2-(2-methyl-2-oxiranyl)-1-(9-fluorenyl)naphthalene | 193486-71-4

• 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: 2-(2-methyl-2-oxiranyl)-1-(9-fluorenyl)naphthalene
• 英文别名: 1-(9-Fluorenyl)-2-(2-methyl-2-oxiranyl)naphthalene；2-[1-(9H-fluoren-9-yl)naphthalen-2-yl]-2-methyloxirane
• CAS: 193486-71-4
• 化学式: C₂₆H₂₀O
• 分子量: 348.444
• InChiKey: BLLGTMIFPSRLRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-2-oxiranyl)-1-(9-fluorenyl)naphthalene 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 2-[1-(hydroxymethyl)ethenyl]-1-(9-fluorenyl)naphthalene 、 1-(9-fluorenyl)-2-(1-formylethyl)naphthalene 、 3-methyl[3,4-a]naphthalen-3a,8b-(1,3-butadieno)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan
  参考文献：
  名称：

  摘要：

  X-ray crystallography of the ap-form of the 1-(9-fluorenyl)-2-(2-methyl-2-oxiranyl)naphthalene has revealed that the carbon atom of the oxirane which is connected to the naphthyl group in this compound is almost planar. The specific structural features of the epoxy ring in this compound are caused by sterical effects and by the presence of a pi-system in the immediate vicinity of the oxirane ring. Certain differences have been found also in reactivity of rotational isomers of 2-X-substituted l-[l-(9-fluorenyl)-2-naphthyl]ethyl cations (X = O, S, Se). At X = O arose more deprotonation product from the alpha-position of the oxygen than in reactions of sulfur and selenium-containing analogs. Reactions of epoxides with zinc chloride almost exclusively gave the corresponding aldehydes.

  DOI：

  10.1023/a:1026063919203
• 作为产物：
  描述：

  1-(9-fluorenyl)-2-(1-methylethenyl)naphthalene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以89%的产率得到2-(2-methyl-2-oxiranyl)-1-(9-fluorenyl)naphthalene
  参考文献：
  名称：

  摘要：

  X-ray crystallography of the ap-form of the 1-(9-fluorenyl)-2-(2-methyl-2-oxiranyl)naphthalene has revealed that the carbon atom of the oxirane which is connected to the naphthyl group in this compound is almost planar. The specific structural features of the epoxy ring in this compound are caused by sterical effects and by the presence of a pi-system in the immediate vicinity of the oxirane ring. Certain differences have been found also in reactivity of rotational isomers of 2-X-substituted l-[l-(9-fluorenyl)-2-naphthyl]ethyl cations (X = O, S, Se). At X = O arose more deprotonation product from the alpha-position of the oxygen than in reactions of sulfur and selenium-containing analogs. Reactions of epoxides with zinc chloride almost exclusively gave the corresponding aldehydes.

  DOI：

  10.1023/a:1026063919203

文献信息

• Manifestation of a (distorted) trigonal pyramidal structure of a quadrivalent carbon
  作者：Takanori Hirose、Nobuhiro Morita、Shinji Toyota、Michinori Ōki

  DOI：10.1016/s0040-4039(97)00977-5

  日期：1997.6

  Reactions of ap- and sp-rotamers of 1-(9-fluorenyl)-2-(1-methylethenyl)naphthalene with m-chloroperoxybenzoic acid afforded the corresponding epoxides. Of these, the ap-epoxide was found to contain a carbon atom, the structure of which is a distorted trigonal pyramid, the carbon atom being located close to the center of the base triangle. (C) 1997 Elsevier Science Ltd.