1-(8-甲基萘-1-基)乙烷-1-醇 | 81603-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-(8-甲基萘-1-基)乙烷-1-醇
• 英文名称: 1-(8-Methylnaphthalen-1-yl)ethanol
• CAS: 81603-33-0
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: MKLDRFKUCXGLNE-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C
• 沸点：
  333.4±11.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(8-甲基萘-1-基)乙烷-1-醇 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 2.5h， 生成 8-Ethyl-1-methyl-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Synthesis of peri-substituted naphthalenes and tetralins

  摘要：

  DOI：

  10.1021/jo00134a015
• 作为产物：
  描述：

  3H-2-氧杂-1H-非那烯-1-酮 在 palladium on activated charcoal 盐酸 、 水 、 氢气 、 二异丁基氢化铝 作用下， 以 乙醚 、 溶剂黄146 为溶剂， 290.0 ℃ 、413.69 kPa 条件下， 反应 53.5h， 生成 1-(8-甲基萘-1-基)乙烷-1-醇
  参考文献：
  名称：

  Synthesis of peri-substituted naphthalenes and tetralins

  摘要：

  DOI：

  10.1021/jo00134a015

文献信息

• Diastereoselective Photooxygenation of Chiral Naphthyl Alcohols: The Hydroxy Group Directing Effect in Singlet Oxygen [4+2] Cycloaddition to Arenes
  作者：Waldemar Adam、Eva Maria Peters、Karl Peters、Michael Prein、Hans Georg von Schnering

  DOI：10.1021/ja00130a006

  日期：1995.6

  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.
• POURAHMADY, N.;VICKERY, E. H.;EISENBRAUN, E. J., J. ORG. CHEM., 1982, 47, N 13, 2590-2593
  作者：POURAHMADY, N.、VICKERY, E. H.、EISENBRAUN, E. J.

  DOI：——

  日期：——
• GORE P. H.; MIRI A. Y.; RINAUDO J.; BONNIER J.-M., BULL. SOC. CHIM. FRANCE, 1978, PART. 2, NO 1-2, 104-108
  作者：GORE P. H.、 MIRI A. Y.、 RINAUDO J.、 BONNIER J.-M.

  DOI：——

  日期：——
• Synthesis of peri-substituted naphthalenes and tetralins
  作者：Naser Pourahmady、Euin H. Vickery、Edmund J. Eisenbraun

  DOI：10.1021/jo00134a015

  日期：1982.6