3-羟基-3,4-二氢-1H-苯并[g]异苯并吡喃-5,10-二酮 | 110271-41-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 中文名称: 3-羟基-3,4-二氢-1H-苯并[g]异苯并吡喃-5,10-二酮
• 英文名称: Psychorubrin
• 英文别名: 3-Hydroxy-3,4-dihydro-1H-benzo[g]isochromene-5,10-dione
• CAS: 110271-41-5
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: REQISTGTAMMJHO-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C
• 沸点：
  469.1±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3-羟基-3,4-二氢-1H-苯并[g]异苯并吡喃-5,10-二酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.33h， 以81%的产率得到pentalongin
  参考文献：
  名称：

  抗肿瘤药。89. Psychorubrin，一种来自Psychotria rubra的新型细胞毒性萘醌，其构效关系良好。

  摘要：

  从Psychotria rubra的酒精提取物中分离出的新萘醌在KB细胞测定中表现出显着的细胞毒性（ED50 = 3.0微克/ mL）。光谱数据被用于将精神尿蛋白的结构指定为2。制备了萘醌衍生物6、8、13和14，并表现出比精神尿蛋白更好的细胞毒活性。所有这些都是潜在的迈克尔受体，其结合已扩展。然而，当此类化合物中存在亲水性羟基时，观察到体外活性降低。

  DOI：

  10.1021/jm00394a013
• 作为产物：
  描述：

  methyl (3-allyl-1,4-dimethoxynaphthalene-2-yl)carboxylate 在 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 ammonium cerium(IV) nitrate 作用下， 以 1,4-二氧六环 、 乙醚 、 水 、 乙腈 为溶剂， 反应 88.5h， 生成 3-羟基-3,4-二氢-1H-苯并[g]异苯并吡喃-5,10-二酮
  参考文献：
  名称：

  Total Synthesis of Two Naphthoquinone Antibiotics, Psychorubrin and Pentalongin, and Their C(1)-Substituted Alkyl and Aryl Derivatives

  摘要：

  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.

  DOI：

  10.1021/jo9811975

文献信息

• Simple Synthesis of Two Naphthoquinone Antibiotics Psychorubrin and Pentalongin
  作者：Vivek J. Bulbule、Priti S. Koranne、Yogesh S. Munot、Hanumant B. Borate、Vishnu H. Deshpande

  DOI：10.1081/scc-120015812

  日期：2003.1.4

  3-c]pyran-5,10-dione derivatives were synthesized using chloromethylation of substituted-2-naphthylacetic acid as the key step. The utility of this method was demonstrated in the synthesis of two-pyranonaphthoquinone antibiotics psychorubrin (1) and pentalongin (2).

  摘要 以取代-2-萘乙酸的氯甲基化反应为关键步骤，合成了1H-萘并[2,3-c]吡喃-5,10-二酮衍生物。这种方法的效用在双吡喃萘醌类抗生素精神红素 (1) 和五角糖素 (2) 的合成中得到了证明。
• Synthesis of pyranonaphthoquinone antibiotics involving the ring closing metathesis of a vinyl ether
  作者：Tuyen Nguyen Van、Norbert De Kimpe

  DOI：10.1016/j.tetlet.2004.03.008

  日期：2004.4

  The synthesis of two antibiotic pyranonaphthoquinones was performed by a straightforward synthetic route utilizing ring closing metathesis. Vinylation of 3-(1-propenyl)-2-hydroxymethyl-1.4-dimethoxynapthalene under iridium catalysis and subsequent ring closing metathesis of 3-(1-propenyl)-2-vinyloxymethyl-1.4-dimethoxynaphthalene with Grubbs' catalyst paved the way to the natural antibiotics pentalongin and psychorubrin. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of Two Naphthoquinone Antibiotics Pentalongin and Psychorubrin
  作者：Bart Kesteleyn

  DOI：10.1055/s-1999-3613

  日期：1999.11
• HAYASHI, TOSHIMITSU;SMITH, FORREST T.;LEE, KUO-HSIUNG, J. MED. CHEM., 30,(1987) N 11, 2005-2008
  作者：HAYASHI, TOSHIMITSU、SMITH, FORREST T.、LEE, KUO-HSIUNG

  DOI：——

  日期：——
• 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.