(S)-1-(4-bromophenyl)but-3-yn-1-ol | 1276110-96-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-(4-bromophenyl)but-3-yn-1-ol
• 英文别名: (1S)-1-(4-bromophenyl)but-3-yn-1-ol
• CAS: 1276110-96-3
• 化学式: C₁₀H₉BrO
• 分子量: 225.085
• InChiKey: CFWCQNUGZLIQIC-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-bromophenyl)but-3-yn-1-ol 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-1-phenylbut-3-yn-1-ol
  参考文献：
  名称：

  Helical Chiral 2,2′-Bipyridine N- Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane

  摘要：

  A highly enantioselective synthesis of homopropargylic alcohols is achieved by using the new helical chiral 2,2'-bipyridine N-monoxide catalyst and allenyltrichlorosilane. This method can be further extended to the enantio- and regioselective propargylation of N-acylhydrazones.

  DOI：

  10.1021/ol200102c
• 作为产物：
  描述：

  allenyltrichlorosilane 、 对溴苯甲醛 在 C₃₄H₂₀N₂O 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以95%的产率得到(S)-1-(4-bromophenyl)but-3-yn-1-ol
  参考文献：
  名称：

  Helical Chiral 2,2′-Bipyridine N- Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane

  摘要：

  A highly enantioselective synthesis of homopropargylic alcohols is achieved by using the new helical chiral 2,2'-bipyridine N-monoxide catalyst and allenyltrichlorosilane. This method can be further extended to the enantio- and regioselective propargylation of N-acylhydrazones.

  DOI：

  10.1021/ol200102c

文献信息

• A facile lipase-catalyzed KR approach toward enantiomerically enriched homopropargyl alcohols
  作者：Paweł Borowiecki、Maciej Dranka

  DOI：10.1016/j.bioorg.2019.01.050

  日期：2019.12

  (E ≫ 500) furnishing both resolution products of the racemic 1-phenylbut-3-yn-1-ol in highly enantiomerically enriched form (up > 99% ee). Variable reaction parameters, such as the acyl-group donor reagent as well as solvent, were additionally screened to establish their impact on the stereochemical outcome. For optimal biocatalytic systems established with model substrate, the enzymatic transformations were

  具有炔丙基（丙-2-炔）体系的化合物是有机化学非常重要的组成部分。其中，对映体高炔丙醇（but-3-yn-1-ols）的制备构成了不对称合成的关键挑战，因此在过去的几十年中引起了合成界的极大关注。在这项工作中，已经研究了一组商业脂肪酶的催化性能，用于在动力学控制的条件下对1-苯基高炔丙基醇进行对映选择性酯交换。固定在陶瓷（Amano PS-C II）或硅藻土（Amano PS-IM）上的洋葱伯克霍尔德氏菌（BCL）的脂肪酶是最活跃和对映选择性的酶制剂（E ≫ 500）提供了高度对映体富集形式的外消旋1-苯基丁-3-炔-1-醇的两种拆分产物（大于99％ee）。另外还筛选了可变的反应参数，例如酰基供体试剂和溶剂，以确定它们对立体化学结果的影响。对于建立有模型底物的最佳生物催化系统，酶促转化扩展到了其他8种不同的对苯基取代的均丙基仲醇的制备规模KR ，从而合成了（S）醇（96-100％ee ）和
• Chiral Brønsted Acid Catalyzed Enantioselective Propargylation of Aldehydes with Allenylboronate
  作者：Leleti Rajender Reddy

  DOI：10.1021/ol300075n

  日期：2012.2.17

  A highly enantioselective chiral Brønsted acid catalyzed propargylation of aldehydes with allenylboronate is described. The reaction is shown to be practical and quite general with a broad substrate scope covering aryl, polyaryl, heteroaryl, α,β-unsaturated, and aliphatic aldehydes.

  描述了高度对映选择性的手性布朗斯台德酸与烯丙基硼酸酯的醛的炔丙基化。该反应被证明是实用的并且相当普遍，具有广泛的底物范围，包括芳基，聚芳基，杂芳基，α，β-不饱和醛基和脂族醛。
• Ligand-accelerated Enantioselective Propargylation of Aldehydes via Allenylzinc Reagents
  作者：Barry M. Trost、Ming-Yu Ngai、Guangbin Dong

  DOI：10.1021/ol200043n

  日期：2011.4.15

  An enantioselective propargylation of aldehydes using an allenylzinc reagent generated in situ via a zinc-iodine exchange reaction is described. The enantioselectivity is controlled by addition of a catalytic amount of readily accessible and highly tunable amino alcohol ligand L13. A wide range of aldehydes can be propargylated to afford valuable and versatile homopropargyl alcohols in good to excellent yields with high levels of enantiopurity.
• Helical Chiral 2,2′-Bipyridine <i>N-</i> Monoxides as Catalysts in the Enantioselective Propargylation of Aldehydes with Allenyltrichlorosilane
  作者：Jinshui Chen、Burjor Captain、Norito Takenaka

  DOI：10.1021/ol200102c

  日期：2011.4.1

  A highly enantioselective synthesis of homopropargylic alcohols is achieved by using the new helical chiral 2,2'-bipyridine N-monoxide catalyst and allenyltrichlorosilane. This method can be further extended to the enantio- and regioselective propargylation of N-acylhydrazones.