(R,R)-2-butyl-4,5-dicyclohexyl-1,3,2-dioxaborolane | 159656-91-4

• 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: (R,R)-2-butyl-4,5-dicyclohexyl-1,3,2-dioxaborolane
• 英文别名: -2-methyl-4,5-dicyclohexyl-1,3,2-dioxaborolane；(4R,5R)-2-butyl-4,5-dicyclohexyl-1,3,2-dioxaborolane
• CAS: 159656-91-4
• 化学式: C₁₈H₃₃BO₂
• 分子量: 292.27
• InChiKey: GGNSYGFUWUGKAZ-QZTJIDSGSA-N

物化性质

• 沸点：
  374.6±11.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• 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：

  (R,R)-2-butyl-4,5-dicyclohexyl-1,3,2-dioxaborolane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  单锅不对称方法制备富含对映体的季立体中心亚烷基亚环丁烷

  摘要：

  通过高效和非对映选择性的一锅法将双硼同位和烯丙基硼化结合起来，合成了通常难以接近的，具有季生立体中心的对映体富集的亚烷基亚环丁烷。从可商购获得的底物开始，该方案代表了一种以优异的立体异构体比率获得手性不饱和四元环系统的简单方法。

  DOI：

  10.1021/acs.orglett.6b01432
• 作为产物：
  描述：

  2-丁基-4,4,5,5-四甲基-1,3,2-二杂氧戊硼酸 、 (1R,2R)-(-)-1,2-二环己基-1,2-乙二醇 以100%的产率得到(R,R)-2-butyl-4,5-dicyclohexyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  在配位溶剂中用四氯硅烷将三氟硼酸烷基酯转化为烷基二氯硼烷。

  摘要：

  DOI：

  10.1002/anie.200453690

文献信息

• Enantioselective Capture and Retroracemization of (1-Bromoalkyl)boronic Esters by an N-Propanoyloxazolidinone Enolate and Iodide Ion
  作者：Donald S. Matteson、Hon-Wah Man

  DOI：10.1021/jo00098a036

  日期：1994.9

  Lithium enolates of N-propanoyloxazolidinones react with (1-bromoethyl)boronic esters to form predominantly threo-2-methyl-3-borylbutanoic acid derivatives. The reaction of enantiomerically pure oxazolidinone enolate 2 with excess racemic (1-bromoethyl)boronic ester rac-3a produced a single isolable product 4a in high diastereomeric and enantiomeric purity. Iodide catalysts resulted in racemization of any excess of ent-3a back to rac-3a so that both enantiomers were utilized via 3a (hence, ''retroracemization'') in the presence of 1 equiv of 2 to produce 4a, again in high purity and yield. The (1-bromoethyl)boronic ester rac-3b underwent similar retroracemization, though less efficiently. (Haloalkyl)boronic esters of much higher or lower reactivity did not undergo useful Im an attempt to direct the reaction to produce erythro isomer, 2 was paired with (1-bromoethyl)boronic ester 10, but the predominant product remained the threo isomer. The enantiomeric composition of this threo product was subsequently called into question by the observation that (1-bromopentyl)boronic ester 13 epimerizes readily to 14 and that both 13 and 14 with the lithium enolate of tert-butyl propanoate. This result contrasts sharply to the previously reported grossly differing behaviors of diastereomeric pairs of (1-chloroalkyl)boronic esters toward Grignard reagents and provides a warning that the previously reported reactions of (1-bromoalkyl)boronic esters with carboxylic ester enolates do not necessarily lead to good enantiomeric purities.