4-methyl-7-oxo-hept-2-enoic acid ethyl ester | 186535-74-0

• 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: 4-methyl-7-oxo-hept-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-4-methyl-7-oxohept-2-enoate
• CAS: 186535-74-0
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: MLPQJOPLSHLVJH-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  4-methyl-7-oxo-hept-2-enoic acid ethyl ester 在 二苯甲酮 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.42h， 生成
  参考文献：
  名称：

  使用硫缩醛基团进行自由基环化以产生自由基

  摘要：

  研究了几种杂环基的产生和环化。通过二苯甲酮三联体从1,3-二硫杂环戊烷，1,3-二硫杂环戊烷和1,3-氧杂蒽环上夺氢产生了相应的杂环基，这些杂环基通过分子内加成α，β-不饱和酯而得到环化产物。还研究了使用手性缩醛的非对映选择性自由基环化。

  DOI：

  10.1016/0040-4020(96)00511-x
• 作为产物：
  描述：

  6-(tetrahydropyran-2-yloxy)hex-1-ene 在 六甲基磷酰三胺 、 sodium periodate 、 四氧化锇 、 4 A molecular sieve 、 Celite 、 氯化铵 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 pyridinium chlorochromate 、 lithium diisopropyl amide 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 叔丁醇 、 苯 为溶剂， 反应 16.0h， 生成 4-methyl-7-oxo-hept-2-enoic acid ethyl ester
  参考文献：
  名称：

  使用硫缩醛基团进行自由基环化以产生自由基

  摘要：

  研究了几种杂环基的产生和环化。通过二苯甲酮三联体从1,3-二硫杂环戊烷，1,3-二硫杂环戊烷和1,3-氧杂蒽环上夺氢产生了相应的杂环基，这些杂环基通过分子内加成α，β-不饱和酯而得到环化产物。还研究了使用手性缩醛的非对映选择性自由基环化。

  DOI：

  10.1016/0040-4020(96)00511-x

文献信息

• Diastereoselective Synthesis of Cycloalkylamines by Samarium Diiodide-Promoted Cyclizations of α-Amino Radicals Derived from α-Benzotriazolylalkenylamines
  作者：José M. Aurrecoechea、Beatriz López、Alvaro Fernández、Ana Arrieta、Fernando P. Cossío

  DOI：10.1021/jo960957d

  日期：1997.2.1

  The condensation of omega-unsaturated aldehydes with benzotriazole and secondary amines affords alpha-benzotriazolylalkenylamines that exist in solution as mixtures of the corresponding benzotriazol-1-yl and benzotriazol-2-yl isomers resulting from their rapid dissociation into iminium cations and the benzotriazolyl anion. The reduction of these adducts with samarium diiodide (SmI2) takes place with formation of the benzotriazolyl anion and alpha-amino alkenyl radicals that undergo 5- or 6-exo-trig cyclizations leading to substituted cycloalkyl- or cycloheteroalkylamines. The presence of an electron-withdrawing substituent in the alkene subunit is required for efficient cyclizations. The formation of cyclopentylamines takes place with unusually high 1,5-cis selectivity (hex-5-enyl radical numbering), and the presence of a 2- or 4-Me substituent also imparts high 1,2- or 1,4-trans stereoinduction, respectively. The corresponding six-membered rings, however, are formed with low diastereoselectivity. Semiempirical calculations performed on model systems suggest that a stabilizing secondary orbital interaction between the amino group and the electron-deficient alkene might in part account for the enhanced cis-selectivity encountered.
• The effect of pre-existing stereocenters in the intramolecular asymmetric Stetter reaction
  作者：Nathan T. Reynolds、Tomislav Rovis

  DOI：10.1016/j.tet.2005.03.121

  日期：2005.6

  A series of disubstituted cyclopentanones have been synthesized by the intramolecular Stetter reaction. Racemic substrates containing one chiral center were used, allowing us the opportunity to observe a parallel kinetic resolution in the synthesis of 2,3- and 2,4disubstituted cyclopentanones. The Stetter reaction of 2,5-disubstituted cyclopentanones proved to be substrate controlled, resulting in the selective formation of the cis-diasteroiners with low ee. (c) 2005 Elsevier Ltd. All rights reserved.
• Radical cyclization using a thioacetal group for radical generation
  作者：Atsushi Nishida、Norio Kawahara、Mayumi Nishida、Osamu Yonemitsu

  DOI：10.1016/0040-4020(96)00511-x

  日期：1996.7

  The generation and cyclization of several heterocyclic radicals were investigated. The hydrogen abstraction from 1,3-dithiane, 1,3-dithiolane, and 1,3-oxathiane rings by a benzophenone triplet generated the corresponding heterocyclic radicals, which gave the cyclized products by intramolecular addition to α,β-unsaturated esters. Diastereoselective radical cyclization using chiral acetals was also investigated

  研究了几种杂环基的产生和环化。通过二苯甲酮三联体从1,3-二硫杂环戊烷，1,3-二硫杂环戊烷和1,3-氧杂蒽环上夺氢产生了相应的杂环基，这些杂环基通过分子内加成α，β-不饱和酯而得到环化产物。还研究了使用手性缩醛的非对映选择性自由基环化。