1-(4-methylnaphthalen-1-yl)ethyl acetate | 147701-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-methylnaphthalen-1-yl)ethyl acetate
• CAS: 147701-92-6
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: FZKVTGUHFCBHBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-methylnaphthalen-1-yl)ethyl acetate 在 氧气 、 tetraphenylporphyrin 作用下， 以 氘代氯仿 为溶剂， 反应 6.0h， 生成 Acetic acid 1-(8-methyl-9,10-dioxa-tricyclo[6.2.2.0^2,7]dodeca-2,4,6,11-tetraen-1-yl)-ethyl ester
  参考文献：
  名称：

  Diastereoselective Photooxygenation of Chiral Naphthyl Alcohols: The Hydroxy Group Directing Effect in Singlet Oxygen [4+2] Cycloaddition to Arenes

  摘要：

  A series of chiral naphthyl alcohol derivatives 1 was prepared and submitted to sensitized photooxygenation. The corresponding endoperoxides 2 were formed in high yields through [4 + 2] cycloaddition of singlet oxygen. The pi-facial selectivity of singlet oxygen attack was determined and the stereochemistry of the product assigned for representative cases (1a,h) by X-ray analysis of the triols 3 derived from the endoperoxides by reduction. In the photooxygenation of the alcohols 1a-g in nonpolar solvents, the (alpha R*,1R*,4S*)-configurated endoperoxides 2a-g were formed preferentially (diastereomeric ratio (dr) greater than or equal to 85:15). Increase in solvent polarity or protection of the hydroxy group as the acetate in 1i or as the silyl ether in 1j led to substantial loss of diastereoselectivity. Placement of a methyl group at C2, as in alcohol 1h, gave high but opposite pi-facile selectivity (dr = 94:6), i.e., (alpha R*,1S*,4R*)-2h was formed as major product. The observed substitution effects on the pi-facial selectivity are rationalized in terms of steric and electronic control. Thus, hydrogen bonding operates between the unprotected hydroxy group and the incoming singlet oxygen dienophile. Peri strain leads to an effective energy discrimination of the respective diastereomeric transition states and, consequently, high pi-facial selectivities. An alkyl substituent at C2, however, induces additional ortho strain of 1,3-allylic origin, which overrides the effect of peri strain to afford highly selectively the opposite stereoisomer.

  DOI：

  10.1021/ja00130a006
• 作为产物：
  描述：

  4-Methyl-1-naphthylmagnesium bromide 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 生成 1-(4-methylnaphthalen-1-yl)ethyl acetate
  参考文献：
  名称：

  手性萘衍生物与单线态氧的非对映选择性[4 + 2]环加成中的取代基作用

  摘要：

  由1-溴-4-甲基萘制备了八种在立体异构中心具有各种官能团的手性衍生物1，其与单线态氧导致立体电子起源的取代基依赖性π-面选择性中的相应的内过氧化物2。

  DOI：

  10.1016/s0040-4039(00)73346-6