methyl 3-methyl-5-oxo-1-phenylcyclohex-3-enecarboxylate | 910311-20-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-methyl-5-oxo-1-phenylcyclohex-3-enecarboxylate
• 英文别名: methyl 3-methyl-5-oxo-1-phenylcyclohex-3-ene-1-carboxylate；Methyl 3-methyl-5-oxo-1-phenylcyclohex-3-ene-1-carboxylate
• CAS: 910311-20-5
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: YIUIRQYAWMZHRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-methyl-5-oxo-1-phenylcyclohex-3-enecarboxylate 、 苯甲醛 在 bismuth(III) chloride 作用下， 以66%的产率得到(E)-methyl 5-oxo-1-phenyl-3-styrylcyclohex-3-enecarboxylate
  参考文献：
  名称：

  Synthesis of 3-methyl-2-cyclohexenones catalyzed by mercury(II) salts and their microwave assisted BiCl3 catalyzed aldol condensations

  摘要：

  HgSO4 catalyzed hydrative cyclization of 1,6-heptadiynes is present. This reaction proceeded smoothly under the mild condition for differently 4-sustituted 1,6-diynic substrates giving corresponding 3-methyl-2-cyclohexenones with high to excellent yield. The microwave assisted aldol condensation of cyclohexenones under the catalysis of BiCl3 afforded 3-styryl-cyclohexenones with high regio- and stereo-selectivity. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.08.037
• 作为产物：
  描述：

  methyl 2-phenyl-2-(prop-2-yn-1-yl)pent-4-ynoate 在 methyl(triphenylphosphine)gold(I) 甲烷磺酸 、 水 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以69%的产率得到methyl 3-methyl-5-oxo-1-phenylcyclohex-3-enecarboxylate
  参考文献：
  名称：

  通过金（I）催化的1，6-二炔的水合环化反应合成2-环己烯酮衍生物。

  摘要：

  发现金（I）配合物（MeAuPPh 3）是用于1，6-二炔的水合环化以形成具有良好至优异收率的相应的3-甲基己-2-烯酮衍生物的高效催化剂。描述了所提出的机制。

  DOI：

  10.1021/jo800974x

文献信息

• Synthesis of 2-Cyclohexenone Derivatives via Gold(I)-Catalyzed Hydrative Cyclization of 1,6-Diynes
  作者：Chen Zhang、Dong-Mei Cui、Li-Ying Yao、Bi-Song Wang、Yong-Zhou Hu、Teruyuki Hayashi

  DOI：10.1021/jo800974x

  日期：2008.10.3

  The gold(I) complex (MeAuPPh3) was found to be a highly effective catalyst for the hydrative cyclization of 1,6-diynes to form the corresponding 3-methyl hex-2-enone derivatives with good to excellent yield. The proposed mechanism is described.

  发现金（I）配合物（MeAuPPh 3）是用于1，6-二炔的水合环化以形成具有良好至优异收率的相应的3-甲基己-2-烯酮衍生物的高效催化剂。描述了所提出的机制。
• Platinum-Catalyzed Hydrative Cyclization of 1,6-Diynes for the Synthesis of 3,5-Substituted Conjugated Cyclohexenones
  作者：Chen Zhang、Jian-Feng Qi、Dong-Mei Cui、Qian Wang、Xiu-Li Wang

  DOI：10.3390/molecules15075045

  日期：——

  We have developed a Pt(COD)Cl2-catalyzed hydrative cyclization of 1,6-diynes leading to the formation of functionalized cyclohexenones in good yields.

  我们开发了 Pt(COD)Cl2 催化的 1,6-二炔水合环化反应，以良好的收率形成官能化环己烯酮。
• Synthesis of 3-methyl-2-cyclohexenones catalyzed by mercury(II) salts and their microwave assisted BiCl3 catalyzed aldol condensations
  作者：Chen Zhang、Bi-Song Wang、Shi-Feng Chen、Shao-Qiao Zhang、Dong-Mei Cui

  DOI：10.1016/j.jorganchem.2010.08.037

  日期：2011.1

  HgSO4 catalyzed hydrative cyclization of 1,6-heptadiynes is present. This reaction proceeded smoothly under the mild condition for differently 4-sustituted 1,6-diynic substrates giving corresponding 3-methyl-2-cyclohexenones with high to excellent yield. The microwave assisted aldol condensation of cyclohexenones under the catalysis of BiCl3 afforded 3-styryl-cyclohexenones with high regio- and stereo-selectivity. (C) 2010 Elsevier B.V. All rights reserved.