1-phenyl-6(Z)-nonen-1-one | 128952-08-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenyl-6(Z)-nonen-1-one
• 英文别名: (Z)-1-phenylnon-6-en-1-one
• CAS: 128952-08-9
• 化学式: C₁₅H₂₀O
• 分子量: 216.323
• InChiKey: QDAGGPOHZADXLM-ARJAWSKDSA-N

物化性质

• 沸点：
  331.6±21.0 °C(Predicted)
• 密度：
  0.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-6(Z)-nonen-1-one 生成 硅烷,(1,1-二甲基乙基)二甲基[(1-苯基-1,6-壬二烯基)氧代]-,(Z,Z)-
  参考文献：
  名称：

  Oxidative cyclization of .delta.,.epsilon.- and .epsilon.,.zeta.-unsaturated enol silyl ethers

  摘要：

  DOI：

  10.1021/jo00303a005
• 作为产物：
  描述：

  (Z)-1-phenylnon-6-en-1-ol 生成 1-phenyl-6(Z)-nonen-1-one
  参考文献：
  名称：

  Oxidative cyclization of .delta.,.epsilon.- and .epsilon.,.zeta.-unsaturated enol silyl ethers

  摘要：

  DOI：

  10.1021/jo00303a005

文献信息

• Mn(III)-Based Oxidative Free-Radical Cyclizations of Unsaturated Ketones
  作者：Bridget McCarthy Cole、Luning Han、Barry B. Snider

  DOI：10.1021/jo961199u

  日期：1996.1.1

  free-radical cyclization of unsaturated ketones is a versatile synthetic procedure with broad applicability. For example, oxidation of cyclopentanone 1a with 2 equiv of Mn(OAc)(3).2H(2)O and 1 equiv of Cu(OAc)(2).H(2)O in AcOH at 80 degrees C for 1.5 h affords 75% of bicyclo[3.2.1]oct-3-en-8-one 8a and 15% of bicyclo[3.2.1]oct-2-en-8-one 9a. Bridged bicyclic ketones that cannot enolize further are isolated

  Mn（III）基的不饱和酮的氧化自由基环化是一种通用的合成方法，具有广泛的适用性。例如，在80摄氏度的条件下，在AcOH中用2当量的Mn（OAc）（3）.2H（2）O和1当量的Cu（OAc）（2）.H（2）O氧化环戊酮1a 1.5小时得到75％的双环[3.2.1] oct-3-en-8-one 8a和15％的双环[3.2.1] oct-2-en-8-one 9a。分离出不能进一步烯醇化的桥联双环酮，收率很高。可以烯化的单环β，γ-不饱和酮被进一步氧化，得到γ-乙酰氧基烯酮。从2-烯丙基环己酮（56a）以52％的收率形成双环[3.3.1] non-2-en-9-one（57a）表明，动力学控制的烯醇化是α-酮自由基形成过程中的决定速率的步骤。各种各样的示例描述了范围，限制，
• Oxidative cyclization of .delta.,.epsilon.- and .epsilon.,.zeta.-unsaturated enol silyl ethers and unsaturated siloxycyclopropanes
  作者：Barry B. Snider、Taesoo Kwon

  DOI：10.1021/jo00034a038

  日期：1992.4

  Oxidative cyclization of delta,epsilon- and epsilon,zeta-unsaturated enol silyl ethers 4a and 4b with cupric triflate and cuprous oxide or ceric ammonium nitrate and sodium bicarbonate in acetonitrile provides the tricyclic ketones 5a and 5b stereoselectively. These cyclizations proceed by oxidation of 4 to the cation radical 24 followed by cyclization of 24 to cation radical 27. This cation radical undergoes a second cyclization to give cation radical 30, which loses the silyl group, undergoes a second oxidation, and loses a proton to give 5. The stereochemistry of the cycloadduct is controlled by the stereochemistry of the enol ether. The Z-enol methyl ether (Z)-65 leads mainly to 5a while the E-enol methyl ether (E)-65 leads mainly to 6a. The oxidative cyclizations of 7, 13, 21, and 43 are also described. Oxidation of alpha-allyl silyl enol ethers 34a and 34b leads mainly to oxidation without cyclization to give the alpha,beta-unsaturated ketones 36a and 36b. Oxidative cyclizations of alkynyl silyl enol ethers 56 and 60 lead to 15 and 64, respectively. Oxidation of siloxycyclopropane 74 with Cu(BF4)2 generates cation radical 75, which cyclizes to 76, which is oxidized to give 21% of cyclopentane 77. This suggests that cation radicals are intermediates in the oxidative dimerization of siloxycyclopropanes.