(+/-)-10a-methyl-1,9,10,10a-tetrahydro-(2H)-phenanthren-3-one | 63783-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (+/-)-10a-methyl-1,9,10,10a-tetrahydro-(2H)-phenanthren-3-one
• 英文别名: 3-Keto-10a-methyl-1,2,3,9,10,10a-hexahydro-phenanthren；10a-Methyl-1,9,10,10a-tetrahydro-2H-phenanthren-3-on；10a-Methyl-1,9,10,10a-tetrahydro-3(2H)-phenanthrenone；10a-methyl-1,2,9,10-tetrahydrophenanthren-3-one
• CAS: 63783-22-2
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: GONYVNMFEDYGMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (+/-)-10a-methyl-1,9,10,10a-tetrahydro-(2H)-phenanthren-3-one 在 palladium on activated charcoal chromium(VI) oxide 、 硫酸 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 丙酮 、 甲苯 为溶剂， 25.0 ℃ 、2.0 MPa 条件下， 反应 28.0h， 生成 (4aS,10aS)-10a-Methyl-3-phenyl-1,2,4a,9,10,10a-hexahydro-phenanthrene
  参考文献：
  名称：

  Enthalpy and Entropy of Conjugative Interaction in a Nearly Coplanar Styrene and Cinnamyl Radical

  摘要：

  Conjugative interaction in styrenes designed to constrain the dihedral angle between the planes of the phenyl and olefinic groups near to coplanarity (21 degrees by X-ray) is greater by 0.7 kcal mol(-1) than that in a styrene in which the phenyl group is unconstrained (ad libitum) (-35 degrees by MM2 molecular mechanical calculation). Conjugative interaction in a cinnamyl radical similarly constrained to maintain the phenyl and allyl moieties nearly coplanar (15 degrees by MM2) is greater by 1.1 kcal mol(-1) than in a cinnamyl radical in which the phenyl group is ad libitum. Efforts to separate the contribution of pi-electron delocalization from the nonbonded steric factor by employing MM2 calculations proved quantitatively unsatisfactory.

  DOI：

  10.1021/ja983088d
• 作为产物：
  描述：

  4a-methyl-4,4a,9,10-tetrahydro-3H-phenanthren-2-one 在 PPA 作用下， 生成 (+/-)-10a-methyl-1,9,10,10a-tetrahydro-(2H)-phenanthren-3-one
  参考文献：
  名称：

  A Novel Rearrangement of α,β-Unsaturated Ketones

  摘要：

  DOI：

  10.1246/bcsj.37.151

文献信息

• Isoe; nakazaki, Chemistry and industry, 1959, p. 1574
  作者：Isoe、nakazaki

  DOI：——

  日期：——
• Solvolytic rearrangements accompanied by multiple alkyl shifts
  作者：Howard W. Whitlock、Larry E. Overman

  DOI：10.1021/ja00738a026

  日期：1971.5
• A Novel Rearrangement of α,β-Unsaturated Ketones
  作者：Sachihiko Isoe、Masao Nakazaki

  DOI：10.1246/bcsj.37.151

  日期：1964.2
• Enthalpy and Entropy of Conjugative Interaction in a Nearly Coplanar Styrene and Cinnamyl Radical
  作者：W. v. E. Doering、Johannes Benkhoff、Liming Shao

  DOI：10.1021/ja983088d

  日期：1999.2.1

  Conjugative interaction in styrenes designed to constrain the dihedral angle between the planes of the phenyl and olefinic groups near to coplanarity (21 degrees by X-ray) is greater by 0.7 kcal mol(-1) than that in a styrene in which the phenyl group is unconstrained (ad libitum) (-35 degrees by MM2 molecular mechanical calculation). Conjugative interaction in a cinnamyl radical similarly constrained to maintain the phenyl and allyl moieties nearly coplanar (15 degrees by MM2) is greater by 1.1 kcal mol(-1) than in a cinnamyl radical in which the phenyl group is ad libitum. Efforts to separate the contribution of pi-electron delocalization from the nonbonded steric factor by employing MM2 calculations proved quantitatively unsatisfactory.

表征谱图