(1-indenyl)dimethylborane | 220924-72-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: (1-indenyl)dimethylborane
• 英文别名: 1H-inden-1-yl(dimethyl)borane
• CAS: 220924-72-1
• 化学式: C₁₁H₁₃B
• 分子量: 156.035
• InChiKey: JLEPPJGEHZPTJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (1-indenyl)dimethylborane 、 2,2,6,6-tetramethylpiperidinyl-lithium 以 四氢呋喃 为溶剂， 以65%的产率得到lithium [1-(dimethylboryl)indenide]
  参考文献：
  名称：

  Synthesis of borylindenides. Complexes with iron and rhenium moieties

  摘要：

  Borylation of lithium indenide with BBrMe2 gives the allylic 1-indenyl derivative (1-Ind)BMe2 (1c) together with the bis-allylic connected species (1-Ind)(2)BMe (3) and with (BClPr2)-Pr-i, the allylic 1-indenyl (1-Ind)(BPr2)-Pr-i (1d); the latter, with Et3N or Py added, rearranges to the vinylic 3-indenyl isomer (3-Ind)(BPr)-Pr-i, (2d). The disubstituted indene C(9)H(6)Ind(SiMe3)B(O2C2Me4) (5) was prepared from Li[C9H6B(O2C2Me4)] (4b) and Me3SiCl. Both (1-Ind)BMe2 and (1-Ind)(BPr2)-Pr-i readily undergo metalation when treated with LiTMP or LiInd to give purr 1-borylindenides Li(C9H6BMe2) (4c) and Li((C9H6BPr2)-Pr-i) (4d). A barrier to internal rotation for the BMe2 group of 4c of Delta G double dagger = 65.4 +/- 2.3 kJ mol(-1) was deduced from variable temperature H-1-NMR spectra. C-13-NMR spectra of the lithium salts Li[C9H6B(NMe2)(2)] (4a), 4b, 4c and 4d display a deshielding of the carbon atoms of the Cp ring according to 4a < 4b <4c, 4d. The salts 4a and 4b were used to prepare the complexes Cp*Fe[C9H6B(NMe2)(2)] (8), Cp*Fe[C9H6B(O2C2Me4)] (9), Fe[C9H6B(O2C2Me4)](2) (10) and Re(CO)(3)[C9H6B(O2C2Me4)] (11), characterized by spectroscopic methods (H-1-, C-13-, B-11-NMR) and mass spectrometry. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00964-4
• 作为产物：
  描述：

  二甲基溴化硼 、 indenyllithium 以 正己烷 为溶剂， 以40%的产率得到(1-indenyl)dimethylborane
  参考文献：
  名称：

  Synthesis of borylindenides. Complexes with iron and rhenium moieties

  摘要：

  Borylation of lithium indenide with BBrMe2 gives the allylic 1-indenyl derivative (1-Ind)BMe2 (1c) together with the bis-allylic connected species (1-Ind)(2)BMe (3) and with (BClPr2)-Pr-i, the allylic 1-indenyl (1-Ind)(BPr2)-Pr-i (1d); the latter, with Et3N or Py added, rearranges to the vinylic 3-indenyl isomer (3-Ind)(BPr)-Pr-i, (2d). The disubstituted indene C(9)H(6)Ind(SiMe3)B(O2C2Me4) (5) was prepared from Li[C9H6B(O2C2Me4)] (4b) and Me3SiCl. Both (1-Ind)BMe2 and (1-Ind)(BPr2)-Pr-i readily undergo metalation when treated with LiTMP or LiInd to give purr 1-borylindenides Li(C9H6BMe2) (4c) and Li((C9H6BPr2)-Pr-i) (4d). A barrier to internal rotation for the BMe2 group of 4c of Delta G double dagger = 65.4 +/- 2.3 kJ mol(-1) was deduced from variable temperature H-1-NMR spectra. C-13-NMR spectra of the lithium salts Li[C9H6B(NMe2)(2)] (4a), 4b, 4c and 4d display a deshielding of the carbon atoms of the Cp ring according to 4a < 4b <4c, 4d. The salts 4a and 4b were used to prepare the complexes Cp*Fe[C9H6B(NMe2)(2)] (8), Cp*Fe[C9H6B(O2C2Me4)] (9), Fe[C9H6B(O2C2Me4)](2) (10) and Re(CO)(3)[C9H6B(O2C2Me4)] (11), characterized by spectroscopic methods (H-1-, C-13-, B-11-NMR) and mass spectrometry. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00964-4

文献信息

• Synthesis of borylindenides. Complexes with iron and rhenium moieties
  作者：Estelle Barday、Bernard Frange、Bernard Hanquet、Gerhard E. Herberich

  DOI：10.1016/s0022-328x(98)00964-4

  日期：1999.1

  Borylation of lithium indenide with BBrMe2 gives the allylic 1-indenyl derivative (1-Ind)BMe2 (1c) together with the bis-allylic connected species (1-Ind)(2)BMe (3) and with (BClPr2)-Pr-i, the allylic 1-indenyl (1-Ind)(BPr2)-Pr-i (1d); the latter, with Et3N or Py added, rearranges to the vinylic 3-indenyl isomer (3-Ind)(BPr)-Pr-i, (2d). The disubstituted indene C(9)H(6)Ind(SiMe3)B(O2C2Me4) (5) was prepared from Li[C9H6B(O2C2Me4)] (4b) and Me3SiCl. Both (1-Ind)BMe2 and (1-Ind)(BPr2)-Pr-i readily undergo metalation when treated with LiTMP or LiInd to give purr 1-borylindenides Li(C9H6BMe2) (4c) and Li((C9H6BPr2)-Pr-i) (4d). A barrier to internal rotation for the BMe2 group of 4c of Delta G double dagger = 65.4 +/- 2.3 kJ mol(-1) was deduced from variable temperature H-1-NMR spectra. C-13-NMR spectra of the lithium salts Li[C9H6B(NMe2)(2)] (4a), 4b, 4c and 4d display a deshielding of the carbon atoms of the Cp ring according to 4a < 4b <4c, 4d. The salts 4a and 4b were used to prepare the complexes Cp*Fe[C9H6B(NMe2)(2)] (8), Cp*Fe[C9H6B(O2C2Me4)] (9), Fe[C9H6B(O2C2Me4)](2) (10) and Re(CO)(3)[C9H6B(O2C2Me4)] (11), characterized by spectroscopic methods (H-1-, C-13-, B-11-NMR) and mass spectrometry. (C) 1999 Elsevier Science S.A. All rights reserved.