diisopropyl tert-butylboronate | 124287-18-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 英文名称: diisopropyl tert-butylboronate
• 英文别名: isobutyldiisopropoxyborane；tert-butyldiisopropoxyborane；tert-butyl-di(propan-2-yloxy)borane
• CAS: 124287-18-9
• 化学式: C₁₀H₂₃BO₂
• 分子量: 186.102
• InChiKey: JQJCXNSIBLZQSL-UHFFFAOYSA-N

物化性质

• 沸点：
  157.3±9.0 °C(Predicted)
• 密度：
  0.811±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  diisopropyl tert-butylboronate 在 叔丁基锂 作用下， 以 乙醚 为溶剂， 以73%的产率得到tert-butylmethylisopropoxyborane
  参考文献：
  名称：

  Brown, Herbert C.; Srebnik, Morris; Cole, Thomas E., Organometallics, 1986, vol. 5, # 11, p. 2300 - 2303

  摘要：

  DOI：
• 作为产物：
  描述：

  硼酸三异丙酯 在 盐酸 、 叔丁基锂 作用下， 以 乙醚 为溶剂， 以68%的产率得到diisopropyl tert-butylboronate
  参考文献：
  名称：

  有机oboranes。31.由有机锂试剂和选定的三烷氧基硼烷简单制备硼酸酯

  摘要：

  DOI：

  10.1021/om50004a009

文献信息

• Total synthesis of apratoxin A and B using Matteson's homologation approach
  作者：Oliver Andler、Uli Kazmaier

  DOI：10.1039/d1ob00713k

  日期：——

  Apratoxin A and B, two members of an interesting class of marine cyclodepsipeptides are synthesized in a straightforward manner via Matteson homologation. Starting from a chiral boronic ester, the polyketide fragment of the apratoxins was obtained via five successive homologation steps in an overall yield of 27% and very good diastereoselectivity. This approach is highly flexible and should allow modification

  Apratoxin A 和 B 是一类有趣的海洋环缩肽的两个成员，通过Matteson 同源化以简单的方式合成。从手性硼酸酯开始，通过五个连续的同源化步骤获得了阿普拉毒素的聚酮化合物片段，总产率为 27%，非对映选择性非常好。这种方法非常灵活，也应该允许对这部分天然产物进行修饰，而以前的修饰主要是在肽片段中进行的。
• Process for lithium mono- and diorganylborohydrides
  申请人：Aldrich-Boranes, Inc.

  公开号：US04772751A1

  公开（公告）日：1988-09-20

  Improved processes for liberating boronic, RB(OR').sub.2, and borinic, RR'BOR', esters from their "ate" complexes, free of alcohol are provided. Pyrolysis of lithium organylborates LiRB(OR').sub.3 and LiRR'BOR', wherein R is an organyl group and R' is straight or branched-chain lower alkyl, directly yields the relatively volatile boronic and borinic esters in high purity, leaving behind a residue of lithium alkoxide. Treatment of the lithium organylborates with an appropriate acid halide cleanly liberates either volatile or non-volatile boronic or borinic esters, readily separated from the lower alkyl ester produced as a by-product. The novel compound lithium dimethylborohydride is also provided.

  提供了从其“ate”络合物中解放出无醇的硼酸酯，RB（OR'）2和硼烷酯，RR'BOR'的改进过程。锂有机硼酸盐LiRB（OR'）3和LiRR'BOR'的热解，其中R是有机基团，R'是直链或支链低级烷基，直接产生相对挥发性的高纯度硼酸酯和硼烷酯，留下锂烷氧化物残留物。用适当的酸卤处理锂有机硼酸盐可以干净地释放出挥发性或非挥发性的硼酸酯或硼烷酯，并容易与产生的低级烷基酯副产物分离。还提供了新型化合物锂二甲基硼氢化物。
• Improved process for producing pure boronic and borinic esters
  申请人：Aldrich-Boranes, Inc.

  公开号：US04870177A1

  公开（公告）日：1989-09-26

  Improved processes for liberating boronic, RB(OR').sub.2, and borinic, RR'BOR', esters from their "ate" complexes, free of alcohol are provided. Pyrolysis of lithium organylborates LiRB(OR').sub.3 and LiRR'BOR', wherein R is an organyl group and R' is straight or branched-chain lower alkyl, directly yields the relatively volatile boronic and borinic esters in high purity, leaving behind a residue of lithium alkoxide. Treatment of the lithium organylborates with an appropriate acid halide cleanly liberates either volatile or non-volatile boronic or borinic esters, readily separated from the lower alkyl ester produced as a by-product. The novel compound lithium dimethylborohydride is also provided.

  提供了从它们的“ate”配合物中解放出无醇的硼酸酯，RB（OR'）2和硼烷酸酯，RR'BOR'的改进过程。热解锂有机硼酸盐LiRB（OR'）3和LiRR'BOR'，其中R是有机基团，R'是直链或支链低碳链烷基，直接产生相对挥发性的高纯度硼酸酯和硼烷酸酯，留下锂烷氧化物的残留物。用适当的酸卤处理锂有机硼酸盐可以干净地解放出挥发性或非挥发性的硼酸酯或硼烷酸酯，容易与产生的低碳链酯副产物分离。还提供了新型化合物锂二甲基硼氢化物。
• Process for synthesizing lithium mono- and diorganylborohydrides
  申请人：Aldrich-Boranes, Inc.

  公开号：US04870212A1

  公开（公告）日：1989-09-26

  Improved processes for liberating boronic, RB(OR').sub.2, and borinic, RR'BOR', esters from their "ate" complexes, free of alcohol are provided. Pyrolysis of lithium organylborates LiRB(OR').sub.3 and LiRR'BOR', wherein R is an organyl group and R' is straight or branched-chain lower alkyl, directly yields the relatively volatile boronic and borinic esters in high purity, leaving behind a residue of lithium alkoxide. Treatment of the lithium organylborates with an appropriate acid halide cleanly liberates either volatile or non-volatile boronic or borinic esters, readily separated from the lower alkyl ester produced as a by-product. The novel compound lithium dimethylborohydride is also provided.

  提供了一种改进的过程，用于从其“ate”络合物中解放出不含醇的硼酸酯、RB（OR'）2和硼烷酸酯、RR'BOR'。锂有机硼酸盐LiRB（OR'）3和LiRR'BOR'的热解，其中R是有机基团，R'是直链或支链低级烷基，直接产生相对挥发性的高纯度硼酸酯和硼烷酸酯，留下一定量的锂烷氧化物残留物。用适当的酸卤化物处理锂有机硼酸盐可以干净地释放出易挥发或不易挥发的硼酸酯或硼烷酸酯，可以很容易地与产生的低级烷酸酯副产物分离。还提供了一种新的化合物锂二甲基硼氢化物。
• Organoboranes. 56. Systematic study of the reactions of 1-alkenylboronic esters with representative organolithium and Grignard reagents to provide an efficient, selective synthesis of organyl-1-alkenylborinic esters
  作者：Herbert C. Brown、Nagarajan Vasumathi、Navalkishore N. Joshi

  DOI：10.1021/om00028a021

  日期：1993.4

  A selective reaction of the ''ate'' complexes formed with 1-alkenylboronic esters and organolithium or Grignard reagents, by treatment with either Bronsted or Lewis acids at -78-degrees-C to give the corresponding organylalkenylborinic esters, is explored in this study. This systematic, detailed study reveals that the nature of the alkoxy group on boron, the nature and the amount of the alkyllithium or Grignard reagent used, the solvent, the reaction temperature, and the nature and amount of the acid used all play significant roles in influencing both the yield and the selectivity achieved for the formation of the desired organylalkenylborinates. Optimized procedures for the syntheses of representative organylalkenylborinic esters in high yield are summarized.