methyl (3-methylnon-4-yn-3-yl) carbonate | 1609456-31-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: methyl (3-methylnon-4-yn-3-yl) carbonate
• 英文别名: Methyl 3-methylnon-4-yn-3-yl carbonate
• CAS: 1609456-31-6
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: GOQMRRCBBVKLCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (3-methylnon-4-yn-3-yl) carbonate 、 联硼酸频那醇酯 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以61%的产率得到4,4,5,5-tetramethyl-2-(3-methylnona-3,4-dien-5-yl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  Borylation of Propargylic Substrates by Bimetallic Catalysis. Synthesis of Allenyl, Propargylic, and Butadienyl Bpin Derivatives

  摘要：

  Bimetallic Pd/Cu and Pd/Ag catalytic systems were used for borylation of propargylic alcohol derivatives. The substrate scope includes even terminal alkynes. The reactions proceed stererospecifically with formal S(N)2' pathways to give allenyl boronates. Opening of propargyl epoxides leads to 1,2-diborylated butadienes probably via en allenylboronate intermediate.

  DOI：

  10.1021/ja502792s
• 作为产物：
  描述：

  1-己炔 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 methyl (3-methylnon-4-yn-3-yl) carbonate
  参考文献：
  名称：

  Borylation of Propargylic Substrates by Bimetallic Catalysis. Synthesis of Allenyl, Propargylic, and Butadienyl Bpin Derivatives

  摘要：

  Bimetallic Pd/Cu and Pd/Ag catalytic systems were used for borylation of propargylic alcohol derivatives. The substrate scope includes even terminal alkynes. The reactions proceed stererospecifically with formal S(N)2' pathways to give allenyl boronates. Opening of propargyl epoxides leads to 1,2-diborylated butadienes probably via en allenylboronate intermediate.

  DOI：

  10.1021/ja502792s

文献信息

• Synthesis of Allenes by Catalytic Coupling of Propargyl Carbonates with Aryl Iodides in the Presence of Diboron Species
  作者：Yuzhu Yang、Kálmán J. Szabó

  DOI：10.1021/acs.joc.5b01842

  日期：2016.1.4

  Bimetallic copper-/palladium-catalyzed multicomponent reaction of propargyl carbonates, aryl iodides, and diboron species was studied. This procedure can be used for synthesis of di-, tri-, and tetra-substituted allenes. Using diboronic acid, the reaction is supposed to proceed via allenylboronic acid intermediate.
• Switchable Regioselective C−H Activation/Annulation of Acrylamides with Alkynes for the Synthesis of 2‐Pyridones
  作者：Chao Chen、Yanni Chen、Zijian Han、Yujie Huang、Yujiao Wang、Xiuyu Tao、Lan Wang、Xiangli Chen、Ruikai Long、Yaxi Yang、Weiliang Zhu、Bing Zhou

  DOI：10.1002/cssc.202400066

  日期：——

  A catalyst‐based switchable regioselective C−H activation/annulation of acrylamides with propargyl carbonates has been developed, delivering C5 or C6 alkenyl substituted 2‐pyridones. This robust protocol proceeds with a broad substrate scope and good functional group tolerance under redox‐neutral reaction conditions. More significantly, this reaction is highly effective with previously challenging unsymmetrical alkynes, including unbiased alkyl‐alkyl substituted alkynes, with perfect and switchable regioselectivity. Additionally, mechanistic studies and DFT calculations were performed to shed light on the switchable regioselectivity.