3-{[2-(hydroxymethyl)naphthalen-1-yl]methyl}-pentan-3-ol | 1028202-42-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-{[2-(hydroxymethyl)naphthalen-1-yl]methyl}-pentan-3-ol
• CAS: 1028202-42-7
• 化学式: C₁₇H₂₂O₂
• 分子量: 258.36
• InChiKey: JZXHPYSHMISNPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-{[2-(hydroxymethyl)naphthalen-1-yl]methyl}-pentan-3-ol 在 磷酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以86%的产率得到2,2-diethyl-2,4-dihydrobenzo[f]isochroman
  参考文献：
  名称：

  Regioselective reductive opening of substituted phthalans: synthetic applications

  摘要：

  The reductive opening of substituted phthalans 6, 11, 12, 20, 21 and 28 with lithium and a catalytic amount of DTBB leads to the formation of corresponding functionalised organolithium intermediates 8, 15, 16, 23, 25 and 29+30 in a regioselective manner. The further reaction of these dianions with different electrophiles, mainly carbonyl compounds, gives the expected functionalised benzylic alcohols 9, 17, 18, 24, 26 and 31+32. The observed stereochemistry can be easily explained taking into account the values of the electron densities deduced by semiempirical PM3 calculations. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.072
• 作为产物：
  描述：

  1,3-dihydronaphtho[1,2-c]furan 、 3-戊酮 在 4,4'-二叔丁基苯并 lithium 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 3.33h， 以51%的产率得到3-{[2-(hydroxymethyl)naphthalen-1-yl]methyl}-pentan-3-ol
  参考文献：
  名称：

  Regioselective reductive opening of substituted phthalans: synthetic applications

  摘要：

  The reductive opening of substituted phthalans 6, 11, 12, 20, 21 and 28 with lithium and a catalytic amount of DTBB leads to the formation of corresponding functionalised organolithium intermediates 8, 15, 16, 23, 25 and 29+30 in a regioselective manner. The further reaction of these dianions with different electrophiles, mainly carbonyl compounds, gives the expected functionalised benzylic alcohols 9, 17, 18, 24, 26 and 31+32. The observed stereochemistry can be easily explained taking into account the values of the electron densities deduced by semiempirical PM3 calculations. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.072