benzyl 3-(1-methyl-2-oxocyclopentyl)propanoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 3-(1-methyl-2-oxocyclopentyl)propanoate
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: QORRSHMNSNPWKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-甲基环戊酮 、 丙烯酸苄酯 在 苄胺 作用下， 以 甲苯 为溶剂， 反应 28.0h， 以74%的产率得到benzyl 3-(1-methyl-2-oxocyclopentyl)propanoate
  参考文献：
  名称：

  Primary Amine, Thiourea-Based Dual Catalysis Motif for Synthesis of Stereogenic, All-Carbon Quaternary Center-Containing Cycloalkanones

  摘要：

  The enantioselective synthesis of alpha,alpha-disubstituted cycloalkanones has been developed using a primary amine, thiourea-based dual catalysis pathway. A range of electrophiles and ring sizes are tolerated under the reaction conditions. A possible catalytic cycle is presented to explain the reactivity.

  DOI：

  10.1021/ol301272r

文献信息

• Enantioselective Synthesis of Quaternary Carbon Stereogenic Centers through the Primary Amine-Catalyzed Michael Addition Reaction of α-Substituted Cyclic Ketones at High Pressure
  作者：Ryo Horinouchi、Kouhei Kamei、Riki Watanabe、Nobushige Hieda、Naoki Tatsumi、Keiji Nakano、Yoshiyasu Ichikawa、Hiyoshizo Kotsuki

  DOI：10.1002/ejoc.201500411

  日期：2015.7

  The enantioselective Michael addition reaction of α-substituted cyclic ketones with acrylates was efficiently promoted by a primary amine chiral catalyst under high-pressure conditions (1.0 GPa) in tetrahydrofuran. This method was highly successful for the construction of an all-carbon-substituted quaternary-carbon stereogenic center at the α-position of cyclic ketones in high enantiomeric excess,

  在四氢呋喃中，在高压条件 (1.0 GPa) 下，伯胺手性催化剂有效地促进了 α-取代环酮与丙烯酸酯的对映选择性迈克尔加成反应。该方法在高对映体过量的环酮α位构建全碳取代季碳立体中心非常成功，可方便地应用于(+)-aspidospermidine的正式合成。
• Primary Amine, Thiourea-Based Dual Catalysis Motif for Synthesis of Stereogenic, All-Carbon Quaternary Center-Containing Cycloalkanones
  作者：Jun Yong Kang、Rich G. Carter

  DOI：10.1021/ol301272r

  日期：2012.6.15

  The enantioselective synthesis of alpha,alpha-disubstituted cycloalkanones has been developed using a primary amine, thiourea-based dual catalysis pathway. A range of electrophiles and ring sizes are tolerated under the reaction conditions. A possible catalytic cycle is presented to explain the reactivity.