2-(hydroxymethyl)-2-methylcyclopent-4-ene-1,3-dione | 1383003-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(hydroxymethyl)-2-methylcyclopent-4-ene-1,3-dione
• 英文别名: 2-(Hydroxymethyl)-2-methylcyclopent-4-ene-1,3-dione
• CAS: 1383003-39-1
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: UFFSXTDYEABTSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-2-methylcyclopent-4-ene-1,3-dione 在 咪唑 、 1-(3,5-Bis-trifluoromethyl-phenyl)-3-[(S)-((1S,2S,4S,5R)-5-ethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl]-urea 、 4-二甲氨基吡啶 、 三氟甲苯 、 sodium carbonate 、 caesium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 124.17h， 生成
  参考文献：
  名称：

  Organocatalytic Enantioselective Formal C(sp²)–H Alkylation

  摘要：

  An organocatalytic enantioselective formal C(sp(2))-H alkylation is reported. This alkylative desymmetrization of prochiral 2,2-disubstituted cyclopentene-1,3-dione is catalyzed by a bifunctional tertiary aminourea derivative, utilizes air-stable and inexpensive nitroalkanes as the alkylating agents, and delivers synthetically versatile five-membered carbocycles containing an all-carbon quaternary stereogenic center remote from the reaction site in excellent enantioselectivity.

  DOI：

  10.1021/ja5117556
• 作为产物：
  描述：

  (1-methyl-2,5-dioxocyclopentyl)methyl acetate 在 copper(ll) bromide 作用下， 以 甲醇 为溶剂， 以33%的产率得到2-(hydroxymethyl)-2-methylcyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Organocatalytic Enantioselective Formal C(sp²)–H Alkylation

  摘要：

  An organocatalytic enantioselective formal C(sp(2))-H alkylation is reported. This alkylative desymmetrization of prochiral 2,2-disubstituted cyclopentene-1,3-dione is catalyzed by a bifunctional tertiary aminourea derivative, utilizes air-stable and inexpensive nitroalkanes as the alkylating agents, and delivers synthetically versatile five-membered carbocycles containing an all-carbon quaternary stereogenic center remote from the reaction site in excellent enantioselectivity.

  DOI：

  10.1021/ja5117556

文献信息

• Copper(I)-Catalyzed Asymmetric Desymmetrization: Synthesis of Five-Membered-Ring Compounds Containing All-Carbon Quaternary Stereocenters
  作者：Kohsuke Aikawa、Tatsuya Okamoto、Koichi Mikami

  DOI：10.1021/ja3032345

  日期：2012.6.27

  A highly stereoselective catalytic alkylation sequence for the synthesis of highly functionalized and versatile five-membered-ring compounds bearing all-carbon quaternary stereocenters was developed. Enantioselective desymmetrization of achiral cyclopentene-1,3-diones was thus executed by chiral Cu-phosphoramidite catalysts. A variety of complicated cyclopentane derivatives can be synthesized with

  开发了一种高度立体选择性催化烷基化序列，用于合成具有全碳四元立体中心的高度功能化和多功能的五元环化合物。因此，手性 Cu-亚磷酰胺催化剂实现了非手性环戊烯-1,3-二酮的对映选择性去对称化。可以在一锅操作中使用低催化剂负载量合成具有优异立体选择性的各种复杂的环戊烷衍生物。
• Organocatalytic Enantioselective Formal C(sp²)–H Alkylation
  作者：Madhu Sudan Manna、Santanu Mukherjee

  DOI：10.1021/ja5117556

  日期：2015.1.14

  An organocatalytic enantioselective formal C(sp(2))-H alkylation is reported. This alkylative desymmetrization of prochiral 2,2-disubstituted cyclopentene-1,3-dione is catalyzed by a bifunctional tertiary aminourea derivative, utilizes air-stable and inexpensive nitroalkanes as the alkylating agents, and delivers synthetically versatile five-membered carbocycles containing an all-carbon quaternary stereogenic center remote from the reaction site in excellent enantioselectivity.