3-hydroxymethyl-6,8-dimethoxynaphthalen-1-ol | 155816-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-hydroxymethyl-6,8-dimethoxynaphthalen-1-ol
• 英文别名: 2-hydroxymethyl-5,7-dimethoxy-4-naphthol；3-(Hydroxymethyl)-6,8-dimethoxynaphthalen-1-ol
• CAS: 155816-93-6
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: WJDXEPKAYDWDNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxymethyl-6,8-dimethoxynaphthalen-1-ol 在 4-二甲氨基吡啶 N-甲基吗啉 、 吡啶 、 chromium dichloride 、 potassium fluoride 、 lithium aluminium tetrahydride 、 18-冠醚-6 、 三氧化硫 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 生成 3-(2-Hydroxypropyl)-6,8-dimethoxynaphthalen-1-ol
  参考文献：
  名称：

  Optically Active Total Synthesis of Calphostin D

  摘要：

  An optically active total synthesis of calphostin D (1a):through dimerization of the chiral o-naphthoquinone 6 has been accomplished. The mechanism of the dimerization has been shown to be an acid-catalyzed process;

  DOI：

  10.1021/jo00087a006
• 作为产物：
  描述：

  4-(乙酰基氧基)-5,7-二甲氧基-2-萘羧酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以91%的产率得到3-hydroxymethyl-6,8-dimethoxynaphthalen-1-ol
  参考文献：
  名称：

  Giles, Robin G. F.; Green, Ivan R.; Knight, Lorraine S., Journal of the Chemical Society. Perkin transactions I, 1994, # 7, p. 853 - 858

  摘要：

  DOI：

文献信息

• Total Synthesis of Amino-Functionalized Calphostin Analogs as Potent and Selective Inhibitors of Protein Kinase C (PKC)
  作者：Hyoyeon Kim、Choon-Ho Song、Dae-Hyuk Kim、Nam-Gin Jung、Seung-Jae Lee、Beom-Tae Kim

  DOI：10.1002/bkcs.10908

  日期：2016.10

  As potential protein kinase C (PKC) inhibitors and photodynamic agents, the novel amino‐functionalized calphostin analog 1,12‐bis((benzoyl‐amino)methyl)‐3,10‐perylenequinone was successfully prepared by dimerization of the key intermediate 3‐(benzoylamino)methyl‐1,2‐naphthoquinone (9), which was synthesized by an efficient and relatively short synthetic sequence (eight steps) with satisfactory overall

  作为潜在的蛋白激酶C（PKC）抑制剂和光动力剂，新型氨基官能化钙磷蛋白类似物1,12-双（（苯甲酰基-氨基）甲基）-3,10-per醌通过关键中间体3- （苯甲酰氨基）甲基1,2-萘醌（9），通过高效且较短的合成步骤（八步）合成，总收率令人满意。通过连续的甲基化和脱甲基反应制备天然形式的per醌12。在我们的合成策略中，1,2-萘醌9的氨基官能度是有益的 可以在合成初期很容易地引入，然后二聚以制备各种可能具有生物活性的per醌。
• Total Synthesis and Structural Confirmation of the Antimalarial Naphthopyrone Lasionectrin
  作者：Vincent L. Poral、Daniel P. Furkert、Margaret A. Brimble

  DOI：10.1021/acs.orglett.5b03202

  日期：2015.12.18

  The total synthesis of lasionectrin, a naphthopyrone metabolite of an Acremonium-like fungus collected in Equatorial Guinea, is reported. Divergent access to four stereoisomers confirmed the natural product to be the enantiomer of the originally proposed structure. Highlights of the synthesis include ring opening of a chiral oxetane using a thiol, a highly E-selective Julia-Kocienski olefination, and a modified Sharpless/Upjohn dihydroxylation. Palladium-catalyzed carbonylative lactonization was used to assemble the fused naphthopyrone ring system.
• Bromination Products of 2‐Substituted 5,7‐Dimethoxy‐4‐Naphthols
  作者：Ivan R. Green、Victor I. Hugo、Mawonga N. Mei

  DOI：10.1080/00397910500377370

  日期：2006.1

  Bromination in acetic acid is favored at C-8 in 5,7-dimethoxy-4-naphthol when the C-2 substituent is methyl carboxylate, whereas C-1 is favored when the C-2 substituent is either acetoxymethylene or methyl.
• Giles Robin G. F., Green Ivan R., Knight Lorraine S., Son Vanessa R. Lee,+, J. Chem. Soc. Perkin Trans. 1, (1994) N 7, S 853-857
  作者：Giles Robin G. F., Green Ivan R., Knight Lorraine S., Son Vanessa R. Lee,+

  DOI：——

  日期：——
• Optically Active Total Synthesis of Calphostin D
  作者：Frank M. Hauser、Dipanjan Sengupta、Stephen A. Corlett

  DOI：10.1021/jo00087a006

  日期：1994.4

  An optically active total synthesis of calphostin D (1a):through dimerization of the chiral o-naphthoquinone 6 has been accomplished. The mechanism of the dimerization has been shown to be an acid-catalyzed process;