6-t-Butyl-3-hydroxymethyl-2-naphthol | 203187-47-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-t-Butyl-3-hydroxymethyl-2-naphthol
• 英文别名: 6-tert-butyl-3-(hydroxymethyl)naphthalen-2-ol
• CAS: 203187-47-7
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: KELBSKKHUVYSKA-UHFFFAOYSA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  339.2±12.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-t-Butyl-3-hydroxymethyl-2-naphthol 在 四氯化钛 作用下， 以 1,4-二氧六环 为溶剂， 以31%的产率得到7,17,27,37-Tetratert-butylnonacyclo[31.7.1.13,11.113,21.123,31.04,9.014,19.024,29.034,39]tetratetraconta-1(41),3,5,7,9,11(44),13,15,17,19,21(43),23,25,27,29,31(42),33,35,37,39-icosaene-41,42,43,44-tetrol
  参考文献：
  名称：

  Spirodienone and Bis(spirodienone) Derivatives of Calix[4]naphthalenes

  摘要：

  Calix[4]naphthalenes 11 and 12 in which hydroxyl groups are situated intraannularly can be oxidized with PTMATB and base to form the bis(spirodienone) 13, from 11, and bis(spirodienone) 20-21 and spirodienone 22, from 12. The prototype calix[4]naphthalenes 9 and 10 previously reported by us and which contain similar 1,5 dihydroxy functionalities extrannularly failed to afford the analogous spironaphthalenones. Model studies with the bis(1-hydroxy-2-naphthyl)methanes 8-8f provided support for the putative mechanism proposed for the formation of spirodienone calix[4]arenes and spironaphthalenones. The synthesis of the novel tert-butylcalix[4]naphthalenes 12 is described.

  DOI：

  10.1021/jo971541i
• 作为产物：
  描述：

  Methyl 7-tert-butyl-3-hydroxynaphthalene-2-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到6-t-Butyl-3-hydroxymethyl-2-naphthol
  参考文献：
  名称：

  Spirodienone and Bis(spirodienone) Derivatives of Calix[4]naphthalenes

  摘要：

  Calix[4]naphthalenes 11 and 12 in which hydroxyl groups are situated intraannularly can be oxidized with PTMATB and base to form the bis(spirodienone) 13, from 11, and bis(spirodienone) 20-21 and spirodienone 22, from 12. The prototype calix[4]naphthalenes 9 and 10 previously reported by us and which contain similar 1,5 dihydroxy functionalities extrannularly failed to afford the analogous spironaphthalenones. Model studies with the bis(1-hydroxy-2-naphthyl)methanes 8-8f provided support for the putative mechanism proposed for the formation of spirodienone calix[4]arenes and spironaphthalenones. The synthesis of the novel tert-butylcalix[4]naphthalenes 12 is described.

  DOI：

  10.1021/jo971541i

文献信息

• Chemical reactivity of hydroxymethylnaphthols: hetero-Diels–Alder products of o-naphthoquinomethides derived from 2- and 3-hydroxymethylnaphthols
  作者：Muhammad Ashram、David O. Miller、Paris E. Georghiou

  DOI：10.1039/b200893a

  日期：2002.6.7

  In relation to the syntheses of exo- and endo-calixnaphthalenes, the chemical reactions of several 2- and 3-hydroxymethylnaphthols, as well as other substituted naphthols, with formaldehyde under a variety of condensation reaction conditions were evaluated. In several instances, o-naphthoquinomethides were the putative intermediates which were formed and which resulted in hetero-Diels–Alder [4+2]cyclodimerization

  关于外杯和内杯萘的合成，一些2-和3-羟甲基萘以及其他取代的萘的化学反应萘酚， 和 甲醛在各种缩合反应条件下进行了评估。在某些情况下，邻-萘甲喹啉是形成的假定中间体，可导致杂Diels-Alder [4 + 2]环二聚螺旋产物。
• Spirodienone and Bis(spirodienone) Derivatives of Calix[4]naphthalenes
  作者：Paris E. Georghiou、Muhammad Ashram、Howard J. Clase、John N. Bridson

  DOI：10.1021/jo971541i

  日期：1998.3.1

  Calix[4]naphthalenes 11 and 12 in which hydroxyl groups are situated intraannularly can be oxidized with PTMATB and base to form the bis(spirodienone) 13, from 11, and bis(spirodienone) 20-21 and spirodienone 22, from 12. The prototype calix[4]naphthalenes 9 and 10 previously reported by us and which contain similar 1,5 dihydroxy functionalities extrannularly failed to afford the analogous spironaphthalenones. Model studies with the bis(1-hydroxy-2-naphthyl)methanes 8-8f provided support for the putative mechanism proposed for the formation of spirodienone calix[4]arenes and spironaphthalenones. The synthesis of the novel tert-butylcalix[4]naphthalenes 12 is described.