1,4,5,8-tetramethoxy-naphthalene-2-carbonitrile | 97476-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4,5,8-tetramethoxy-naphthalene-2-carbonitrile
• 英文别名: 1,4,5,8-Tetramethoxynaphthalene-2-carbonitrile
• CAS: 97476-17-0
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: FMZULGXPXQUUOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,4,5,8-tetramethoxy-naphthalene-2-carbonitrile 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 48.0h， 以92%的产率得到1,4,5,8-tetramethoxy-2-naphthoic acid
  参考文献：
  名称：

  Synthesis and Absolute Configuration of Axially Chiral Binaphthoquinones

  摘要：

  合成 (+)-(S)-1′,4-二羟基-2,3′-二甲基-1,2′-萘-5,5′,8,8′-四酮(62)的合成 (62)和 (+)-(S)-4,5′,8′-三羟基-2,3′-二甲基-1,2′-萘-1′,4′,5,8-四酮(55)。 (55），这些化合物与天然存在的 (-)-isodiospyrin 和 (-)-8′-hydroxyisodiospyrin 的异构体。这些 中的二萘基连接是通过噁唑啉化学方法立体选择性地构建的。 使用噁唑啉化学方法立体选择性地构建了这些化合物中的二萘基连接。立体化学分配基于 X 射线 晶体结构测定和圆二色光谱测定。

  DOI：

  10.1071/c97088
• 作为产物：
  描述：

  1(3H)-Isobenzofuranone, 4,7-dimethoxy-3-(phenylsulfonyl)- 在 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 6.67h， 生成 1,4,5,8-tetramethoxy-naphthalene-2-carbonitrile
  参考文献：
  名称：

  A New Efficient Route for Multigram Asymmetric Synthesis of Alkannin and Shikonin

  摘要：

  A short and convergent approach for the synthesis of alkannin, shikonin and shikalkin is presented. A Hauser-type annulation of cyanophthalide 26 with enone 7 affords the complete aromatic system in just one step with concomitant attachment of the entire side chain. Subsequent Corey's oxazaborolidine mediated asymmetric reduction of the above advanced intermediate, leads to the required isomer in high enantiomeric excess. Finally, a selective and high yielding deprotection protocol furnishes the title compounds as pure crystalline precipitates. Thus, a multigram synthesis of shikonin, alkannin and shikalkin is achieved in high yield and enantioselectivity.

  DOI：

  10.1002/1521-3765(20020415)8:8<1795::aid-chem1795>3.0.co;2-v

文献信息

• Monosubstituted Tetramethoxynaphthalenes
  作者：Yasuhiro Tanoue、Akira Terada、Kazuhiko Torisu、Hiroshige Taniguchi

  DOI：10.1246/bcsj.62.1211

  日期：1989.4.15

  As new intermediates for the syntheses of monosubstituted naphthazarins and anthracyclines, several tetramethoxynaphthalenes having a substituent such as CH3, COOH, CN, Br, OAc, OH, and OMe groups were prepared from 1,4,5,8-tetramethoxynaphthalene and 2-formyl-1,4,5,8-tetramethoxynaphthalene.

  作为合成单取代萘扎林和蒽环类化合物的新中间体，几种具有 CH3、COOH、CN、Br、OAc、OH 和 OMe 等取代基的四甲氧基萘被从 1,4,5,8-四甲氧基萘和 2-甲酰基-1,4,5,8-四甲氧基萘合成出来。
• Absolute stereochemistry of 1,2′-linked bi(naphthoquinone)s
  作者：Robert W. Baker、Song Liu、Melvyn V. Sargent、Brian W. Skelton、Allan H. White

  DOI：10.1039/a607720j

  日期：——

  Asymmetric syntheses of the enantiomers of the naturally occurring atropisomerically chiral 1,2′-linked bi(naphthoquinone)s 8′-hydroxyisodiospyrin and isodiospyrin have allowed their absolute configurations to be assigned by X-ray and circular dichroism spectral studies of synthetic intermediates.

  天然存在的1,2-联萘醌和对映异构体8-羟基异二氧呋喃和对二氧呋喃的非对称合成，使得它们的绝对构型可以通过合成中间体的X射线和圆二色光谱研究来确定。
• Asymmetric synthesis of alkannin and shikonin
  作者：Elias A. Couladouros、Zoi F. Plyta、Alexandros T. Strongilos、Vassilios P. Papageorgiou

  DOI：10.1016/s0040-4039(97)01687-0

  日期：1997.10

  A new general and convergent route for the synthesis of the title compounds is presented. The polyoxygenated aromatic ring system is annulated in one operation by the condensation of a Michael type acceptor with an 1,4 dipole equivalent. The chiral center of the target is introduced via an asymmetric allyl boration in high ee. Overall, the fully protected natural product is constructed within 8 steps in 35% total yield. (C) 1997 Elsevier Science Ltd.
• TANOUE, YASUHIRO;TERADA, AKIRA;TORISU, KAZUHIKO;TANIGUCHI, HIROSHIGE, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 1211-1214
  作者：TANOUE, YASUHIRO、TERADA, AKIRA、TORISU, KAZUHIKO、TANIGUCHI, HIROSHIGE

  DOI：——

  日期：——
• A New Efficient Route for Multigram Asymmetric Synthesis of Alkannin and Shikonin
  作者：Elias A. Couladouros、Alexandros T. Strongilos、Vassilios P. Papageorgiou、Zoi F. Plyta

  DOI：10.1002/1521-3765(20020415)8:8<1795::aid-chem1795>3.0.co;2-v

  日期：2002.4.15

  A short and convergent approach for the synthesis of alkannin, shikonin and shikalkin is presented. A Hauser-type annulation of cyanophthalide 26 with enone 7 affords the complete aromatic system in just one step with concomitant attachment of the entire side chain. Subsequent Corey's oxazaborolidine mediated asymmetric reduction of the above advanced intermediate, leads to the required isomer in high enantiomeric excess. Finally, a selective and high yielding deprotection protocol furnishes the title compounds as pure crystalline precipitates. Thus, a multigram synthesis of shikonin, alkannin and shikalkin is achieved in high yield and enantioselectivity.