ethyl (E)-3-ethyl-2-hydroxy-2-(thiophen-2-yl)hex-3-enoate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-3-ethyl-2-hydroxy-2-(thiophen-2-yl)hex-3-enoate
• 英文别名: ethyl (E)-3-ethyl-2-hydroxy-2-thiophen-2-ylhex-3-enoate
• 化学式: C₁₄H₂₀O₃S
• 分子量: 268.377
• InChiKey: LDNNFWGAAUVHKQ-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-己炔 、 2-噻酚乙酯乙酸乙酯 在 Ir(cod)2BARF 1,1'-双(二苯基膦)二茂铁 、 三苯基乙酸 、 氢气 作用下， 以 甲苯 为溶剂， 60.0 ℃ 、101.32 kPa 条件下， 反应 1.0h， 以85%的产率得到ethyl (E)-3-ethyl-2-hydroxy-2-(thiophen-2-yl)hex-3-enoate
  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.