6-phenylhex-3-en-5-yn-2-yl acetate | 138943-51-8

• 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: 6-phenylhex-3-en-5-yn-2-yl acetate
• CAS: 138943-51-8
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: UTUYKFPPWNRDND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-氧代环戊羧酸乙酯 、 6-phenylhex-3-en-5-yn-2-yl acetate 在 cobalt(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以46%的产率得到
  参考文献：
  名称：

  钴（II）与1,3-二羰基化合物与乙酸烯丙酯的烯丙基化反应

  摘要：

  在1,2-二氯乙烷中存在催化氯化钴（II）的情况下，可以用乙酸烯丙酯实现各种1,3-二羰基化合物的有效烯丙基化。

  DOI：

  10.1016/s0040-4039(00)73737-3
• 作为产物：
  描述：

  (+/-)-6-phenyl-hex-3ξ-en-5-yn-2-ol 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 生成 6-phenylhex-3-en-5-yn-2-yl acetate
  参考文献：
  名称：

  钴催化的1,3-二羰基化合物的区域选择性烯丙基化

  摘要：

  催化量的1,2-二氯乙烷中的氯化钴（II）以高收率促进1,3-二羰基化合物与乙酸烯丙酯的烯丙基化。与乙酰乙酸甲酯和2-氧代环戊烷甲酸乙酯相比，戊烷-2,4-二酮的烯丙基化具有高度的区域选择性。

  DOI：

  10.1016/s0040-4020(01)85380-1

文献信息

• Enantioselective C3‐Allylation of Pyridines via Tandem Borane and Palladium Catalysis
  作者：Jun‐Jie Tian、Rui‐Rui Li、Gui‐Xiu Tian、Xiao‐Chen Wang

  DOI：10.1002/anie.202307697

  日期：2023.8.21

  A one-pot, three-step method for highly enantioselective C3-allylation reactions of pyridines was developed. The method involved borane-catalyzed dearomative pyridine hydroboration, palladium-catalyzed enantioselective allylation of the dearomatized intermediate, and finally oxidation by air. The method was applicable to a broad range of pyridines, N-heteroarenes, and allylic esters.

  开发了一种用于吡啶的高度对映选择性 C3 烯丙基化反应的一锅三步方法。该方法包括硼烷催化的脱芳基吡啶硼氢化反应、钯催化的脱芳基中间体的对映选择性烯丙基化反应，以及最后的空气氧化反应。该方法适用于多种吡啶、N-杂芳烃和烯丙酯。
• Cobalt(II)-Catalyzed Conversion of Allylic Alcohols/Acetates to Allylic Amides in the Presence of Nitriles
  作者：Manoj Mukhopadhyay、M. Madhava Reddy、G. C. Maikap、Javed Iqbal

  DOI：10.1021/jo00114a013

  日期：1995.5

  Various secondary allylic alcohols or their acetates and tertiary allylic alcohols can be converted to the corresponding transposed allylic amides in the presence of a catalytic quantity of cobalt(II) chloride and acetic anhydride in acetonitrile. Tertiary alcohols undergo complete rearrangement whereas secondary ones afford a mixture of regioisomers. Moderate yields of amides are also obtained by reacting acrylonitrile with secondary alcohols in 1,2-dichloroethane. The presence of acetic anhydride or acetic acid is crucial to the formation of amides as the absence of the former affords no amides and the allylic alcohols are mainly recovered as regioisomeric mixtures. The regioselectivity during amide formation can be enhanced by using cobalt complexes 14-16 in acetic acid medium. Some preliminary studies indicate that these reactions are proceeding via an pi-allyl complex or tight ion pair rather than a [3,3] sigmatropic rearrangement of acetamidate obtained in a Pinner reaction.
• Cobalt catalyzed regioselective allylation of 1,3-dicarbonyl compounds
  作者：Golak C. Maikap、M. Madhava Reddy、Manoj Mukhopadhyay、Beena Bhatia、Javed Iqbal

  DOI：10.1016/s0040-4020(01)85380-1

  日期：1994.1

  Catalytic amount of Cobalt(II) chloride in 1,2-dichloroethane promotes the allylation of 1,3-dicarbonyl compounds with allyl acetates in high yields. The allylation of pentane-2,4-dione is highly regioselective as compared with methylacetoacetate and ethyl 2-oxocyclopentanecarboxylate.

  催化量的1,2-二氯乙烷中的氯化钴（II）以高收率促进1,3-二羰基化合物与乙酸烯丙酯的烯丙基化。与乙酰乙酸甲酯和2-氧代环戊烷甲酸乙酯相比，戊烷-2,4-二酮的烯丙基化具有高度的区域选择性。
• Cobalt (II) catalysed allylation of 1,3-dicarbonyl compounds with allyl acetates
  作者：Beena Bhatia、M.Madhava Reddy、Javed Iqbal

  DOI：10.1016/s0040-4039(00)73737-3

  日期：1993.9

  An efficient allylation of various 1,3-dicarbonyl compounds can be achived with allyl acetates in the presence of catalytic cobalt (II) chloride in 1,2-dichloroethane.

  在1,2-二氯乙烷中存在催化氯化钴（II）的情况下，可以用乙酸烯丙酯实现各种1,3-二羰基化合物的有效烯丙基化。