methyl 2,2-dimethyl-3,5-diphenyl-5-oxopentanoate | 58649-05-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl 2,2-dimethyl-3,5-diphenyl-5-oxopentanoate
• 英文别名: methyl 2,2-dimethyl-5-oxo-3,5-diphenylpentanoate；2,2-dimethyl-5-oxo-3,5-diphenyl-valeric acid methyl ester；2,2-Dimethyl-5-oxo-3,5-diphenyl-valeriansaeure-methylester
• CAS: 58649-05-1
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: ZIVUBIOBIXCDCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  氯仿 、 methyl 2,2-dimethyl-3,5-diphenyl-5-oxopentanoate 、 溴 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Kohler, Heritage, Macleod, American Chemical Journal, 1911, vol. 46, p. 233

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-2,2-Dimethyl-3,5-diphenyl-5-trimethylsilanyloxy-pent-4-enoic acid methyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 2,2-dimethyl-3,5-diphenyl-5-oxopentanoate
  参考文献：
  名称：

  DMSO中简单的环氧三甲基硅烷的自发羟醛和迈克尔加成

  摘要：

  已证明偶极非质子传递溶剂可活化简单的三甲基甲硅烷基乙烯酮缩醛，可在极其简单，温和且无金属的条件下有效地添加助溶剂的羟醛和迈克尔。

  DOI：

  10.1016/s0040-4039(00)00725-5

文献信息

• Pentafluorophenylammonium Trifluoromethanesulfonimide: Mild, Powerful, and Robust Catalyst for Mukaiyama Aldol and Mannich Reactions between Ketene Silyl Acetals and Ketones or Oxime Ethers
  作者：Ryohei Nagase、Jun Osada、Hiroaki Tamagaki、Yoo Tanabe

  DOI：10.1002/adsc.200900869

  日期：——

  (C6F5N+H3⋅NTf2−) promotes Mukaiyama aldol and Mannich reactions using ketene silyl acetals with ketones and oxime ethers, respectively. The present robust method is mild, but powerful enough to utilize less accessible electrophiles such as enolizable ketones and oxime ethers to produce a variety of β‐hydroxy esters and β‐alkoxyamino esters, respectively. Mechanistic investigation revealed in situ generation

  Pentafluorophenylammonium三氟甲磺酰亚胺（C 6 ˚F 5 Ñ + ħ 3 ⋅NTf 2 - ）促进向山羟醛和使用甲硅烷基烯酮缩醛与酮和肟醚，分别曼尼希反应。目前的稳健方法虽然温和，但功能强大，足以利用较难接近的亲电子试剂（例如可烯化的酮和肟醚）分别生产各种β-羟基酯和β-烷氧基氨基酯。机理研究表明，真正的活性催化剂原位生成了三甲基甲硅烷基双硫酰亚胺[Tf 2 N（TMS）]，并通过合理的1 H NMR测量得到了证实。
• Lewis Base-Catalyzed Michael Reactions between Trimethylsilyl Enolate and α,β-Unsaturated Carbonyl Compounds
  作者：Takashi Nakagawa、Hidehiko Fujisawa、Yuzo Nagata、Teruaki Mukaiyama

  DOI：10.1246/bcsj.78.236

  日期：2005.2

  Michael reactions between trimethylsilyl enolates and α,β-unsaturated carbonyl compounds by using a Lewis base catalyst such as lithium benzamide 4 or lithium succinimide 5 in DMF proceeded smoothl...

  苯甲酰胺锂4或琥珀酰亚胺锂5等路易斯碱催化剂在DMF中三甲基甲硅烷基烯醇化物与α,β-不饱和羰基化合物之间的迈克尔反应顺利进行...
• Lewis Base Catalyzed Michael Reaction between Ketene Silyl Acetals and α,β-Unsaturated Carbonyl Compounds
  作者：Teruaki Mukaiyama、Takashi Nakagawa、Hidehiko Fujisawa

  DOI：10.1246/cl.2003.56

  日期：2003.1

  Catalytic Michael reaction between trimethylsilyl enolates and α,β-unsaturated carbonyl compounds by using a Lewis base such as lithium benzamide or lithium succimide in a DMF solvent proceeded smoothly to afford the corresponding Michael adducts.

  三甲基甲硅烷基烯醇化物与α,β-不饱和羰基化合物在DMF溶剂中使用路易斯碱如苯甲酰胺锂或琥珀酰亚胺锂的催化迈克尔反应顺利进行，得到相应的迈克尔加合物。
• Lithium Acetate-catalyzed Michael Reaction between Trimethylsilyl Enolate and α,β-Unsaturated Carbonyl Compound
  作者：Takashi Nakagawa、Hidehiko Fujisawa、Yuzo Nagata、Teruaki Mukaiyama

  DOI：10.1246/cl.2004.1016

  日期：2004.8

  Lithium acetate-catalyzed Michael reaction between trimethylsilyl enolates and α,β-unsaturated carbonyl compounds in DMF proceeded smoothly to afford the corresponding Michael-adducts in good to hi...

  乙酸锂催化三甲基甲硅烷基烯醇化物与DMF中的α,β-不饱和羰基化合物之间的迈克尔反应顺利进行，得到相应的迈克尔加合物。
• THE MICHAEL TYPE REACTION OF O-SILYLATED KETENE ACETALS WITH α,β-UNSATURATED CARBONYL COMPOUNDS PROMOTED BY TITANIUM TETRACHLORIDE
  作者：Kazuhiko Saigo、Masaaki Osaki、Teruaki Mukaiyama

  DOI：10.1246/cl.1976.163

  日期：1976.2.5

  O-Silylated ketene acetals reacted with α,β-unsaturated carbonyl compounds at −78°C in the presence of TiCl4 or in the coexistence of TiCl4 and Ti(OPr-i)4 to afford the corresponding δ-ketoesters in good yields.

  O-甲硅烷基化乙烯酮缩醛与α,β-不饱和羰基化合物在-78°C下在TiCl4存在或TiCl4和Ti(OPr-i)4共存下反应，以良好的产率得到相应的δ-酮酯。