(R)-2-bromo-5-phenylpentane | 1357017-35-6

• 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: (R)-2-bromo-5-phenylpentane
• 英文别名: (r)-2-Bromo-5-phenylpentane；[(4R)-4-bromopentyl]benzene
• CAS: 1357017-35-6
• 化学式: C₁₁H₁₅Br
• 分子量: 227.144
• InChiKey: PCGYMVLAXCQBPQ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (S)-5-phenylpent-4-yn-2-ol 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 (R)-2-bromo-5-phenylpentane
  参考文献：
  名称：

  Copper(I)-Catalyzed Boryl Substitution of Unactivated Alkyl Halides

  摘要：

  Borylation of alkyl halides with diboron proceeded in the presence of a copper(I)/Xantphos catalyst and a stoichiometric amount of K(O-t-Bu) base. The boryl substitution proceeded with normal and secondary alkyl chlorides, bromides, and iodides, but alkyl sulfonates did not react. Menthyl halides afforded the corresponding borylation product with excellent diastereoselectivity, whereas (R)-2-bromo-5-phenylpentane gave a racemic product. Reaction with cyclopropylmethyl bromide resulted in ring-opening products, suggesting the reaction involves a radical pathway.

  DOI：

  10.1021/ol203413w

文献信息

• Copper(I)-Catalyzed Boryl Substitution of Unactivated Alkyl Halides
  作者：Hajime Ito、Koji Kubota

  DOI：10.1021/ol203413w

  日期：2012.2.3

  Borylation of alkyl halides with diboron proceeded in the presence of a copper(I)/Xantphos catalyst and a stoichiometric amount of K(O-t-Bu) base. The boryl substitution proceeded with normal and secondary alkyl chlorides, bromides, and iodides, but alkyl sulfonates did not react. Menthyl halides afforded the corresponding borylation product with excellent diastereoselectivity, whereas (R)-2-bromo-5-phenylpentane gave a racemic product. Reaction with cyclopropylmethyl bromide resulted in ring-opening products, suggesting the reaction involves a radical pathway.