3-(3,5-二氯苯)苯甲醛 | 860265-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(3,5-二氯苯)苯甲醛
• 英文名称: 7-Oxo-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester
• 英文别名: N-Cbz-2-azabicyclo[2.2.1]heptan-7-one；benzyl 7-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate
• CAS: 860265-68-5
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: IHWYEYKAGXDORD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(3,5-二氯苯)苯甲醛 在 sodium tetrahydroborate 作用下， 生成 (1R,4R,7R)-7-Hydroxy-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Approaches to Syn-7-Substituted 2-Azanorbornanes as Potential Nicotinic Agonists; Synthesis of syn- and anti-Isoepibatidine

  摘要：

  Coupling of N-Boc-7-bromo-2-azabicyclo[2.2.1]heptane with aryl and pyridyl boronic acids incorporates aryl and heterocyclic substituents at the 7-position and leads to a preference for syn over anti stereoisomers. Incorporation of a chloropyridyl group followed by N-deprotection gives syn-isoepibatidine. Facial selectivity in attack on 7-keto-2-azanorbornanes depends heavily on the N-protecting group leading to the first syn-7-hydroxy-2-azabicyclo[2.2.1]heptane derivative.

  DOI：

  10.1021/ol0510365
• 作为产物：
  描述：

  (1R,4R,7R)-7-Hydroxy-2-aza-bicyclo[2.2.1]heptane-2-carboxylic acid benzyl ester 生成 3-(3,5-二氯苯)苯甲醛
  参考文献：
  名称：

  Approaches to Syn-7-Substituted 2-Azanorbornanes as Potential Nicotinic Agonists; Synthesis of syn- and anti-Isoepibatidine

  摘要：

  Coupling of N-Boc-7-bromo-2-azabicyclo[2.2.1]heptane with aryl and pyridyl boronic acids incorporates aryl and heterocyclic substituents at the 7-position and leads to a preference for syn over anti stereoisomers. Incorporation of a chloropyridyl group followed by N-deprotection gives syn-isoepibatidine. Facial selectivity in attack on 7-keto-2-azanorbornanes depends heavily on the N-protecting group leading to the first syn-7-hydroxy-2-azabicyclo[2.2.1]heptane derivative.

  DOI：

  10.1021/ol0510365

文献信息

• Approaches to Syn<i>-</i>7-Substituted 2-Azanorbornanes as Potential Nicotinic Agonists; Synthesis of <i>s</i><i>yn- </i>and <i>a</i><i>nti-</i>Isoepibatidine
  作者：John R. Malpass、Sandeep Handa、Richard White

  DOI：10.1021/ol0510365

  日期：2005.6.1

  Coupling of N-Boc-7-bromo-2-azabicyclo[2.2.1]heptane with aryl and pyridyl boronic acids incorporates aryl and heterocyclic substituents at the 7-position and leads to a preference for syn over anti stereoisomers. Incorporation of a chloropyridyl group followed by N-deprotection gives syn-isoepibatidine. Facial selectivity in attack on 7-keto-2-azanorbornanes depends heavily on the N-protecting group leading to the first syn-7-hydroxy-2-azabicyclo[2.2.1]heptane derivative.