3-methyl-3-[6-(2,2'-dipiridyl)]ethylbutanoate | 305819-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-methyl-3-[6-(2,2'-dipiridyl)]ethylbutanoate
• 英文别名: Ethyl 3-methyl-3-(6-pyridin-2-ylpyridin-2-yl)butanoate；ethyl 3-methyl-3-(6-pyridin-2-ylpyridin-2-yl)butanoate
• CAS: 305819-33-4
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: KAWLPQULXKURBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 CO 作用下， 以 乙醇 为溶剂， 以20%的产率得到3-methyl-3-[6-(2,2'-dipiridyl)]ethylbutanoate
  参考文献：
  名称：

  Cyclopalladation of 6-Substituted-2,2‘-bipyridines. Metalation of Unactivated Methyl Groups vs Aromatic C−H Activation

  摘要：

  6-Alkyl-2,2'-bipyridines, HL, (N2C10H7R; R = CH2Me, HLet; CHMe2, HLip; CMe3, HLtb, CH2CMe3, HLnp, CMe2Ph, HLdm) react with Na-2[PdCl4] to give either 1:1 adducts [Pd(HL)Cl-2] (HLet, HLip, HLnp) or cyclometalated complexes [Pd(L)Cl] (HLtb, HLdm). Reaction of palladium(II) acetate, followed by exchange with LiCl, affords a series of cyclopalladated species [Pd(L)Cl] where L is a terdentate anionic N-N-C ligand which originates from HL through direct activation of a C(sp(3))-H or a C(sp(2))-H bond. The structures of [Pd(L-tb)Cl] and [Pd(L-np)Cl], which contain a [5,5] ora [5,6] fused ring system, respectively, have been determined by X-ray diffraction and are compared. In the case of the ligand HLip, three different cyclometalated species have been isolated, [Pd(L)Cl], [Pd(L)Cl](2), and [Pd{N2C10H7[CH(CH2-OC(O)CH3)(CH2)}Cl] the latter one arising from activation of both methyl groups of the substituent. The isolation of two [Pd(L-dm)Cl] species (compounds 8 and 9), having an aromatic or an aliphatic carbon-metal bond, respectively, is an example of isomerism, still rare in organometallic chemistry.

  DOI：

  10.1021/om000239o

文献信息

• Cyclopalladation of 6-Substituted-2,2‘-bipyridines. Metalation of Unactivated Methyl Groups vs Aromatic C−H Activation
  作者：Antonio Zucca、Maria Agostina Cinellu、Maria Vittoria Pinna、Sergio Stoccoro、Giovanni Minghetti、Mario Manassero、Mirella Sansoni

  DOI：10.1021/om000239o

  日期：2000.10.1

  6-Alkyl-2,2'-bipyridines, HL, (N2C10H7R; R = CH2Me, HLet; CHMe2, HLip; CMe3, HLtb, CH2CMe3, HLnp, CMe2Ph, HLdm) react with Na-2[PdCl4] to give either 1:1 adducts [Pd(HL)Cl-2] (HLet, HLip, HLnp) or cyclometalated complexes [Pd(L)Cl] (HLtb, HLdm). Reaction of palladium(II) acetate, followed by exchange with LiCl, affords a series of cyclopalladated species [Pd(L)Cl] where L is a terdentate anionic N-N-C ligand which originates from HL through direct activation of a C(sp(3))-H or a C(sp(2))-H bond. The structures of [Pd(L-tb)Cl] and [Pd(L-np)Cl], which contain a [5,5] ora [5,6] fused ring system, respectively, have been determined by X-ray diffraction and are compared. In the case of the ligand HLip, three different cyclometalated species have been isolated, [Pd(L)Cl], [Pd(L)Cl](2), and [PdN2C10H7[CH(CH2-OC(O)CH3)(CH2)}Cl] the latter one arising from activation of both methyl groups of the substituent. The isolation of two [Pd(L-dm)Cl] species (compounds 8 and 9), having an aromatic or an aliphatic carbon-metal bond, respectively, is an example of isomerism, still rare in organometallic chemistry.