sodium;N-[cyclopenta-2,4-dien-1-yl(dimethylamino)boranyl]-N-methylmethanamine;oxolane | 172660-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: sodium;N-[cyclopenta-2,4-dien-1-yl(dimethylamino)boranyl]-N-methylmethanamine;oxolane
• CAS: 172660-01-4
• 化学式: C₁₃H₂₄BN₂NaO
• 分子量: 258.147
• InChiKey: LYWZGGWBQFIMBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.98
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  15.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氢呋喃 、 sodium [bis(dimethylamino)boryl]cyclopentadienide 以 四氢呋喃 为溶剂， 生成 sodium;N-[cyclopenta-2,4-dien-1-yl(dimethylamino)boranyl]-N-methylmethanamine;oxolane
  参考文献：
  名称：

  Borylcyclopentadienides

  摘要：

  The cyclopentadienylboranes C(5)H(5)BR(2) 1-4 (R = NMe(2), 1/2(OCMe(2))(2), Pr-i, Me) are synthesized from alkali metal cyclopentadienides MCp (M = Li, Na) and BCl(NMe(2))(2), ClB (OCMe(2))(2), BClPr2i, and BBrMe(2), respectively. Compound 1 reacts with lithium dialkylamides (LiNMe(2), LDA, LiTMP) in THF or with elemental sodium to give the salts M[C5H5B(NMe(2))(2)] [M(5) with M = Li, Na]. Compounds 2 and 3 are metalated by LiTMP, and compounds 3 and 4 by cyclopentadienides MCp (M = Li, Na) to give borylcyclopentadienides or boratafulvenes M[C(5)H(5)BR(2)] M(6)-M(8) (R = 1/2(OCMe(2))(2), Pr-i, Me). Estimated (NMR) room temperature equilibrium constants for the systems 1-4/LiCp in THF are 0.5, 4, >300, and >300, respectively; they show that dialkylboryl substituents stabilize cyclopentadienide ions markedly. The triclinic THF solvate Na(THF)(5) (=10) forms an approximately trigonal helix with alternating Na(THF)(+) and anion units, while the tetragonal tetrahydropyran solvate Na(THP)(5) (=11) forms a tetragonal helix. The monoclinic solvate Li(12-crown-4)-(6) (=12) is molecular, and the orthorhombic Na(THP)(2)(8) (=13) displays a chain structure. The B-C1 distances [154.5(2) for 11, 148.8(8) for 12, and 150.8(4) pm for 13], lengthened C1-C2/C1-C5 distances (av) (142.5 for 11, 142.1 for 12, and 143.6 pm for 13), slightly lengthened C3-C4 distances (140.0 for 11, 141.1 for 12, and 143.5 pm for 13), and shortened C2-C3/C4-C5 distances (av) (140.3 for 11, 137.3 for 12, and 137.9 pm for 13) are caused by pi interactions (11 < 12, 13) between the C-5 ring and the boryl function. These interactions are weak in the case of the B(NMe(2))(2) group and quite marked for the B(OCMe(2))(2) and BMe(2) groups.

  DOI：

  10.1021/om950420a