2-methyl-2-(4-oxopent-2-enyl)indan-1,3-dione | 690660-60-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-methyl-2-(4-oxopent-2-enyl)indan-1,3-dione
• 英文别名: 2-methyl-2-[(E)-4-oxopent-2-enyl]indene-1,3-dione
• CAS: 690660-60-7
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: QZOPPXYLIDWOQI-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethylzinc 、 2-methyl-2-(4-oxopent-2-enyl)indan-1,3-dione 在 copper(II) bis(trifluoromethanesulfonate) 、 亚磷酸三乙酯 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (2S,3R,3aR,8aS)-3-Acetyl-2-ethyl-3a-hydroxy-8a-methyl-2,3,3a,8a-tetrahydro-1H-cyclopenta[a]inden-8-one 、 (2S,3R,3aS,8aR)-3-Acetyl-2-ethyl-3a-hydroxy-8a-methyl-2,3,3a,8a-tetrahydro-1H-cyclopenta[a]inden-8-one
  参考文献：
  名称：

  Copper-Catalyzed Tandem Conjugate Addition−Electrophilic Trapping:  Ketones, Esters, and Nitriles as Terminal Electrophiles

  摘要：

  Exposure of enone substrates 1a-18a, which possess appendant ketone, ester, and nitrile moieties, to Et2Zn in the presence of catalytic Cu(OTf)2/P(OEt)3 provides the cyclized products in good to excellent yields and diastereoselectivities. These results represent the first use of ketones, esters, and nitriles as terminal electrophiles in Cu-catalyzed conjugate addition-electrophilic trapping.

  DOI：

  10.1021/ja030603l
• 作为产物：
  描述：

  2-allyl-2-methyl-1,3-indandione 在 臭氧 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 13.0h， 生成 2-methyl-2-(4-oxopent-2-enyl)indan-1,3-dione
  参考文献：
  名称：

  Copper-Catalyzed Tandem Conjugate Addition−Electrophilic Trapping:  Ketones, Esters, and Nitriles as Terminal Electrophiles

  摘要：

  Exposure of enone substrates 1a-18a, which possess appendant ketone, ester, and nitrile moieties, to Et2Zn in the presence of catalytic Cu(OTf)2/P(OEt)3 provides the cyclized products in good to excellent yields and diastereoselectivities. These results represent the first use of ketones, esters, and nitriles as terminal electrophiles in Cu-catalyzed conjugate addition-electrophilic trapping.

  DOI：

  10.1021/ja030603l