2,5-dimethylcyclohept-4-en-1-one | 72272-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dimethylcyclohept-4-en-1-one
• 英文别名: 2,5-Dimethyl-cyclohept-4-en-1-on；2.5-Dimethylcyclohept-4-en-1-on；4-Cyclohepten-1-one, 2,5-dimethyl-
• CAS: 72272-31-2
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: JXCRGNLCWCFASJ-UHFFFAOYSA-N

物化性质

• 沸点：
  207.1±9.0 °C(Predicted)
• 密度：
  0.909±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,5-dimethylcyclohept-4-en-1-one 在 吡啶 、 lithium aluminium tetrahydride 、 (S)-(-)- α-甲基苄胺 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 121.0h， 生成 3-[(1S)-1,4-dimethyl-7-triethylsilyloxycyclohept-3-en-1-yl]propyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Liverwort Diterpenes, (−)-13(15)E,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene and (−)-13(15)Z,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene, by Use of the Ring Closing Metathesis Reaction Applied to Seven-Membered Carbocycles with a Trisubstituted Double Bond

  摘要：

  Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3P,4P-epoxy18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration.

  DOI：

  10.1021/jo020287d
• 作为产物：
  描述：

  ethyl 2-allyl-6-methyl-3-oxo-6-heptenoate 在 Grubbs catalyst first generation 、 水 、 sodium hydride 、 lithium chloride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 苯 为溶剂， 反应 51.0h， 生成 2,5-dimethylcyclohept-4-en-1-one
  参考文献：
  名称：

  Total Synthesis and Absolute Configuration of Liverwort Diterpenes, (−)-13(15)E,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene and (−)-13(15)Z,16E-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene, by Use of the Ring Closing Metathesis Reaction Applied to Seven-Membered Carbocycles with a Trisubstituted Double Bond

  摘要：

  Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3P,4P-epoxy18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration.

  DOI：

  10.1021/jo020287d

文献信息

• Asymmetric synthesis of a highly functionalized bicyclo[3.2.2]nonene derivative
  作者：Toshiki Tabuchi、Daisuke Urabe、Masayuki Inoue

  DOI：10.3762/bjoc.9.74

  日期：——

  The stereoselective Diels-Alder reaction between an optically active 1,4-dimethylcycloheptadiene and acrolein was effectively promoted by TBSOTf to produce a bicyclo[3.2.2]nonene derivative bearing two quaternary carbons. Seven additional transformations from the obtained bicycle delivered the C 2-symmetric bicyclo[3.3.2]decene derivative, a key intermediate in our synthetic study of ryanodine.

  TBSOTf 有效地促进了光学活性 1,4-二甲基环庚二烯和丙烯醛之间的立体选择性 Diels-Alder 反应，以产生带有两个季碳的双环 [3.2.2] 壬烯衍生物。来自获得的自行车的另外七次转化产生了 C 2 对称双环 [3.3.2] 癸烯衍生物，这是我们合成蓝尼定的关键中间体。
• Total Synthesis and Absolute Configuration of Liverwort Diterpenes, (−)-13(15)<i>E</i>,16<i>E</i>-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene and (−)-13(15)<i>Z</i>,16<i>E</i>-3β,4β-Epoxy-18-hydroxysphenoloba-13(15),16-diene, by Use of the Ring Closing Metathesis Reaction Applied to Seven-Membered Carbocycles with a Trisubstituted Double Bond
  作者：Katsuyuki Nakashima、Kosuke Inoue、Masakazu Sono、Motoo Tori

  DOI：10.1021/jo020287d

  日期：2002.8.1

  Seven-membered cyclic compounds possessing trisubstituted double bonds have been effectively constructed employing the Grubbs catalyst to effect olefin metathesis. The keto ester does not undergo cyclization; however, alcohols protected by the silyl groups smoothly cyclized into seven-membered compounds. The product was successfully converted to (-)-13(15)E,16E-3P,4P-epoxy18-hydroxysphenoloba-13(15),16-diene and (-)-13(15)Z,16E-3beta,4beta-epoxy-18-hydroxysphenoloba-13(15),16-diene, liverwort diterpenes isolated from Anastrophyllum auritum to establish the absolute configuration.