Bis(acetoxy)diethyldiboroxan | 111849-46-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Bis(acetoxy)diethyldiboroxan
• 英文别名: 1,3-acetoxy-1,3-diethyldiboroxane；1,3-diacetoxy-1,3-diethyl-1,3-diboroxane；1,5-diethyl-3,7-dimethyl-4,8,9-trioxa-2,6-dioxonia-1,5-diborabicyclo[3.3.1]nona-2,6-diene；(EtB)2(μ-O)(μ-O,O'-O2CCH3)2；1,5-Diethyl-3,7-dimethyl-4,8,9-trioxa-2,6-dioxonia-1,5-diboranuidabicyclo[3.3.1]nona-2,6-diene；1,5-diethyl-3,7-dimethyl-4,8,9-trioxa-2,6-dioxonia-1,5-diboranuidabicyclo[3.3.1]nona-2,6-diene
• CAS: 111849-46-8
• 化学式: C₈H₁₆B₂O₅
• 分子量: 213.834
• InChiKey: MUJXALVEUWJDAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  triethylboroxine 、 Bis(acetoxy)diethyldiboroxan 以 氘代甲苯 为溶剂， 生成 1,5-diethyl-3,7-dimethyl-4,8,9-trioxa-2,6-dioxonia-1,5-diborata{3.3.1}nona-2,6-diene
  参考文献：
  名称：

  Koester, Roland; Sporzynski, Andrzej; Schuessler, Wilhelm, Chemische Berichte, 1994, vol. 127, # 7, p. 1191 - 1200

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三乙基环硼氧烷 在 乙酸酐 作用下， 以 乙酸酐 为溶剂， 以87%的产率得到Bis(acetoxy)diethyldiboroxan
  参考文献：
  名称：

  New 1,3-diacyloxy-1,3-diethyldiboroxanes. Equilibrium of chelate ring formation

  摘要：

  New 1,3-diacyloxy-1,3-diethyldiboroxanes [Et(RCOO)B]2O containing electron-withdrawing atoms in the acyloxy group were synthesized. On the basis of B-11 NMR spectra the equilibrium between the forms containing tetra- and tricoordinated boron atoms is proposed. This equilibrium is influenced by the kind of acyloxy group and by the temperature.

  DOI：

  10.1016/0022-328x(93)80093-q

文献信息

• Protodeborylation of Triorganoboranes
  作者：Bernd Wrackmeyer、Ezzat Khan、Rhett Kempe

  DOI：10.1515/znb-2008-0308

  日期：2008.3.1

  Protodeborylation of triorganoboranes, usually carried out under mild reaction conditions using an excess of acetic acid, affords 1,5-dialkyl-3,7-dimethyl-4,8,9-trioxa-2,6-dioxonia-1,5-diboratabicyclo [3.3.1]nona-2,6-dienes OB(R)OC(Me)OB(R)OC(Me)O [1 (R = Et), 2 (R = cyclooctyl)]. Acetoxy(dialkyl) boranes and di(acetoxy)alkylboranes were not formed in an appreciable amount. Compounds 1 and 2 were characterized by NMR spectroscopy (¹H, ¹¹B, ¹³C NMR) in solution, the molecular structure of 2 was determined by X-ray analysis. The gas-phase geometry of 1 was optimized by calculations [B3LYP/6-311+G(d, p) level of theory], and its NMR parameters were also calculated at the same level of theory.

  三有机硼烷的原始脱硼反应通常在温和的反应条件下使用过量的乙酸进行，得到1,5-二烷基-3,7-二甲基-4,8,9-三氧杂-2,6-二氧杂-1,5-二硼杂双环[3.3.1]壬-2,6-二烯OB(R)OC(Me)OB(R)OC(Me)O [1 (R = Et), 2 (R = 环辛基)]。乙酰氧基(二烷基)硼烷和双(乙酰氧基)烷基硼烷的形成量不多。化合物1和2通过溶液中的NMR光谱（1H、11B、13C NMR）进行了表征，2的分子结构通过X射线分析确定。1的气相几何构型通过计算进行了优化[B3LYP/6-311+G(d, p)理论水平]，其NMR参数也在相同水平的理论下计算。
• Synthesis and Molecular Structure of Silole Derivatives Bearing Functional Groups on Silicon: 1,1‐Organoboration of Dialkynylsilanes
  作者：Ezzat Khan、Stefan Bayer、Rhett Kempe、Bernd Wrackmeyer

  DOI：10.1002/ejic.200900697

  日期：2009.10

  bearing Si–H or SiCl functions in addition to the alkynyl groups react with an excess of triethylborane after heating at 100–110 °C for several days via slow intermolecular 1,1-ethylboration followed by fast intramolecular 1,1-vinylboration to give Si-functional substituted siloles. Similarly, the reactions with 9-ethyl-9-borabicyclo[3.3.1]nonane afford polycyclic compounds containing the silole ring. Protodeborylaton

  在 100-110 °C 下加热数天后，除炔基外还带有 Si-H 或 SiCl 官能团的各种二炔基硅烷通过缓慢的分子间 1,1-乙基硼化和快速的分子内 1,1-乙烯基硼化反应生成得到 Si 功能取代的硅酮。类似地，与 9-乙基-9-硼双环 [3.3.1] 壬烷的反应得到含有噻咯环的多环化合物。具有过量乙酸的原脱硼酸导致同时取代 BEt2 和 Si-H 官能团，得到 1-乙酰氧基甲硅烷。所有新硅醇都通过溶液中的 NMR 光谱（1H、11B、13C、29Si NMR）进行表征，对于多环硅醇衍生物的一个例子，其分子结构是通过 X 射线分析确定的。（© Wiley-VCH Verlag GmbH & Co . KGaA, 69451 德国魏因海姆, 2009)
• Syntheses of 1,1-Organo-substituted Silole Derivatives. 1,1-Ethylboration, 1,1-Vinylboration and Protodeborylation
  作者：Ezzat Khan、Stefan Bayer、Bernd Wrackmeyer

  DOI：10.1515/znb-2009-0902

  日期：2009.9.1

  1,1-Organoboration of dialkyn-1-ylsilanes using triethylborane, BEt₃, and 9-ethyl-9-borabicyclo [3.3.1]nonane, Et-9-BBN, was carried out at elevated temperatures, 100 - 120 °C. These reactions afforded selectively silole derivatives bearing the dialkylboryl group in 3-position. The siloles are formed via intermolecular 1,1-alkylboration, followed by intramolecular 1,1-vinylboration. Two examples of boryl-substituted siloles were treated with an excess of acetic acid at ambient temperature to afford the respective protodeborylated compounds. All new compounds were characterized in solution by multinuclear magnetic resonance spectroscopy (¹H, ¹³C, ¹¹B and ²⁹Si NMR).

  使用三乙基硼、BEt3和9-乙基-9-硼杂双环[3.3.1]非烷（Et-9-BBN）在高温（100-120°C）下对双炔基-1-基硅烷进行了1,1-有机硼化反应。这些反应选择性地形成了3-位带有二烷基硼基的硅杂环烃衍生物。硅杂环烃是通过分子间1,1-烷基硼化反应，随后是分子内1,1-烯基硼化反应形成的。两个硼取代的硅杂环烃的例子在室温下过量使用乙酸处理，形成了相应的脱硼化合物。所有新化合物均通过多核磁共振光谱（1H，13C，11B和29Si NMR）在溶液中进行了表征。
• Koester, Roland; Seidel, Guenter; Boese, Roland, Chemische Berichte, 1988, vol. 121, p. 597 - 616
  作者：Koester, Roland、Seidel, Guenter、Boese, Roland、Wrackmeyer, Bernd

  DOI：——

  日期：——
• Koester, Roland; Seidel, Guenter; Boese, Roland, Chemische Berichte, 1988, vol. 121, p. 709 - 722
  作者：Koester, Roland、Seidel, Guenter、Boese, Roland、Wrackmeyer, Bernd

  DOI：——

  日期：——