2-(3-hydroxy-4-methoxyphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene | 111154-41-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 苯并菲啶生物碱
• 英文名称: 2-(3-hydroxy-4-methoxyphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene
• 英文别名: N-[6-(3-hydroxy-4-methoxyphenyl)benzo[f][1,3]benzodioxol-5-yl]-N-methylformamide
• CAS: 111154-41-7
• 化学式: C₂₀H₁₇NO₅
• 分子量: 351.359
• InChiKey: VFJNDSYWSMPMSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-hydroxy-4-methoxyphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene 在 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.17h， 生成 dihydroisoterihanine
  参考文献：
  名称：

  Studies on the chemical constituents of rutaceous plants. LXIV. Structural establishment of oxyterihanine, a phenolic benzo[c]phenanthridone alkaloid. Syntheses of phenolic benzo[c]phenanthridine alkaloids, terihanine and isoterihanine, and related compounds.

  摘要：

  oxyterihanine (2c) 是从台湾两面针 (Fagara nitida ROXB.) 中分离出来的一种新型酚类苯并[c]菲啶酮生物碱，其结构被确定为 8-羟基-9-甲氧基-5-甲基-2, 3-亚甲基二氧基苯并[c]菲啶-6 (5H) 1，通过与合成样品直接比较，合成样品衍生自 2- (4-异丙氧基-3-甲氧基苯基) -6, 7-亚甲基二氧基-3, 4-二氢萘-1 (2H) -酮 (8a) 通过图 3 和图 4 所示的合成顺序进行。 9-羟基-8-甲氧基-5-甲基-2, 3-亚甲基二氧基苯并[c] 菲啶-6 (5H) -酮还合成了[oxyisoterihanine (2d)]和两种酚季苯并[c]菲啶生物碱terihanine (1c) 和isoterihanine (1d)。

  DOI：

  10.1248/cpb.35.2717
• 作为产物：
  描述：

  cis-2-(3-isopropoxy-4-methoxyphenyl)-6,7-methylendioxy-1-(N-methylformamido)-1,2,3,4-tetrahydronaphthalene 在 硫酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 2.34h， 生成 2-(3-hydroxy-4-methoxyphenyl)-6,7-methylenedioxy-1-(N-methylformamido)naphthalene
  参考文献：
  名称：

  Studies on the chemical constituents of rutaceous plants. LXIV. Structural establishment of oxyterihanine, a phenolic benzo[c]phenanthridone alkaloid. Syntheses of phenolic benzo[c]phenanthridine alkaloids, terihanine and isoterihanine, and related compounds.

  摘要：

  oxyterihanine (2c) 是从台湾两面针 (Fagara nitida ROXB.) 中分离出来的一种新型酚类苯并[c]菲啶酮生物碱，其结构被确定为 8-羟基-9-甲氧基-5-甲基-2, 3-亚甲基二氧基苯并[c]菲啶-6 (5H) 1，通过与合成样品直接比较，合成样品衍生自 2- (4-异丙氧基-3-甲氧基苯基) -6, 7-亚甲基二氧基-3, 4-二氢萘-1 (2H) -酮 (8a) 通过图 3 和图 4 所示的合成顺序进行。 9-羟基-8-甲氧基-5-甲基-2, 3-亚甲基二氧基苯并[c] 菲啶-6 (5H) -酮还合成了[oxyisoterihanine (2d)]和两种酚季苯并[c]菲啶生物碱terihanine (1c) 和isoterihanine (1d)。

  DOI：

  10.1248/cpb.35.2717

文献信息

• Studies on the Chemical Constituents of Rutaceous Plants. Part LXIX. Cesium Fluoride-Mediated Claisen Rearrangement of Aryl Propargyl Ether. Exclusive Formation of 2-Methylarylfuran and Its Availability as a Masked Salicylaldehyde.
  作者：Hisashi ISHII、Tsutomu ISHIKAWA、Sunao TAKEDA、Satoshi UEKI、Masahiro SUZUKI

  DOI：10.1248/cpb.40.1148

  日期：——

  Claisen rearrangement of an aryl propargyl ether in the presence of CsF led to exclusive formation of 2-methylarylfuran in excellent yield. The result of a precise examination of the rearrangement is described. Satisfactory transformation of the 2-methylarylfuran to a salicylaldehyde derivative was achieved by stepwise oxidation. This combination of reactions serves as a useful method for regioselective introduction of a C1 unit at the ortho position of a phenol group.

  在 CsF 的存在下，芳基丙炔醚发生克莱森重排反应，生成了纯度极高的 2-甲基芳基呋喃。本文介绍了对该重排反应进行精确检验的结果。通过逐步氧化，2-甲基芳基呋喃令人满意地转化为水杨醛衍生物。这种反应组合是在苯酚基团的正交位置上区域选择性引入 C1 单元的有用方法。
• 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)。
• ISHII, HISASHI;CHEN, IH-SHENG;UEKI, SATOSHI;AKAIKE, MISAKO;ISHIKAWA, TSUT+, CHEM. AND PHARM. BULL., 35,(1987) N 7, 2717-2725
  作者：ISHII, HISASHI、CHEN, IH-SHENG、UEKI, SATOSHI、AKAIKE, MISAKO、ISHIKAWA, TSUT+

  DOI：——

  日期：——
• Studies on the chemical constituents of rutaceous plants. LXIV. Structural establishment of oxyterihanine, a phenolic benzo[c]phenanthridone alkaloid. Syntheses of phenolic benzo[c]phenanthridine alkaloids, terihanine and isoterihanine, and related compounds.
  作者：HISASHI ISHII、IH-SHENG CHEN、SATOSHI UEKI、MISAKO AKAIKE、TSUTOMU ISHIKAWA

  DOI：10.1248/cpb.35.2717

  日期：——

  The structure of oxyterihanine (2c), a new phenolic benzo [c] phenanthridone alkaloid which was isolated from Formosan Xanthoxylum nitidum (ROXB.) D. C. (Fagara nitida ROXB.), was established as 8-hydroxy-9-methoxy-5-methyl-2, 3-methylenedioxybenzo [c] phenanthridin-6 (5H) one by direct comparison with a synthetic specimen, which was derived from 2- (4-isopropoxy-3-methoxyphenyl) -6, 7-methylenedioxy-3, 4-dihydronaphthalen-1 (2H) -one (8a) through the synthetic sequence shown in Charts 3 and 4. 9-Hydroxy-8-methoxy-5-methyl-2, 3-methylenedioxybenzo [c] phenanthridin-6 (5H) -one [oxyisoterihanine (2d)] and two phenolic quaternary benzo [c] phenanthridine alkaloids, terihanine (1c) and isoterihanine (1d), were also synthesized.

  oxyterihanine (2c) 是从台湾两面针 (Fagara nitida ROXB.) 中分离出来的一种新型酚类苯并[c]菲啶酮生物碱，其结构被确定为 8-羟基-9-甲氧基-5-甲基-2, 3-亚甲基二氧基苯并[c]菲啶-6 (5H) 1，通过与合成样品直接比较，合成样品衍生自 2- (4-异丙氧基-3-甲氧基苯基) -6, 7-亚甲基二氧基-3, 4-二氢萘-1 (2H) -酮 (8a) 通过图 3 和图 4 所示的合成顺序进行。 9-羟基-8-甲氧基-5-甲基-2, 3-亚甲基二氧基苯并[c] 菲啶-6 (5H) -酮还合成了[oxyisoterihanine (2d)]和两种酚季苯并[c]菲啶生物碱terihanine (1c) 和isoterihanine (1d)。