(E)-methyl-6-oxohept-4-enoate | 81768-80-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-methyl-6-oxohept-4-enoate
• 英文别名: Methyl 6-oxo-4(E)-heptenoate；methyl (4E)-6-oxo-4-heptenoate；methyl (E)-6-oxohept-4-enoate
• CAS: 81768-80-1
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: UFVARGSIDAFAPG-HWKANZROSA-N

物化性质

• 沸点：
  208.1±23.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (E)-methyl-6-oxohept-4-enoate 在 sodium tetrahydroborate 、 硫酸 、 三氟化硼乙醚 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 3-{(3aS,4R,6S)-1-[1-Acetoxy-eth-(E)-ylidene]-6-hydroxy-2,3,3a,4,5,6-hexahydro-1H-inden-4-yl}-propionic acid methyl ester
  参考文献：
  名称：

  Efficient de novo construction of the indanepropionic acid precursor of 11-oxo steroids. An improved internal Diels-Alder sequence

  摘要：

  DOI：

  10.1021/ja00377a052
• 作为产物：
  描述：

  1-甲氧基-2-甲基环己-1,4-二烯 在 臭氧 作用下， 生成 (E)-methyl-6-oxohept-4-enoate
  参考文献：
  名称：

  Efficient de novo construction of the indanepropionic acid precursor of 11-oxo steroids. An improved internal Diels-Alder sequence

  摘要：

  DOI：

  10.1021/ja00377a052

文献信息

• Straightforward Access to α-Methylamines through Cross-Metathesis
  作者：Michèle Bertrand、Gérard Gil、Stéphane Gastaldi、Florent Poulhès、Rémy Sylvain、Patricia Perfetti

  DOI：10.1055/s-0029-1218672

  日期：2010.4

  A two-step procedure involving cross-metathesis and reductive amination enables easy access to α-methylamines and α,α′-dimethyldiamines from a wide variety of terminal olefins.

  一种涉及交叉易位和还原胺化的两步过程，使得从多种末端烯烃轻松制备α-甲基胺和α,α′-二甲基二胺成为可能。
• Copper-Catalyzed Tandem Conjugate Addition−Electrophilic Trapping:  Ketones, Esters, and Nitriles as Terminal Electrophiles
  作者：Kyriacos Agapiou、David F. Cauble、Michael J. Krische

  DOI：10.1021/ja030603l

  日期：2004.4.1

  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.
• Stereochemical Dependence of Base-Catalyzed Cleavage of Cyclic Peroxy Ketals
  作者：Barry B. Snider、Zhongping Shi、Steven V. O'Neil、Kevin D. Kreutter、Tracy L. Arakaki

  DOI：10.1021/jo00086a022

  日期：1994.4

  Base-catalyzed decomposition of cyclic peroxy ketals 1c, 2c, 14, and 16 shows a strong stereochemical dependence. Isomers 2c and 16 with a pseudoequatorial hydrogen undergo a fast antiperiplanar E2 elimination to afford ene diones 4 and 17 that react further. Ester 1c, with a pseudoaxial hydrogen and a pseudoequatorial acetate side chain, reacts slowly to form the enolate, which undergoes an S(N)2 reaction to give epoxide 3. Peroxy ketals 14 and 15 are stable in base. Peroxy acetals 19 and 20 undergo a faster E2 elimination with loss of the pseudoequatorial acetal proton to provide alkoxide ester 21 that reacts further.
• Efficient de novo construction of the indanepropionic acid precursor of 11-oxo steroids. An improved internal Diels-Alder sequence
  作者：Gilbert Stork、David Sherman

  DOI：10.1021/ja00377a052

  日期：1982.6