2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one | 130627-30-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one
• 英文别名: 6-(7-methoxy-2-methyl-1-benzofuran-4-yl)-7,8-dihydro-6H-benzo[f][1,3]benzodioxol-5-one
• CAS: 130627-30-4
• 化学式: C₂₁H₁₈O₅
• 分子量: 350.371
• InChiKey: JNUJGGFLRFNFDN-UHFFFAOYSA-N

物化性质

• 沸点：
  549.5±50.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one 在 2-甲基丁-1,3-二烯-1-醇乙酸酯 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-(methylenedioxy)-1-naphthol
  参考文献：
  名称：

  Structure and synthesis of arnottin I: a 6H-benzo[d]naphtho[1, 2-b]pyran-6-one derivative from a plant source

  摘要：

  Arnottin I 2 isolated from Xanthoxylum arnottianum Maxim and of previously unknown structure has been unambiguously synthesized utilizing a 2-methylarenofuran as a masked salicylaldehyde. This is the first occurrence of a 6H-benzo[d]naphtho[1,2-b]pyran-6-one derivative, the same skeleton as that of gilvocarsin-type antibiotics showing antitumour activity, from a plant source.

  DOI：

  10.1039/p19930001019
• 作为产物：
  描述：

  2-<4-(7-methoxy-2-methylbenzofuranyl)>-4-(3,4-methylenedioxyphenyl)-4-oxobutyronitrile 在 sodium hydroxide 、 氢气 、 potassium carbonate 、 甲烷 、 palladium dichloride 、 三氯氧磷 作用下， 以 乙醇 、 水 、 溶剂黄146 、 乙腈 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 6.5h， 生成 2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one
  参考文献：
  名称：

  Studies on the Chemical Constituents of Rutaceous Plants. Part LXXIII. Total Synthesis of Chelerythrine, a Benzo(c)phenanthridine Alkaloid.

  摘要：

  利用我们的新颖合成方法，包括CsF介导的芳基炔丙基醚克莱森重排为2-甲基苯并呋喃以及呋喃环氧化裂解为水杨醛，完成了苯并[c]菲啶生物碱白屈菜赤碱的全合成。通过图3所示的两条路线制备的共同中间体(5)。

  DOI：

  10.1248/cpb.40.2002

文献信息

• Cesium fluoride-mediated claisen rearrangement of aryl propargyl ether and its application to the synthesis of chelerythrine.
  作者：Hisashi ISHII、Tsutomu ISHIKAWA、Sunao TAKEDA、Satoshi UEKI、Masahiro SUZUKI、Takashi HARAYAMA

  DOI：10.1248/cpb.38.1775

  日期：——

  In the presence of cesium fluoride, the Claisen rearrangement of aryl propargyl ethers selectively provided 2-methylbenzofurans, which was successively treated with osmium tetroxide, periodic acid and 5% sodium hydroxide to give salicylaldehydes in good yields. The method was used to synthesize chelerythrine (2) via the common intermediate (8) prepared by the two routes as shown in Chart 3.

  在氟化铯存在下，芳基丙炔醚的克莱森重排选择性地提供了 2-甲基苯并呋喃，依次用四氧化锇、定期酸和 5%氢氧化钠处理后得到水杨醛，收率很高。如图 3 所示，该方法通过两种路线制备的共同中间体 (8) 合成了白屈菜红碱 (2)。
• Arnottin II, a unique spiro compound composed of a 3, 4-dehydro-1-tetralone and a phthalide skeleton: Is it biosynthetically related to a benzo[c]phenanthridine alkaloid ?
  作者：Tsutomu Ishikawa、Masayuki Murota、Toshiko Watanabe、Takashi Harayama、Hisashi Ishii

  DOI：10.1016/0040-4039(95)00757-4

  日期：1995.6

  The structure of arnottin II (2) was determined to be 3, 4-dehydro-6, 7-methylenedioxy-1-tetralone-2-spiro-3′-(6, 7-dimethoxyphthalide) by its synthesis. The exciton chirality method on the Cotton effects in the CD spectrum revealed the absolute stereochemistry as an R configuration. The biosynthetical relationship of 2 to chelerythrine (3), a benzo[c]phenanthridine alkaloid, is speculated.

  通过合成，确认了Arnottin II（2）的结构为3，4-脱氢-6，7-亚甲基二氧基-1-四氢萘-2-螺-3'-（6，7-二甲氧基邻苯二甲酸酯）。激子手性方法在CD光谱中对Cotton的影响揭示了R构型的绝对立体化学。推测了2与白屈菜红碱（3）的生物合成关系，白屈菜红碱为苯并[ c ]菲啶生物碱。
• Structure and synthesis of arnottin I: a 6H-benzo[d]naphtho[1, 2-b]pyran-6-one derivative from a plant source
  作者：Hisashi Ishii、Tsutomu Ishikawa、Masayuki Murota、Yoshiyuki Aoki、Takashi Harayama

  DOI：10.1039/p19930001019

  日期：——

  Arnottin I 2 isolated from Xanthoxylum arnottianum Maxim and of previously unknown structure has been unambiguously synthesized utilizing a 2-methylarenofuran as a masked salicylaldehyde. This is the first occurrence of a 6H-benzo[d]naphtho[1,2-b]pyran-6-one derivative, the same skeleton as that of gilvocarsin-type antibiotics showing antitumour activity, from a plant source.
• ISHII, HISASHI;ISHIKAWA, TSUTOMU;TAKEDA, SUNAO;UEKI, SATOSHI;SUZUKI, MASA+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 1775-1777
  作者：ISHII, HISASHI、ISHIKAWA, TSUTOMU、TAKEDA, SUNAO、UEKI, SATOSHI、SUZUKI, MASA+

  DOI：——

  日期：——
• Studies on the Chemical Constituents of Rutaceous Plants. Part LXXIII. Total Synthesis of Chelerythrine, a Benzo(c)phenanthridine Alkaloid.
  作者：Hisashi ISHII、Tsutomu ISHIKAWA、Sunao TAKEDA、Masahiro SUZUKI、Takashi HARAYAYA

  DOI：10.1248/cpb.40.2002

  日期：——

  By taking advantage of our novel synthetic methods involving CsF-mediated Claisen rearrangement of an aryl propargyl ether to a 2-methylbenzolfuran and oxidative cleavage of the furan ring to a salicylaldehyde, total synthesis of chelerythrine, a benzo[c]phenanthridine alkaloid, was accomplished via the common intermediate (5) prepared through the two routes shown in Chart 3.

  利用我们的新颖合成方法，包括CsF介导的芳基炔丙基醚克莱森重排为2-甲基苯并呋喃以及呋喃环氧化裂解为水杨醛，完成了苯并[c]菲啶生物碱白屈菜赤碱的全合成。通过图3所示的两条路线制备的共同中间体(5)。