6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one | 883-07-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one
• 英文别名: 6,8-dimethoxy-3,4-dihydronaphthalen-1(2H)-one；6,8-Dimethoxytetralone；6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one；6,8-Dimethoxy-3,4-dihydro-2H-naphthalin-1-on；6,8-dimethoxy-1-tetralone；6,8-Dimethoxy-tetralon-(1)
• CAS: 883-07-8
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: PXVHOBFCMQGIMG-UHFFFAOYSA-N

物化性质

• 熔点：
  62-64 °C
• 沸点：
  366.0±42.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one 在 叔丁基过氧化氢 、 N,N-二甲基丙烯基脲 、 dirhodium tetrakis(caprolactamate) 、 potassium tert-butylate 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 作用下， 以 四氢呋喃 、 癸烷 、 乙腈 、 苯 为溶剂， 反应 46.75h， 生成 6',8'-dimethoxy-3'-methyl-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-4'(3'H)-one
  参考文献：
  名称：

  Synthesis of carbocyclic analogs of dehydroaltenusin: identification of a stable inhibitor of calf DNA polymerase α

  摘要：

  Syntheses of carbocyclic analogs of dehydroaltenusin tautomers are reported. Both target compounds, cDHA (2,8-dihydroxy-6-methoxy-10a-methyl-10,10a-dihydrophenanthrene-3,9-dione) and cDHAs (4',5dihydroxy-6'-methoxy-2-methylspirolcyclohexa[2,5]diene-1,1'-indene]-3',4(2'H)-dione), were prepared from 3,5-dimethoxybenzaldehyde in 11 and 13 steps, respectively. Unlike dehydroaltenusin, both cDHA and cDHAs are stable and their structures were confirmed by X-ray crystallography. Compound cDHA was found to be active against calf DNA polymerase a but not related isozymes, while the spirocyclic analog cDHAs was inactive. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.08.005
• 作为产物：
  描述：

  3,5-二甲氧基苄醇 在 lithium aluminium tetrahydride 、 PPA 、 氢溴酸 、 三溴化磷 作用下， 以 乙醚 、 苯 为溶剂， 生成 6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Huisgen,R. et al., Justus Liebigs Annalen der Chemie, 1964, vol. 677, p. 21 - 33

  摘要：

  DOI：

文献信息

• Design, synthesis, and biological activity of bicyclic radester analogues as Hsp90 inhibitors
  作者：Vinod D. Jadhav、Adam S. Duerfeldt、Brian S.J. Blagg

  DOI：10.1016/j.bmcl.2009.10.091

  日期：2009.12

  Bicyclic radester analogues have been synthesized and evaluated for Hsp90 inhibitory activity. These analogues induce concentration-dependent degradation of Hsp90-dependent client proteins with the six-membered bicyclic analogues manifesting increased activity versus the five-membered counterparts.

  已经合成并评估了双环 radester 类似物的 Hsp90 抑制活性。这些类似物诱导 Hsp90 依赖性客户蛋白的浓度依赖性降解，六元双环类似物与五元对应物相比表现出更高的活性。
• Intramolecular Friedel–Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol
  作者：Hashim F. Motiwala、Rakesh H. Vekariya、Jeffrey Aubé

  DOI：10.1021/acs.orglett.5b02851

  日期：2015.11.6

  Simple dissolution of an arylalkyl acid chloride in 1,1,1,3,3,3-hexafluoro-2-propanol promotes an intramolecular Friedel–Crafts acylation without additional catalysts or reagents. This reaction is operationally trivial in both execution and product isolation (only requiring concentration followed by purification) and accommodates a broad range of substrates. Preliminary studies that bear upon potential

  芳基烷基酰氯在1,1,1,3,3,3-六氟-2-丙醇中的简单溶解可促进分子内Friedel-Crafts酰化反应，而无需其他催化剂或试剂。该反应在操作和产物分离上都操作上很简单（只需要浓缩后再纯化），并适用于各种各样的底物。据报道涉及潜在反应机理的初步研究。
• Urokinase inhibitors
  申请人：Abbott Laboratories

  公开号：US06258822B1

  公开（公告）日：2001-07-10

  Compounds having the formula are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions and a method of inhibiting urokinase in a mammal.

  具有该公式的化合物是尿激酶的抑制剂，对于尿激酶在其中发挥作用的疾病的治疗是有用的。还公开了抑制尿激酶的组合物和在哺乳动物中抑制尿激酶的方法。
• Ukokinase inhibitors
  申请人：Abbott Laboratories

  公开号：US06284796B1

  公开（公告）日：2001-09-04

  Compounds having the formula are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions and a method of inhibiting urokinase in a mammal.

  具有该化学式的化合物是尿激酶的抑制剂，对于尿激酶在某些疾病治疗中起作用是有用的。还公开了抑制尿激酶的组合物和在哺乳动物中抑制尿激酶的方法。
• Synthesis of C4C5 Cycloalkyl-Fused and C6-Modified Chromans via<i>ortho</i>-Quinone Methides
  作者：Kassrin Tangdenpaisal、Kanokpish Chuayboonsong、Patchaya Sukjarean、Varisa Katesampao、Nok Noiphrom、Somsak Ruchirawat、Poonsakdi Ploypradith

  DOI：10.1002/asia.201403356

  日期：2015.4

  from 3,5‐dimethoxybenzaldehyde, some functionalized 2,3,4‐trisubstituted tricyclic 4,5‐cycloalkyl‐fused and 6‐modified chromans could be prepared via ortho‐quinone methides (o‐QMs)/hetero‐Diels–Alder (HDA) reactions of the appropriate precursors. The bromide at C6 served as a handle for introducing other substituents through palladium‐catalyzed cross‐coupling reactions and other functional‐group transformations

  从3,5-二甲氧基苯甲醛开始，可以通过邻醌甲基（o -QMs）/杂Diels-Alder（ HDA）适当前体的反应。C6处的溴化物可作为通过钯催化的交叉偶联反应和其他官能团转化引入其他取代基的方法。在[PtCl 4 ]催化下可获得中等至高产率（高达80％）和非对映选择性（高达> 99：1）。优选内切环加成反应中的过渡态中管理在C2的立体化学结果起到了重要作用 C3 C4。在构型上固定Ë双环的几何ö -QMs影响了环加成反应，以有利于C2  C4顺式关系。