(4R)-2-甲基-4,5,5-三苯基-1,3,2-恶唑硼烷 | 155268-88-5

• 物质功能分类: 化学试剂 - 有机试剂 - 硼烷
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (4R)-2-甲基-4,5,5-三苯基-1,3,2-恶唑硼烷
• 英文名称: (4R)-2-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine
• 英文别名: (R)-B-methyl-4,5,5-triphenyl-1,3,2-oxazaborolidine；(R)-BMTO
• CAS: 155268-88-5
• 化学式: C₂₁H₂₀BNO
• 分子量: 313.207
• InChiKey: LDLRZFBSMOWZOS-HXUWFJFHSA-N

物化性质

• 沸点：
  405.3±55.0 °C(Predicted)
• 密度：
  1.13

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基环三硼氧烷 、 (R)-(+)-2-amino-1,1,2-triphenylethanol 以 甲苯 为溶剂， 反应 1.0h， 生成 (4R)-2-甲基-4,5,5-三苯基-1,3,2-恶唑硼烷
  参考文献：
  名称：

  A Total Synthesis of Galbonolide B

  摘要：

  [Graphics]An ester enolate rearrangement/silicon mediated fragmentation cascade was used to convert 7 and 8 into the alcohol 9. The alcohol 9 was converted into the allylic alcohol 12 and then to the ester 14. A further ester enolate rearrangement furnished the stereochemical identity of galbonolide B 1. Base mediated macrocyclization of the acetate ester 16 followed by base mediated alkylation and acetal deprotection gave galbonolide B 1.

  DOI：

  10.1021/jo701509r
• 作为试剂：
  描述：

  (S)-4-(tert-butoxycarbonylamino)-5-phenyl-1-trimethylsilylpent-1-yn-3-one 在 (4R)-2-甲基-4,5,5-三苯基-1,3,2-恶唑硼烷 、 dimethyl sulfide borane 、 bis(cyclohexanyl)borane 作用下， 以 四氢呋喃 为溶剂， 生成 2,4,5-三脱氧-4-[[(1,1-二甲基乙氧基)羰基]氨基]-5-苯基-L-苏-戊糖酸
  参考文献：
  名称：

  A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones

  摘要：

  The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00905-4

文献信息

• A Total Synthesis of Galbonolide B
  作者：Philip J. Parsons、Lewis Pennicott、James Eshelby、Matthias Goessman、Adrian Highton、Peter Hitchcock

  DOI：10.1021/jo701509r

  日期：2007.11.1

  [Graphics]An ester enolate rearrangement/silicon mediated fragmentation cascade was used to convert 7 and 8 into the alcohol 9. The alcohol 9 was converted into the allylic alcohol 12 and then to the ester 14. A further ester enolate rearrangement furnished the stereochemical identity of galbonolide B 1. Base mediated macrocyclization of the acetate ester 16 followed by base mediated alkylation and acetal deprotection gave galbonolide B 1.