Yb(O[2,6-di-tert-butyl-4-(methyl)C₆H₂])₃(tetrahydrofuran)₂ | 1280214-96-1

• 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: Yb(O[2,6-di-tert-butyl-4-(methyl)C₆H₂])₃(tetrahydrofuran)₂
• 英文别名: (2,6-tBu2-4-MeC6H2O)3Yb(THF)2；Yb(O(2,6-tBu₂-4-MeC₆H₂))₃(THF)₂；[Yb(OC6H2-4-Me-2,6-(t-Bu)2)3(THF)2]；2,6-Ditert-butyl-4-methylphenolate;oxolane;ytterbium(3+)；2,6-ditert-butyl-4-methylphenolate;oxolane;ytterbium(3+)
• CAS: 1280214-96-1
• 化学式: C₅₃H₈₅O₅Yb
• 分子量: 975.295
• InChiKey: QORMENVUXNCHAC-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  12.58
• 重原子数：
  59
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  87.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Yb(O[2,6-di-tert-butyl-4-(methyl)C₆H₂])₃(tetrahydrofuran)₂ 、 N,N'-二异丙基碳二亚胺 以 甲苯 为溶剂， 以78%的产率得到[Yb(OC6H2-4-Me-2,6-(t-Bu)2)3(N,N'-diisopropylcarbodiimide)]
  参考文献：
  名称：

  Activation of Carbodiimide and Transformation with Amine to Guanidinate Group by Ln(OAr)₃(THF)₂ (Ln: Lanthanide and Yttrium) and Ln(OAr)₃(THF)₂ as a Novel Precatalyst for Addition of Amines to Carbodiimides: Influence of Aryloxide Group

  摘要：

  Reaction of Ln(OAr1)(3)(THF)(2) (Ar-1 = [2,6-(Bu-t)(2)-4-MeC6H2] with carbodiimides (RNCNR) in toluene afforded the RNCNR coordinated complexes ((ArO)-O-1)(3)Ln(NCNR) (R = Pr-i (isopropyl), Ln = Y (1) and Yb (2); R = Cy (cyclohexyl), Ln = Y (3)) in high yields. Treatment of 1 and 2, with 4-chloroaniline, respectively, at a molar ratio of 1:1 yielded the corresponding monoguanidinate complex ((ArO)-O-1)(2)Y[(4-Cl-C6H4N)C((NHPr)-Pr-i) (NPr)-Pr-i](THF) (4) and ((ArO)-O-1)(2)Yb[(4-Cl-C6H4N)C((NHPr)-Pr-i)(NPr)-Pr-i] (THF) (5). Complexes 4 and 5 can be prepared by the reaction of Ln(OAr1)(3)(THF)(2) with RNCNR and amine in toluene at a 1:1:1 molar ratio in high yield directly. A remarkable influence of the aryloxide ligand on this transformation was observed. The similar transformation using the less bulky yttrium complexes Y(OAr2)(3)(THF)(2) (Ar-2 = [2,6-(Pr-i)(2)C6H3]) or Y(OAr3)(3)(THF)(2) (Ar-3 = [2,6-Me2C6H3]) did not occur. Complexes Ln(OAr1)(3)(THF)(2) were found to be the novel precatalysts for addition of RNCNR with amines, which represents the first example of catalytic guanylation by the lanthanide complexes with the Ln-O active group. The catalytic activity of Y(OAr1)(3)(THF)(2) was found to be the same as that of monoguanidinate complex 4, indicating 4 is one of the active intermediates in the present process. The other intermediate, amide complex ((ArO)-O-1)(2)Ln[(2-OCH3-C6H4NH)(2-OCH3-C6H4NH2)] (6), was isolated by protonolysis of 4 with 2-OCH3-C6H4NH2. All the complexes were structurally characterized by X-ray single crystal determination.

  DOI：

  10.1021/ic200091s
• 作为产物：
  描述：

  四氢呋喃 、 [Yb(OC6H2-4-Me-2,6-(t-Bu)2)3(N,N'-diisopropylcarbodiimide)] 以 四氢呋喃 为溶剂， 生成 Yb(O[2,6-di-tert-butyl-4-(methyl)C₆H₂])₃(tetrahydrofuran)₂
  参考文献：
  名称：

  Activation of Carbodiimide and Transformation with Amine to Guanidinate Group by Ln(OAr)₃(THF)₂ (Ln: Lanthanide and Yttrium) and Ln(OAr)₃(THF)₂ as a Novel Precatalyst for Addition of Amines to Carbodiimides: Influence of Aryloxide Group

  摘要：

  Reaction of Ln(OAr1)(3)(THF)(2) (Ar-1 = [2,6-(Bu-t)(2)-4-MeC6H2] with carbodiimides (RNCNR) in toluene afforded the RNCNR coordinated complexes ((ArO)-O-1)(3)Ln(NCNR) (R = Pr-i (isopropyl), Ln = Y (1) and Yb (2); R = Cy (cyclohexyl), Ln = Y (3)) in high yields. Treatment of 1 and 2, with 4-chloroaniline, respectively, at a molar ratio of 1:1 yielded the corresponding monoguanidinate complex ((ArO)-O-1)(2)Y[(4-Cl-C6H4N)C((NHPr)-Pr-i) (NPr)-Pr-i](THF) (4) and ((ArO)-O-1)(2)Yb[(4-Cl-C6H4N)C((NHPr)-Pr-i)(NPr)-Pr-i] (THF) (5). Complexes 4 and 5 can be prepared by the reaction of Ln(OAr1)(3)(THF)(2) with RNCNR and amine in toluene at a 1:1:1 molar ratio in high yield directly. A remarkable influence of the aryloxide ligand on this transformation was observed. The similar transformation using the less bulky yttrium complexes Y(OAr2)(3)(THF)(2) (Ar-2 = [2,6-(Pr-i)(2)C6H3]) or Y(OAr3)(3)(THF)(2) (Ar-3 = [2,6-Me2C6H3]) did not occur. Complexes Ln(OAr1)(3)(THF)(2) were found to be the novel precatalysts for addition of RNCNR with amines, which represents the first example of catalytic guanylation by the lanthanide complexes with the Ln-O active group. The catalytic activity of Y(OAr1)(3)(THF)(2) was found to be the same as that of monoguanidinate complex 4, indicating 4 is one of the active intermediates in the present process. The other intermediate, amide complex ((ArO)-O-1)(2)Ln[(2-OCH3-C6H4NH)(2-OCH3-C6H4NH2)] (6), was isolated by protonolysis of 4 with 2-OCH3-C6H4NH2. All the complexes were structurally characterized by X-ray single crystal determination.

  DOI：

  10.1021/ic200091s
• 作为试剂：
  描述：

  4-氯查耳酮 、 二乙基亚磷酸氢酯 在 Yb(O[2,6-di-tert-butyl-4-(methyl)C₆H₂])₃(tetrahydrofuran)₂ 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以90%的产率得到diethyl (1-(4-chlorophenyl)-3-oxo-3-phenylpropyl)phosphonate
  参考文献：
  名称：

  镧系元素催化亚磷酸二乙酯选择性加成到查耳酮

  摘要：

  在温和条件下实现了镧系元素催化的亚磷酸二乙酯与查耳酮的加成。该反应使用不同的催化剂表现出良好的产物选择性。Yb(OAr)3(THF)2催化的反应以高产率获得γ-氧代膦酸酯，而[(Me3Si)2N]3La(μ-Cl)Li(THF)3催化的反应得到1,2-氧代膦酸酯-5-膦酸盐作为主要产品，收率适中。该方法为具有生物学意义的相应有机磷化合物提供了简便实用的方法。

  DOI：

  10.1002/hc.21099

文献信息

• Phenylene-bridged β-Ketoiminate Dilanthanide Aryloxides: Synthesis, Structure, and Catalytic Activity for Addition of Amines to Carbodiimides
  作者：Yubiao Hong、Yu Zheng、Mingqiang Xue、Yingming Yao、Yong Zhang、Qi Shen

  DOI：10.1002/zaac.201500047

  日期：2015.6

  tetrahydrofuran) in a 1:2 molar ratio in THF, after workup, to give the corresponding dilanthanide aryloxides L[Ln(OAr)2(THF)]2 [Ln = Yb (2), Y (3), Sm (4), Nd (5), La (6)] in high isolated yields. Compound 1 and complexes 2–6 were fully characterized, including X-ray crystal structure analyses for complexes 2, 3, 5, and 6. Complexes 2–6 can be used as efficient pre-catalysts for catalytic addition of amines

  介绍了一系列由对亚苯基桥连的双（β-酮亚胺酸）配体稳定的双金属镧系元素芳基氧化物的合成和反应性。1,4-二氨基苯与乙酰丙酮以1:2.5摩尔比在无水乙醇中反应以高产率得到化合物1,4-双(4-亚氨基-2-戊酮)苯(1)(LH2)。化合物 1 与 (ArO)3Ln(THF)2（ArO = 2,6-tBu2-4-MeC6H2O，THF = 四氢呋喃）在 THF 中以 1:2 的摩尔比反应，后处理，得到相应的二镧系芳基氧化物 L[ Ln(OAr)2(THF)]2 [Ln = Yb (2), Y (3), Sm (4), Nd (5), La (6)] 分离率高。化合物 1 和配合物 2-6 得到了充分表征，包括对配合物 2、3、5 和 6 的 X 射线晶体结构分析。配合物 2-6 可用作将胺催化加成到碳二亚胺的有效预催化剂，随着La (6) < Nd (5) ≈ Sm (4) < Y (3) ≈ Yb
• Activation of Carbodiimide and Transformation with Amine to Guanidinate Group by Ln(OAr)₃(THF)₂ (Ln: Lanthanide and Yttrium) and Ln(OAr)₃(THF)₂ as a Novel Precatalyst for Addition of Amines to Carbodiimides: Influence of Aryloxide Group
  作者：Yang Cao、Zhu Du、Wenbo Li、Junmei Li、Yong Zhang、Fan Xu、Qi Shen

  DOI：10.1021/ic200091s

  日期：2011.4.18

  Reaction of Ln(OAr1)(3)(THF)(2) (Ar-1 = [2,6-(Bu-t)(2)-4-MeC6H2] with carbodiimides (RNCNR) in toluene afforded the RNCNR coordinated complexes ((ArO)-O-1)(3)Ln(NCNR) (R = Pr-i (isopropyl), Ln = Y (1) and Yb (2); R = Cy (cyclohexyl), Ln = Y (3)) in high yields. Treatment of 1 and 2, with 4-chloroaniline, respectively, at a molar ratio of 1:1 yielded the corresponding monoguanidinate complex ((ArO)-O-1)(2)Y[(4-Cl-C6H4N)C((NHPr)-Pr-i) (NPr)-Pr-i](THF) (4) and ((ArO)-O-1)(2)Yb[(4-Cl-C6H4N)C((NHPr)-Pr-i)(NPr)-Pr-i] (THF) (5). Complexes 4 and 5 can be prepared by the reaction of Ln(OAr1)(3)(THF)(2) with RNCNR and amine in toluene at a 1:1:1 molar ratio in high yield directly. A remarkable influence of the aryloxide ligand on this transformation was observed. The similar transformation using the less bulky yttrium complexes Y(OAr2)(3)(THF)(2) (Ar-2 = [2,6-(Pr-i)(2)C6H3]) or Y(OAr3)(3)(THF)(2) (Ar-3 = [2,6-Me2C6H3]) did not occur. Complexes Ln(OAr1)(3)(THF)(2) were found to be the novel precatalysts for addition of RNCNR with amines, which represents the first example of catalytic guanylation by the lanthanide complexes with the Ln-O active group. The catalytic activity of Y(OAr1)(3)(THF)(2) was found to be the same as that of monoguanidinate complex 4, indicating 4 is one of the active intermediates in the present process. The other intermediate, amide complex ((ArO)-O-1)(2)Ln[(2-OCH3-C6H4NH)(2-OCH3-C6H4NH2)] (6), was isolated by protonolysis of 4 with 2-OCH3-C6H4NH2. All the complexes were structurally characterized by X-ray single crystal determination.