methyl 5-phenylpent-1-yn-3-yl carbonate | 880085-52-9

• 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: methyl 5-phenylpent-1-yn-3-yl carbonate
• 英文别名: methyl 5-phenyl-1-pentyn-3-yl carbonate
• CAS: 880085-52-9
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: UALNPJMTUXOXAY-UHFFFAOYSA-N

物化性质

• 沸点：
  305.9±42.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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 5-phenylpent-1-yn-3-yl carbonate 、 反式-苯乙烯三氟硼酸钾 在 四(三苯基膦)钯 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 以70%的产率得到1,7-diphenyl-1,3,4-heptatriene
  参考文献：
  名称：

  Palladium(0)-Catalyzed Synthesis of Chiral Ene-allenes Using Alkenyl Trifluoroborates

  摘要：

  [GRAPHICS]Enantioenriched allenes serve as chiral transfer reagents, making them attractive synthetic targets. Herein, the synthesis of enantioenriched allenes utilizing a Pd(O)-catalyzed cross-coupling reaction of propargylic carbonates and phosphates with alkenyl trifluoroborates is reported. Di-, tri-, and tetrasubstituted allenes were synthesized in moderate to high optical yields. Several racemic allenes possessing various functional groups were also synthesized.

  DOI：

  10.1021/jo052201x
• 作为产物：
  描述：

  5-phenylpent-1-yn-3-ol 、 氯甲酸甲酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以67%的产率得到methyl 5-phenylpent-1-yn-3-yl carbonate
  参考文献：
  名称：

  Palladium(0)-Catalyzed Synthesis of Chiral Ene-allenes Using Alkenyl Trifluoroborates

  摘要：

  [GRAPHICS]Enantioenriched allenes serve as chiral transfer reagents, making them attractive synthetic targets. Herein, the synthesis of enantioenriched allenes utilizing a Pd(O)-catalyzed cross-coupling reaction of propargylic carbonates and phosphates with alkenyl trifluoroborates is reported. Di-, tri-, and tetrasubstituted allenes were synthesized in moderate to high optical yields. Several racemic allenes possessing various functional groups were also synthesized.

  DOI：

  10.1021/jo052201x

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.
• Rhodium-Catalyzed Propargylic Substitution: A Divergent Approach to Propargylic and Allenyl Sulfonamides
  作者：P. Andrew Evans、Michael J. Lawler

  DOI：10.1002/anie.200600615

  日期：2006.7.24
• Palladium(0)-Catalyzed Synthesis of Chiral Ene-allenes Using Alkenyl Trifluoroborates
  作者：Gary A. Molander、Erin M. Sommers、Sharon R. Neufeldt

  DOI：10.1021/jo052201x

  日期：2006.2.17

  [GRAPHICS]Enantioenriched allenes serve as chiral transfer reagents, making them attractive synthetic targets. Herein, the synthesis of enantioenriched allenes utilizing a Pd(O)-catalyzed cross-coupling reaction of propargylic carbonates and phosphates with alkenyl trifluoroborates is reported. Di-, tri-, and tetrasubstituted allenes were synthesized in moderate to high optical yields. Several racemic allenes possessing various functional groups were also synthesized.