dibutoxyborane | 22694-36-6

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: dibutoxyborane
• 英文别名: HB(n-BuO)2
• CAS: 22694-36-6
• 化学式: C₈H₁₉BO₂
• 分子量: 158.049
• InChiKey: FGMZCSZIFQZIKC-UHFFFAOYSA-N

物化性质

• 沸点：
  187.1±9.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  11.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  dibutoxyborane 、 tri-tert-butylphosphoranimine 以 四氢呋喃 、 甲苯 为溶剂， 以95%的产率得到Tritert-butyl(dibutoxyboranylimino)-lambda5-phosphane
  参考文献：
  名称：

  Boron and Aluminum Complexes of Sterically Demanding Phosphinimines and Phosphinimides

  摘要：

  Reactions of sterically demanding phosphinimines R3PNH [R = i-Pr (1), t-Bu (2)] were examined. Reactions with B(C6F5)(3) formed the adducts (R3PNH)B(C6F5)(3) [R = i-Pr (3), t-Bu (4)] in high yield. On the other hand, 2 reacts with HB(OBu)(2), evolving H-2 to give t-Bu3PNB(OBu)(2) (5). The reaction of 2 equiv of 2 with BH3 center dot SMe2 affords the species (t-Bu3PN)(2)BH (6). In contrast, the reaction of n-Bu(t-Bu)(2)PNH with BH3 center dot SMe2 results in the formation of the robust adduct n-Bu(t-Bu)(2)PNH center dot BH3 (8). An alternative route to borane-phosphinimide complexes involves Me3SiCl elimination, as exemplified by the reaction of BCl2Ph with n-Bu3PNSiMe3, which gives the product n-Bu3PNBCl(Ph) (9). The corresponding reactions of the parent phosphinimines 1 and 2 with AlH3 center dot NMe2Et give the dimers [(mu-i-Pr3PN)AlH2](2) (10) and [(mu-t-Bu3PN)AlH2](2) (11). Species 11 reacts further with Me3SiO3SCF3 to provide [(mu-t-Bu3PN)AlH(OSO2CF3)](2) (12). The reaction of the lithium salt [t-Bu3PNLi](4) (13) with BCl3 proceeds smoothly to give t-Bu3PNBCl2 (14), which is readily alkylated to give t-Bu3PNBMe2 (15). Subsequent reaction of 15 with B(C6F5)(3) results in methyl abstraction and the formation of [(mu-t-Bu3PN)BMe](2)[MeB(C6F5)(3)](2) (16). The reaction of 13 in a 2:1 ratio with BCl3 gives the salt [(t-Bu3PN)(2)B]Cl (17). This species can be methylated to give (t-Bu3PN)(2)BMe (18), which undergoes subsequent reaction with [Ph3C][X] (X = [B(C6F5)(4)], [PF6]) to form the related salts [(t-Bu3PN)(2)B][B(C6F5)(4)] (19) and [(t-Bu3PN)(2)B][PF6] (20), respectively. Analogous reactions with [Ph3C][BF4] afforded [t-Bu3PNBF2](2) (21). Compounds 3, 4, 6, 8, 11, 12, 17, 19, and 21 were characterized by X-ray crystallography.

  DOI：

  10.1021/ic0700351
• 作为产物：
  描述：

  硼酸三丁酯 、 氢溴酸 在 magnesium 作用下， 生成 dibutoxyborane
  参考文献：
  名称：

  Dandegaonker, S. H.; Ingleshwar, S. P., Journal of Shivaji University, 1973, vol. 6, # 12, p. 11 - 13

  摘要：

  DOI：
• 作为试剂：
  描述：

  1-己烯 在 dibutoxyborane 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 生成 2-己醇 、 正己醇
  参考文献：
  名称：

  Lithium triethylborohydride-promoted hydroboration of alkenes with dialkoxyboranes

  摘要：

  在一定量的三乙基硼氢化锂（LiBEt3H）催化下，烯烃与二烷氧基硼烷的硼氢化反应明显加快，在温和的反应条件下几乎可以定量提供硼氢化产物。

  DOI：

  10.1039/c39920000051

文献信息

• Ready Preparation of Trialkoxyboranes and Dialkoxyboranes by LiBEt₃H-Promoted Reaction of BH₃in Tetrahydrofuran with Alcohols
  作者：Yuzuru Masuda、Yutaka Nunokawa、Masayuki Hoshi、Akira Arase

  DOI：10.1246/cl.1992.349

  日期：1992.3

  A catalytic amount of LiBEt3H (1%) promoted markedly the reactions of BH3 in tetrahydrofuran (THF) with stoichiometric amounts of alcohols (1:2 and 1:3) to provide corresponding trialkoxyboranes and dialkoxyboranes quantitatively under mild reaction conditions.

  催化量的 LiBEt3H (1%) 显着促进了 BH3 在四氢呋喃 (THF) 中与化学计量量的醇 (1:2 和 1:3) 的反应，以在温和的反应条件下定量提供相应的三烷氧基硼烷和二烷氧基硼烷。
• Triorganyl‐ and Diorganyloxozirconium Hydridoborates – Synthesis and Structures
  作者：Jörg Knizek、Heinrich Nöth、Martin Schmidt‐Amelunxen

  DOI：10.1002/ejic.201100548

  日期：2011.12

  The reactions of Zr(OBu)4 and Zr(OEt)4 with H3B·THF in THF led to HB(OR)2 and B(OR)3, but no zirconium tetrahydroborate [(RO)4–nZr(BH4)n] could be isolated. On the contrary, the reactions of [tBu3CO]4–nZrCln and [tBu3SiO]4–nZrCln with LiBH4 generated the tetrahydroborates [(RO)3Zr(BH4)] and [(RO)2Zr(BH4)2]. These can be used to produce by hydroborate exchange dihydridodiorganyl borates [(RO)4–nZr(H2BC8H14)n]

  Zr(OBu)4 和 Zr(OEt)4 与 H3B·THF 在 THF 中的反应导致 HB(OR)2 和 B(OR)3，但没有四氢硼酸锆 [(RO)4–nZr(BH4)n]可以隔离。相反，[tBu3CO]4-nZrCln 和 [tBu3SiO]4-nZrCln 与 LiBH4 的反应生成了四氢硼酸盐 [(RO)3Zr(BH4)] 和 [(RO)2Zr(BH4)2]。这些可用于通过硼氢化物交换来生产二氢化二有机基硼酸盐 [(RO)4–nZr(H2BC8H14)n] 和副产品。新的氢化硼酸锆的结构已通过 X 射线晶体学确定。化合物 [(tBu3CO)3Zr(H2BC8H14)] 显示出位点无序的二氢硼酸盐单元，具有极好的 Zr-H-C 相互作用，而 [(tBu3SiO)2Zr(H2BC8H14)2] 是非常对称的 (C2/c)。在大多数情况下，相应的四氢硼酸盐具有 μ31 键合的 ZrH3BH
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: B: B-Verb.13, 2.2.7, page 71 - 82
  作者：

  DOI：——

  日期：——
• Reactions of the octahydrotriborate (−1) ion with mercury salts
  作者：A. Drummond、J.H. Morris

  DOI：10.1016/s0020-1693(00)93871-4

  日期：1977.1
• Boron and Aluminum Complexes of Sterically Demanding Phosphinimines and Phosphinimides
  作者：Silke Courtenay、Denise Walsh、Sarah Hawkeswood、Pingrong Wei、Anjan Kumar Das、Douglas W. Stephan

  DOI：10.1021/ic0700351

  日期：2007.4.30

  Reactions of sterically demanding phosphinimines R3PNH [R = i-Pr (1), t-Bu (2)] were examined. Reactions with B(C6F5)(3) formed the adducts (R3PNH)B(C6F5)(3) [R = i-Pr (3), t-Bu (4)] in high yield. On the other hand, 2 reacts with HB(OBu)(2), evolving H-2 to give t-Bu3PNB(OBu)(2) (5). The reaction of 2 equiv of 2 with BH3 center dot SMe2 affords the species (t-Bu3PN)(2)BH (6). In contrast, the reaction of n-Bu(t-Bu)(2)PNH with BH3 center dot SMe2 results in the formation of the robust adduct n-Bu(t-Bu)(2)PNH center dot BH3 (8). An alternative route to borane-phosphinimide complexes involves Me3SiCl elimination, as exemplified by the reaction of BCl2Ph with n-Bu3PNSiMe3, which gives the product n-Bu3PNBCl(Ph) (9). The corresponding reactions of the parent phosphinimines 1 and 2 with AlH3 center dot NMe2Et give the dimers [(mu-i-Pr3PN)AlH2](2) (10) and [(mu-t-Bu3PN)AlH2](2) (11). Species 11 reacts further with Me3SiO3SCF3 to provide [(mu-t-Bu3PN)AlH(OSO2CF3)](2) (12). The reaction of the lithium salt [t-Bu3PNLi](4) (13) with BCl3 proceeds smoothly to give t-Bu3PNBCl2 (14), which is readily alkylated to give t-Bu3PNBMe2 (15). Subsequent reaction of 15 with B(C6F5)(3) results in methyl abstraction and the formation of [(mu-t-Bu3PN)BMe](2)[MeB(C6F5)(3)](2) (16). The reaction of 13 in a 2:1 ratio with BCl3 gives the salt [(t-Bu3PN)(2)B]Cl (17). This species can be methylated to give (t-Bu3PN)(2)BMe (18), which undergoes subsequent reaction with [Ph3C][X] (X = [B(C6F5)(4)], [PF6]) to form the related salts [(t-Bu3PN)(2)B][B(C6F5)(4)] (19) and [(t-Bu3PN)(2)B][PF6] (20), respectively. Analogous reactions with [Ph3C][BF4] afforded [t-Bu3PNBF2](2) (21). Compounds 3, 4, 6, 8, 11, 12, 17, 19, and 21 were characterized by X-ray crystallography.