2-(3,4-dimethoxyphenyl)-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one | 41303-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3,4-dimethoxyphenyl)-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 6-(3,4-dimethoxy-phenyl)-7,8-dihydro-6H-naphtho[2,3-d][1,3]dioxol-5-one；6-(3,4-Dimethoxy-phenyl)-7,8-dihydro-6H-naphtho[2,3-d][1,3]dioxol-5-on；6-(3,4-Dimethoxyphenyl)-7,8-dihydronaphtho[2,3-d][1,3]dioxol-5(6h)-one；6-(3,4-dimethoxyphenyl)-7,8-dihydro-6H-benzo[f][1,3]benzodioxol-5-one
• CAS: 41303-46-2
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: QDPCGSFBFKQHLN-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C(Solv: 1,4-dioxane (123-91-1); ethanol (64-17-5))
• 沸点：
  505.0±50.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one 在 sodium tetrahydroborate 、 四氯化钛 作用下， 生成 cis-2-(3,4-dimethoxyphenyl)-N-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydro-1-naphthylamine
  参考文献：
  名称：

  Ishii, Hisashi; Ishikawa, Tsutomu; Chen, Ih-Sheng, Heterocycles, 1984, vol. 21, # 2, p. 711

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 在 palladium on activated charcoal hydroxide 、 氢气 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙二醇乙醚 为溶剂， 生成 2-(3,4-dimethoxyphenyl)-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Ishii, Hisashi; Ishikawa, Tsutomu; Chen, Ih-Sheng, Heterocycles, 1984, vol. 21, # 2, p. 711

  摘要：

  DOI：

文献信息

• Studies on the chemical constituents of rutaceous plants. L. Development of a versatile method for the synthesis of antitumor-active benzo(c)phenanthridine alkaloids. 2. Preparation of 2-aryl-1-tetralone derivatives.
  作者：HISASHI ISHII、ERI KAWANABE、KENICHI HARADA、TAKEO DEUSHI、ETSUKO UEDA、TOSHIKO WATANABE、YUHICHIRO ICHIKAWA、MITSUGI SAKAMOTO、TOSHIAKI ISHIDA、TSUTOMU TAKAHASHI、KEIKO NAKAJIMA、TSUTOMU ISHIKAWA

  DOI：10.1248/cpb.31.3039

  日期：——

  The synthetic pathway from 2, 4-bisaryl-4-oxobutyramide (3) to 2-aryl-1-tetralone (4), which is the key intermediate in the Robinson synthesis of antitumor-active benzo [c] phenanthridine alkaloids was improved. Treatment of the model keto-amide (3a) under the reported basic conditions gave a γ-keto-α, β-unsaturated acid (9) and degradation products. Reduction of the 2, 4-bisaryl-4-oxobutyramide (3) with sodium borohydride gave 2, 4-bisaryl-4-hydroxybutyramide (16), which could easily be hydrogenolyzed to give 2, 4-bisarylbutyramide (15). However, this transformation also tended to give a γ-lactam derivative (17), unfortunately. We succeeded in the direct hydrogenolysis of the 2, 4-bisaryl-4-oxobutyramide (3) to the 2, 4-bisarylbutyramide (15), which could be hydrolyzed to the corresponding acid (5) without difficulty. The direct hydrolysis of the 2, 4-bisaryl-4-oxobutyronitrile (2) to the 2, 4-bisaryl-4-oxobutyric acid (6) as reported by Cheng et al. was also examined. Ten 2-aryl-1-tetralones (4) required as starting materials for syntheses of various benzo [c] phenanthridine alkaloids were prepared.

  从 2，4-二芳基-4-氧代丁酰胺（3）到 2-芳基-1-四氢萘酮（4）的合成途径得到了改进，而 2-芳基-1-四氢萘酮是罗宾逊合成具有抗肿瘤活性的苯并[c]菲啶生物碱的关键中间体。在报告的碱性条件下处理模型酮酰胺（3a），可得到γ-酮-α，β-不饱和酸（9）和降解产物。用硼氢化钠还原 2，4-双芳基-4-氧代丁酰胺（3），可得到 2，4-双芳基-4-羟基丁酰胺（16），很容易将其氢解，得到 2，4-双芳基丁酰胺（15）。然而，令人遗憾的是，这种转化也倾向于得到一种 γ-内酰胺衍生物（17）。我们成功地将 2，4-双芳基-4-氧代丁酰胺 (3) 直接氢解为 2，4-双芳基丁酰胺 (15)，后者可以顺利地水解为相应的酸 (5)。此外，还研究了 Cheng 等人报告的 2，4-二芳基-4-氧代丁腈（2）直接水解为 2，4-二芳基-4-氧代丁酸（6）的情况。制备了十种 2-芳基-1-四氢萘酮（4），作为合成各种苯并[c]菲啶生物碱的起始原料。
• Studies on the chemical constituents of rutaceous plants. LX. Development of a versatile method for syntheses of the antitumor benzo(c)phenanthridine alkaloids. 9. Efficient syntheses and antitumor activities of nitidine and related nonphenolic benzo(c)phenanthridine alkaloids.
  作者：HISASHI ISHII、YUHICHIRO ICHIKAWA、ERI KAWANABE、MUNEKAZU ISHIKAWA、TSUTOMU ISHIKAWA、KAZUO KURETANI、MOTOKO INOMATA、AKIO HOSHI

  DOI：10.1248/cpb.33.4139

  日期：——

  Several nonphenolic benzo [c] phenanthridine alkaloids including naturally occurring nitidine (1a) and avicine (1e) were synthesized in excellent yields through an efficient synthetic method developed by us. Antitumor activities of twelve alkaloids including four naturally occurring O5-alkaloids [chelilutine (1g), chelirubine (1h), sanguilutine (1k), and sanguirubine (11)] against Sarcoma 180 were tested. The structure-activity relationship of these alkaloids is discussed.

  几种非酚类的苯并[c]菲啶生物碱，包括自然存在的硝基啶（1a）和鬼针草碱（1e），通过我们开发的高效合成方法合成，产率极高。十二种生物碱的抗肿瘤活性进行了测试，包括四种自然存在的O5-生物碱 [chélilutine（1g）、chelirubine（1h）、sanguilutine（1k）和sanguirubine（11）] 对肉瘤180的活性。讨论了这些生物碱的结构-活性关系。
• 2-Aryl-1,4-naphthoquinone-1-oxime Methyl Ethers: Their Cytotoxic Activity
  作者：Tsutomu Ishikawa、Tatsuru Saito、Ayako Kurosawa、Toshiko Watanabe、Sakiko Maruyama、Yuh-ichiro Ichikawa、Ryota Yamada、Hiroko Okuzawa、Hiromi Sato、Koichi Ueno

  DOI：10.1248/cpb.59.472

  日期：——

  Preliminary examination for the structure–activity relationship of quinone monooxime derivatives on cytotoxicity against HeLa S3 cell and further trials using eight different cell lines suggested that 2-aryl-6,7-methylenedioxy-1,4-naphthoquinone-1-oxime methyl ethers, carrying 2-methoxy-4,5-methylenedioxyphenyl, 7-methoxy-2-methylbenzofuran-4-yl, and 2-methoxycarbonyl-3,4-dimethoxyphenyl as the 2-aryl substituent, were potential candidates for anti-cancer drugs.

  初步研究了醌单肟衍生物对 HeLa S3 细胞的细胞毒性的结构-活性关系，并使用八种不同的细胞系进行了进一步试验，结果表明，2-芳基-6,7-亚甲二氧基-1、4-萘醌-1-肟甲基醚，以 2-芳基取代基为 2-甲氧基-4,5-亚甲二氧基苯基、7-甲氧基-2-甲基苯并呋喃-4-基和 2-甲氧基羰基-3,4-二甲氧基苯基，是潜在的候选抗癌药物。
• Gopinath et al., Journal of the Chemical Society, 1959, p. 4012
  作者：Gopinath et al.

  DOI：——

  日期：——
• 804. An examination of the rutaceae of Hong Kong. Part IV. The synthesis of dihydronitidine
  作者：H. R. Arthur、Y. L. Ng

  DOI：10.1039/jr9590004010

  日期：——