2,2-di(3-butynyl)malononitrile | 256424-52-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,2-di(3-butynyl)malononitrile
• 英文别名: 2,2-Bis(but-3-ynyl)propanedinitrile；2,2-bis(but-3-ynyl)propanedinitrile
• CAS: 256424-52-9
• 化学式: C₁₁H₁₀N₂
• 分子量: 170.214
• InChiKey: PXXXKNXAKROEPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-di(3-butynyl)malononitrile 在 decamethylrhenocene 作用下， 以 甲苯 为溶剂， 137.0 ℃ 、900.02 kPa 条件下， 生成 (-)-[7,7']-spiro-6,6',7,7'-tetrahydro-bis-5H-cyclopenta[b]pyridine
  参考文献：
  名称：

  One-Step Synthesis of Spiropyridines, a Novel Class of C₂-Symmetric Chiral Ligands, by Cobalt(I)-Catalyzed [2 + 2 + 2] Cycloadditions between Bis-Alkynenitriles and Alkynes

  摘要：

  Spiropyridines, a novel series of C-2-symmetric ligands, can be obtained in moderate yields by means of Co(l) catalyzed double cocyclization between bis-alkynenitriles and alkynes. This one-step method allowed the first synthesis of the interesting 7,7'- and 8,8'-spyropyridines from acyclic precursors.

  DOI：

  10.1021/ol991195m
• 作为产物：
  描述：

  对甲苯磺酸 3-丁炔酯 、 1,1-dicyano-4-pentyne 在 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 以66%的产率得到2,2-di(3-butynyl)malononitrile
  参考文献：
  名称：

  One-Step Synthesis of Spiropyridines, a Novel Class of C₂-Symmetric Chiral Ligands, by Cobalt(I)-Catalyzed [2 + 2 + 2] Cycloadditions between Bis-Alkynenitriles and Alkynes

  摘要：

  Spiropyridines, a novel series of C-2-symmetric ligands, can be obtained in moderate yields by means of Co(l) catalyzed double cocyclization between bis-alkynenitriles and alkynes. This one-step method allowed the first synthesis of the interesting 7,7'- and 8,8'-spyropyridines from acyclic precursors.

  DOI：

  10.1021/ol991195m

文献信息

• Enantioselective Synthesis of Pyridines with All‐Carbon Quaternary Carbon Centers via Cobalt‐Catalyzed Desymmetric [2+2+2] Cycloaddition
  作者：Ke Li、Linsheng Wei、Minghe Sun、Bing Li、Min Liu、Changkun Li

  DOI：10.1002/anie.202105452

  日期：2021.9.6

  A Co-catalyzed enantioselective desymmetric [2+2+2] cycloaddition for synthesis of pyridines with all-carbon quaternary carbon centers has been developed. The regio- and enantioselectivities are controlled by the inherent nature of terminal alkynes and the substituents on the bisoxazolinephosphine ligands. Pyridines with 5-substitutents could be obtained with >20:1 regioselectivity and up to 94 % ee

  已经开发了一种用于合成具有全碳季碳中心的吡啶的共催化对映选择性去对称 [2+2+2] 环加成反应。区域选择性和对映选择性受末端炔烃和双恶唑啉膦配体上的取代基的固有性质控制。当使用末端烷基、烯基或甲硅烷基炔烃和基于 DTBM/Ph 的 NPN* 配体L6时，可以获得具有 5-取代基的吡啶，区域选择性 >20:1，ee高达 94% 。末端芳基炔烃和基于 Ph/Bn 的配体L4导致形成具有高达 99% ee 的6-取代基的吡啶。
• Poly(N-vinylimidazole) as efficient recyclable catalyst for the Michael addition of CH-acids to electron deficient alkenes in water
  作者：E. A. Tarasenko、V. S. Tyurin、F. Lamaty、I. P. Beletskaya

  DOI：10.1007/s11172-011-0401-7

  日期：2011.12

  Efficiency of poly(N-vinylimidazole) as the basic recyclable catalyst for the Michael addition of CH-acids to acrylonitrile, methyl acrylate, methyl vinyl ketone and methyl vinyl sulfone in water at ambient temperature was studied. In these reactions, formation of both 1: 1 and 1: 2 adducts is possible.

  研究了聚（N-乙烯基咪唑）作为碱性可回收催化剂的效率，用于在环境温度下将 CH 酸与丙烯腈、丙烯酸甲酯、甲基乙烯基酮和甲基乙烯基砜在水中进行迈克尔加成。在这些反应中，可能形成 1:1 和 1:2 加合物。
• One-Step Synthesis of Spiropyridines, a Novel Class of <i>C</i>₂-Symmetric Chiral Ligands, by Cobalt(I)-Catalyzed [2 + 2 + 2] Cycloadditions between Bis-Alkynenitriles and Alkynes
  作者：Jesús A. Varela、Luis Castedo、Carlos Saá

  DOI：10.1021/ol991195m

  日期：1999.12.1

  Spiropyridines, a novel series of C-2-symmetric ligands, can be obtained in moderate yields by means of Co(l) catalyzed double cocyclization between bis-alkynenitriles and alkynes. This one-step method allowed the first synthesis of the interesting 7,7'- and 8,8'-spyropyridines from acyclic precursors.