2-(3-bromo-phenyl)-2-hydroxy-3-methyl-4-phenyl-but-3-enoic acid methyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-(3-bromo-phenyl)-2-hydroxy-3-methyl-4-phenyl-but-3-enoic acid methyl ester
• 英文别名: methyl (E)-2-(3-bromophenyl)-2-hydroxy-3-methyl-4-phenylbut-3-enoate
• 化学式: C₁₈H₁₇BrO₃
• 分子量: 361.235
• InChiKey: BLNXSEPNDDMIAI-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苯基-1-丙炔 、 2-(3-溴苯基)-2-氧代乙酸甲酯 在 Ir(cod)2BARF 三苯基乙酸 、 氢气 、 2,2'-双(二苯基磷)联苯 作用下， 以 1,2-二氯乙烷 为溶剂， 80.0 ℃ 、101.32 kPa 条件下， 反应 6.0h， 以73%的产率得到2-(3-bromo-phenyl)-2-hydroxy-3-methyl-4-phenyl-but-3-enoic acid methyl ester
  参考文献：
  名称：

  Iridium-Catalyzed C−C Bond Forming Hydrogenation:  Direct Regioselective Reductive Coupling of Alkyl-Substituted Alkynes to Activated Ketones

  摘要：

  commercially available alkyl-substituted alkynes, 3-hexyne 1a and 1-phenylpropyne 1b, in the presence of alpha-ketoesters 2a-2g using cationic iridium precatalysts results in reductive C-C coupling to afford , beta gamma-unsaturated alpha-hydroxyesters 3a-3f and 4a-4e and 4g, which are formed in excellent yield, with complete control of olefin geometry and, in most cases, with excellent regiocontrol. Similar levels of selectivity are observed across a range of alkynes 1c-1h. Reductive coupling of 3-hexyne 1a and alpha-ketoester 2a under an atmosphere of elemental deuterium provides the monodeuterated product deuterio-3a, consistent with a catalytic mechanism involving alkyne-carbonyl oxidative coupling followed by hydrogenolysis of the resulting oxametallacycle.

  DOI：

  10.1021/ja0670815

文献信息

• Iridium-Catalyzed C−C Bond Forming Hydrogenation:  Direct Regioselective Reductive Coupling of Alkyl-Substituted Alkynes to Activated Ketones
  作者：Ming-Yu Ngai、Andriy Barchuk、Michael J. Krische

  DOI：10.1021/ja0670815

  日期：2007.1.1

  commercially available alkyl-substituted alkynes, 3-hexyne 1a and 1-phenylpropyne 1b, in the presence of alpha-ketoesters 2a-2g using cationic iridium precatalysts results in reductive C-C coupling to afford , beta gamma-unsaturated alpha-hydroxyesters 3a-3f and 4a-4e and 4g, which are formed in excellent yield, with complete control of olefin geometry and, in most cases, with excellent regiocontrol. Similar levels of selectivity are observed across a range of alkynes 1c-1h. Reductive coupling of 3-hexyne 1a and alpha-ketoester 2a under an atmosphere of elemental deuterium provides the monodeuterated product deuterio-3a, consistent with a catalytic mechanism involving alkyne-carbonyl oxidative coupling followed by hydrogenolysis of the resulting oxametallacycle.