1,3-dimethyl-1H-naphtho[2,3-c]pyrane-5,10-dione | 215954-68-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 英文名称: 1,3-dimethyl-1H-naphtho[2,3-c]pyrane-5,10-dione
• 英文别名: 1,3-dimethyl-1H-naphtho[2,3-c]pyran-5,10-dione；1,3-dimethylbenzoisochromenequinone；1,3-dimethylpentalongin；1,3-dimethyl-1H-benzo[g]isochromene-5,10-dione
• CAS: 215954-68-0
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: FJVLRRSQCUZZHO-UHFFFAOYSA-N

物化性质

• 熔点：
  74-75 °C
• 沸点：
  408.6±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-1H-naphtho[2,3-c]pyrane-5,10-dione 在 三乙基硅烷 作用下， 以 三氟乙酸 为溶剂， 以98%的产率得到(+)-(1R,3S)-1,3-dimethyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-5,10-dione
  参考文献：
  名称：

  One-pot preparation of 1H-naphtho[2,3-c]pyran-5,10-diones and its application to concise total synthesis of (±)-eleutherin and (±)-isoeleutherin

  摘要：

  1H-Naphtho[2,3-c]pyran-5,10-dione derivatives, including a natural product (pentalongin), were generally synthesized in one-pot using a tandem conjugate addition-cyclization sequence between 2-(1-hydroxyalkyl)-1,4-naphthoquinones and enamines (or imines). The utility of this method was demonstrated in the synthesis of pyranonaphthoquinone antibiotics, (+/-)-eleutherin and (+/-)-isoeleutherin. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01683-9
• 作为产物：
  描述：

  1,4-二甲氧基-2-(1-羟基乙基)萘 在 ammonium cerium(IV) nitrate 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 2.5h， 生成 1,3-dimethyl-1H-naphtho[2,3-c]pyrane-5,10-dione
  参考文献：
  名称：

  1,3-二取代萘[2,3 - c ]吡喃-5,10-二酮的合成

  摘要：

  合成1,3-二取代的萘并[2,3 - c ]吡喃-5,10-二酮的两种简便方法是将酰基甲基引入2-（1-羟乙基）-1,4-开发了萘醌和随后的碱和酸诱导的闭环。

  DOI：

  10.1016/s0040-4020(01)00307-6

文献信息

• An efficient method for the one-pot construction of the 1H-naphtho[2,3-c]pyran-5,10-dione system
  作者：Kazuhiro Kobayashi、Masaharu Uchida、Tomokazu Uneda、Keiichi Yoneda、Miyuki Tanmatsu、Osamu Morikawa、Hisatoshi Konishi

  DOI：10.1039/b106933k

  日期：2001.11.15

  2-(1-Hydroxyalkyl)-1,4-naphthoquinones are found to react with pyrrolidino enamines in toluene to give 1H-naphtho[2,3-c]pyran-5,10-diones in good yields via a tandem conjugate addition–cyclization sequence, followed by an elimination of pyrrolidine. 2-Hydroxymethyl-1,4-naphthoquinone and morpholino enamines undergo a similar sequence, without loss of morpholine, to yield 3-morpholino-3,4-dihydro-1H-naphtho[2,3-c]pyran-5,10-diones. The 3-morpholino group of these products can be replaced with a hydro, a hydroxy, or a methoxy group. Imines also react with 2-(1-hydroxyalkyl)-1,4-naphthoquinones to give the corresponding 1H-naphtho[2,3-c]pyran-5,10-diones, including a natural product (pentalongin). The utility of these reactions is demonstrated in the synthesis of pyranonaphthoquinone antibiotics, viz. (±)-eleutherin and (±)-isoeleutherin.

  2-(1-羟基烷基)-1,4-萘醌与吡咯烯胺在甲苯中反应，通过串联的共轭加成-环化序列，高产率地生成1H-萼[2,3-c]吡喃-5,10-二酮，随后排除吡咯啉。2-羟基甲基-1,4-萘醌与吗啉烯胺经历类似的反应序列，且不损失吗啉，生成3-吗啉基-3,4-二氢-1H-萼[2,3-c]吡喃-5,10-二酮。这些产物的3-吗啉基可以被羟基、氢或甲氧基取代。亚胺也与2-(1-羟基烷基)-1,4-萘醌反应，生成对应的1H-萼[2,3-c]吡喃-5,10-二酮，包括一种天然产物（pentlongin）。这些反应的实用性在于合成了吡喃萘醌抗生素，如(±)-eleutherin和(±)-isoeleutherin。
• Total Synthesis of Two Naphthoquinone Antibiotics, Psychorubrin and Pentalongin, and Their C(1)-Substituted Alkyl and Aryl Derivatives
  作者：Bart Kesteleyn、Norbert De Kimpe、Luc Van Puyvelde

  DOI：10.1021/jo9811975

  日期：1999.2.1

  The synthesis of 1-alkyl- and 1-aryl-1H-naphtho[2,3-c]pyran-5,10-dione bearing a C(3)-C(4) double bond, was performed by two alternative cyclization strategies of 2,3-disubstituted 1,4-naphthoquinones. Lemieux-Johnson oxidation of 2-allyl-3-hydroxymethyl-1,4-dimethoxynaphthalenes and subsequent oxidative demethylation of the intermediate 3,4-dihydro-5,10-dimethoxy-1H-naphtho[2,3 -c]pyran-3-oles to the corresponding 3,4-dihydro-3-hydroxy-1H-naphtho[2,3-c]pyran-5, 10-diones gave, after acid-catalyzed dehydration, the de shed 1H-naphtho[2,3-c]pyran-5,10-diones. Alternatively, the pyranonaphthoquinone ring system was constructed by intramolecular acid-catalyzed condensation of(3-hydroxymethyl-1,4-naphthoquinone-2-yl)acetaldehyde acetals. Using this synthetic approach, the synthesis of two naturally occurring naphthoquinone antibiotics, pentalongin and psychorubrin, is reported.
• Isochromenes and their quinones through cyclisations with bisacetonitriledichloropalladium(II)
  作者：Robin G.F. Giles、Ivan R. Green、C.Peter Taylor

  DOI：10.1016/s0040-4039(99)00899-0

  日期：1999.6

  Bisacetonitriledichloropalladium(II) is found to cyclise ortho-alkenylbenzyl alcohols rapidly to the corresponding isochromenes. The reaction also proceeds rapidly for a 2-allyl-3-hydroxyalkyl-1,4-naphthoquinon when the product is a benzoisochromenequinone. (C) 1999 Elsevier Science Ltd. All rights reserved.

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