1,4,5-trimethoxynaphthalene-2-acetaldehyde | 68280-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4,5-trimethoxynaphthalene-2-acetaldehyde
• 英文别名: 1,4,5-trimethoxynaphth-2-ylacetaldehyde；2-(1,4,5-trimethoxynaphthalen-2-yl)acetaldehyde
• CAS: 68280-99-9
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: YHGYYPSVAYBWTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4,5-trimethoxynaphthalene-2-acetaldehyde 在 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 碳酸氢钠 、 potassium carbonate 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 50.0h， 生成 (4S,5S)-4-hydroxy-5-(1',4',5'-trimethoxynaphth-2'-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  A Dötz benzannulation route to the enantioselective synthesis of (−)- and (+)-juglomycin A

  摘要：

  Two synthetic routes based on a Dotz benzannulation toward the enantioselective synthesis of naphthoquinone antibiotics (-)- and (+)-juglomycin A are described. The stereoinducing step is based on asymmetric dihydroxylation. The syntheses are completed in seven to eight steps from Fischer carbene 12. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.018
• 作为产物：
  描述：

  2-[2-(tert-butyldimethylsilyloxy)ethyl]-4,5-dimethoxynaphthalen-1-ol 在 草酰氯 、 四丁基氟化铵 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.17h， 生成 1,4,5-trimethoxynaphthalene-2-acetaldehyde
  参考文献：
  名称：

  A Dötz benzannulation route to the enantioselective synthesis of (−)- and (+)-juglomycin A

  摘要：

  Two synthetic routes based on a Dotz benzannulation toward the enantioselective synthesis of naphthoquinone antibiotics (-)- and (+)-juglomycin A are described. The stereoinducing step is based on asymmetric dihydroxylation. The syntheses are completed in seven to eight steps from Fischer carbene 12. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.07.018

文献信息

• A general regiospecific synthesis of () 11-deoxyanthracyclinones
  作者：A.V.Rama Ray、V.H. Deshpande、N.Laxma Reddy

  DOI：10.1016/s0040-4039(00)86946-4

  日期：1982.1

  An elegant regiospecific approach for the synthesis of 11-deoxyanthracyclinones is described, involving the Diels-Alder reaction of an appropriate diene with a suitably substituted naphthalene C-D ring synthon.

  描述了一种用于合成11-脱氧蒽环肌酮的优良的区域特异性方法，该方法包括合适的二烯与合适取代的萘CD环合成子的Diels-Alder反应。
• A highly enantioselective synthesis of (−)- and (+)-juglomycin A through Dötz annulation and asymmetric dihydroxylation
  作者：Rodney A. Fernandes、Vijay P. Chavan

  DOI：10.1016/j.tetlet.2008.04.059

  日期：2008.6

  A highly enantioselective synthesis of (−)- and (+)-juglomycin A, a quinone antibiotic is described. The synthesis is completed in eight steps, and 19% overall yield and in a high enantioselectivity of 99.5% [for (−)-juglomycin A] and 98.5% [for (+)-juglomycin A]. The synthetic strategy features an efficient combination of the Dötz annulation reaction and asymmetric dihydroxylation as the keys steps

  描述了对-抗生素-（-）-和（+）-珠霉素A的高度对映选择性合成。合成完成了八个步骤，总产率为19％，对映体选择性高（对（-）-珠红霉素A为99.5％[对（+）-珠红霉素A]为98.5％）。合成策略的关键步骤是有效结合Dötz环化反应和不对称二羟基化反应。
• Stereoselective total synthesis of racemic kalafungin and nanaomycin A
  作者：Tsung-Tee Li、Robert H. Ellison

  DOI：10.1021/ja00487a067

  日期：1978.9
• Efficient, regiospecific synthesis of anthracycline intermediates: total synthesis of daunomycin
  作者：Kathlyn A. Parker、James Kallmerten

  DOI：10.1021/ja00538a029

  日期：1980.8
• A Dötz benzannulation route to the enantioselective synthesis of (−)- and (+)-juglomycin A
  作者：Rodney A. Fernandes、Vijay P. Chavan

  DOI：10.1016/j.tetasy.2011.07.018

  日期：2011.6

  Two synthetic routes based on a Dotz benzannulation toward the enantioselective synthesis of naphthoquinone antibiotics (-)- and (+)-juglomycin A are described. The stereoinducing step is based on asymmetric dihydroxylation. The syntheses are completed in seven to eight steps from Fischer carbene 12. (C) 2011 Elsevier Ltd. All rights reserved.