzanne Peyrottes

  DOI：10.1002/ejoc.201100219

  日期：2011.7

  β-hydroxyphosphonate analogues is described. The use of a nucleoside β-ketophosphonate as the key intermediate allowed both the (R) and (S) isomers of β-hydroxyphosphonate analogues in the pyrimidine series to be accessed. Such derivatives may be considered as stable mimics of 5

  描述了获得核苷 β-羟基膦酸酯类似物的简明途径。使用核苷 β-酮膦酸酯作为关键中间体允许获得嘧啶系列中 β-羟基膦酸酯类似物的 (R) 和 (S) 异构体。这样的衍生物可以被认为是 5
• Gold-catalyzed reactions of propargylic esters with vinylazides for the synthesis of Z- or E-configured buta-1,3-dien-2-yl esters
  作者：Sachin Bhausaheb Wagh、Rai-Shung Liu

  DOI：10.1039/c5cc05945c

  日期：——

  Gold-catalyzed synthesis of buta-1,3-dien-2-yl esters by the reaction of propargyl esters with vinylazides is described; the reaction mechanism is postulated to involve a vinyl attack of vinylazides at alkenyl gold carbenes.

  金催化合成丁-1,3-二烯-2-基酯的方法是通过丙炔基酯与乙烯叠氮化合物反应实现的；反应机理推测涉及乙烯叠氮化合物对烯基金卡宾的乙烯攻击。
• Gold(I)-Catalyzed Reactions of Propargyl Esters with Vinyl Derivatives
  作者：Christian A. Sperger、Jørn E. Tungen、Anne Fiksdahl

  DOI：10.1002/ejoc.201100291

  日期：2011.7

  A gold-catalyzed olefin cyclopropanation reaction of propargyl esters with vinyl ester or vinyl sulfonamide derivatives was investigated for the synthesis of highly substituted cyclopropane derivatives in good diastereoselectivity. By varying the vinyl species, trans-cyclopentenyl esters were selectively formed by a formal [3+2] cycloaddition.

  研究了炔丙酯与乙烯基酯或乙烯基磺酰胺衍生物的金催化烯烃环丙烷化反应，以合成具有良好非对映选择性的高度取代的环丙烷衍生物。通过改变乙烯基种类，通过正式的 [3+2] 环加成选择性地形成反式环戊烯酯。
• Synthesis of α-Acyloxyketone Derivatives <i>via</i> the Platinum-Catalyzed Migration of Propargylic Esters
  作者：Chihiro Tsukano、Sho Yamamoto、Yoshiji Takemoto

  DOI：10.1248/cpb.c15-00417

  日期：——

  The synthesis of α-acyloxyketones via the migration of a propargylic ester followed by the intramolecular nucleophilic addition of the resulting allene was achieved using a cationic platinum catalyst. The optimized conditions for this transformation were determined to be 3 mol% of Pt(cod)Cl2, 3 mol% of AgNTf2, and 3 eq of water in toluene at 100°C, and these conditions were successfully applied to the synthesis of a wide variety of α-aryl-α-acyloxyketones. The mechanism of this reaction was evaluated in detail based on the results of isotope labeling experiments using H218O.

  通过使用阳离子铂催化剂，实现了通过丙炔酯迁移随后进行所得丙二烯的分子内亲核加成来合成α-酰氧基酮的方法。确定这种转化的最佳条件为：3 mol%的Pt(cod)Cl2、3 mol%的AgNTf2和3 eq的水在100°C的甲苯中，这些条件成功应用于合成多种α-芳基-α-酰氧基酮。通过使用H218O的同位素标记实验结果，详细评估了该反应的机理。
• Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of <i>Anti</i>-δ,δ-Disubstituted Homoallylic Alcohols
  作者：Yoshikazu Horino、Miki Murakami、Ataru Aimono、Jun Hee Lee、Hitoshi Abe

  DOI：10.1021/acs.orglett.8b03761

  日期：2019.1.18

  The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF–H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical

  由三烷基硼烷/ O 2介导的炔烃末端具有三丁基锡烷基的炔丙基乙酸酯与醛在THF-H 2 O溶剂体系中的反应可得到具有良好或高非对映选择性的抗-δ，δ-二取代均烯丙基醇。有趣的是，两个衍生自三烷基硼烷的烷基被嵌入反应产物中。三烷基硼烷不仅起自由基引发剂的作用，而且作为烷基自由基的来源也起着关键作用。