1-methoxy-3-heptyne | 1111192-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methoxy-3-heptyne
• 英文别名: 1-Methoxyhept-3-yne
• CAS: 1111192-56-3
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: XSXVROAAFQONQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methoxy-3-heptyne 、 2-cyanophenyl 4-(dimethylamino)benzoate 在 bis(1,5-cyclooctadiene)nickel (0) 、 甲铝双(2,6-二叔丁基-4-苯甲醚) 、 三苄基膦 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 4-(2-methoxyethyl)-3-propyl-2H-chromen-2-one 、 3-(2-methoxyethyl)-4-propyl-2H-chromen-2-one
  参考文献：
  名称：

  Nickel-Catalyzed Cycloaddition ofo-Arylcarboxybenzonitriles and Alkynes via Cleavage of Two Carbon–Carbon σ Bonds

  摘要：

  An intermolecular cycloaddition reaction has been developed, where o-arylcarboxybenzonitriles react with alkynes to afford coumarins in the presence of Ni(0)/P(CH(2)Ph)(3)/MAD as a catalyst. The reaction process displays an unusual mechanistic feature the cleavage of two independent C-CN and C-CO bonds.

  DOI：

  10.1021/ja203829j

文献信息

• Nickel-catalyzed [2+2+1] cycloaddition of alkynes, acrylates and isocyanates
  作者：Takuya Ozawa、Hiroaki Horie、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1039/c0cc02613a

  日期：——

  Intermolecular [2+2+1] cycloaddition which incorporates an alkyne, an isocyanate, and an alkene into a gamma-butyrolactam proceeds with nickel catalyst.

  用镍催化剂进行将炔，异氰酸酯和烯烃结合到γ-丁内酰胺中的分子间[2 + 2 + 1]环加成反应。
• Synthesis of Quinolones by Nickel-Catalyzed Cycloaddition via Elimination of Nitrile
  作者：Kenichiro Nakai、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/ol303546p

  日期：2013.2.15

  Substituted quinolones were efficiently synthesized via the nickel-catalyzed cycloaddition of o-cyanophenylbenzamide derivatives with alkynes. The reaction involves elimination of a nitrile group by cleavage of the two independent aryl–cyano and aryl–carbonyl C–C bonds of the amides.

  通过邻位氰基苯基苯甲酰胺衍生物与炔烃的镍催化环加成反应可高效合成取代的喹诺酮。该反应涉及通过裂解酰胺的两个独立的芳基-氰基和芳基-羰基CC键来消除腈基。
• Nickel-catalyzed dual C–C σ bond activation to construct carbocyclic skeletons
  作者：Kenichiro Nakai、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1016/j.tet.2015.02.064

  日期：2015.7

  A nickel/Lewis acid catalyzed intermolecular cycloaddition reaction of o-cyanobenzylarylketones with allcynes to form naphthalenones is developed. This reaction is promoted by the nickel/Lewis Acid catalyst pair and involves the cleavage of two C-C sigma bonds to eliminate arylcyanide and the formation of different two C-C sigma bonds with alkyne insertion. (C) 2015 Elsevier Ltd. All rights reserved.
• Nickel-Catalyzed Redox-Economical Coupling of Alcohols and Alkynes to Form Allylic Alcohols
  作者：Kenichiro Nakai、Yuji Yoshida、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/ja500666h

  日期：2014.6.4

  We have developed a redox-economical coupling reaction of alcohols and alkynes to form allylic alcohols under mild conditions. The reaction is redox-neutral as well as redox-economical and thus free from any additives such as a reductant or an oxidant. This atom-economical coupling can be applied for the conversion of both aliphatic and benzylic alcohols to the corresponding substituted allylic alcohols in a single synthetic operation.
• Nickel-Catalyzed Cycloaddition of Anthranilic Acid Derivatives to Alkynes
  作者：Nobuyoshi Maizuru、Tasuku Inami、Takuya Kurahashi、Seijiro Matsubara

  DOI：10.1021/ol200090g

  日期：2011.3.4

  A nickel-catalyzed cycloaddition has been developed where readily available anthranilic acid derivatives react with alkynes to afford substituted indoles. The reaction involves oxidative addition of Ni(0) to an ester moiety, which allows intermolecular addition to alkynes via decarbonylation and 1,3-acyl migration.