methyl 2-[2-hydroxy-2-(3,4,5-trimethoxyphenyl)-1-tosylethyl]-N-methoxymethylpyrrole-4-carboxylate | 647864-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-[2-hydroxy-2-(3,4,5-trimethoxyphenyl)-1-tosylethyl]-N-methoxymethylpyrrole-4-carboxylate
• 英文别名: methyl 2-[2-hydroxy-2-(3,4,5-trimethoxyphenyl)-1-tosylethyl]-N-methoxymethyl-4-pyrrolcarboxylate；Methyl 5-[2-hydroxy-1-(4-methylphenyl)sulfonyl-2-(3,4,5-trimethoxyphenyl)ethyl]-1-(methoxymethyl)pyrrole-3-carboxylate
• CAS: 647864-38-8
• 化学式: C₂₆H₃₁NO₉S
• 分子量: 533.599
• InChiKey: LHGAHVVMYAVJBR-UHFFFAOYSA-N

物化性质

• 熔点：
  175-177 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  698.8±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2-[2-hydroxy-2-(3,4,5-trimethoxyphenyl)-1-tosylethyl]-N-methoxymethylpyrrole-4-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯苯 为溶剂， 以100%的产率得到methyl N-methoxymethyl-2-[2-oxo-2-(3,4,5-trimethoxyphenyl)-1-tosylethyl]pyrrole-4-carboxylate
  参考文献：
  名称：

  通过在中央双键上包含甲苯磺酰基的对苯二酚的光环化反应制备菲。菲和菲咯啉类化合物合成的通用方法

  摘要：

  我们已经通过在氧化剂存在下紫外线照射对苯二酚对菲的经典制备方法进行了有用的修饰。该修饰涉及在碱的存在下辐照具有连接至中心双键的磺酰基的丁二烯。我们已经证明，该协议可以成功地应用于各种菲和菲类化合物的合成。

  DOI：

  10.1021/jo100742e
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 methyl 1-methoxymethyl-5-tosylmethyl-1H-pyrrole-3-carboxylate 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以88%的产率得到methyl 2-[2-hydroxy-2-(3,4,5-trimethoxyphenyl)-1-tosylethyl]-N-methoxymethylpyrrole-4-carboxylate
  参考文献：
  名称：

  通过在中央双键上包含甲苯磺酰基的对苯二酚的光环化反应制备菲。菲和菲咯啉类化合物合成的通用方法

  摘要：

  我们已经通过在氧化剂存在下紫外线照射对苯二酚对菲的经典制备方法进行了有用的修饰。该修饰涉及在碱的存在下辐照具有连接至中心双键的磺酰基的丁二烯。我们已经证明，该协议可以成功地应用于各种菲和菲类化合物的合成。

  DOI：

  10.1021/jo100742e

文献信息

• Areno [E]indols, preparation method and application as intermediates in
  申请人：Pharma-Mar, S.A.- Pharmar

  公开号：US05571927A1

  公开（公告）日：1996-11-05

  The areno[e]indols have the formula (I). The methods comprises: (a) reacting (VI) with an aldehyde Ar"--CHO to obtain (VII); (b) oxidizing (VII) to yield the cetone (VIII); (c) reating (VIII) with a strong base and thereafter with an acycle chloride ClCOR, to produce (IX); (d) subjecting to a photochemical cyclization (IX) to produce (I). In said formulas Ar is phenyl or substituted phenyl; Ar' is radical (i) or (ii); R is an acyle group, Ar" is a phenyl, pyrolyl, furanyl or thiophenyl group substituted up to three times by any of the radials R, R.sup.1, R.sup.2, or R.sup.3. The compounds (I) are useful as intermediates in the synthesis of hexahydroareno(e)cyclopropa(c)indol-4-ones with antitumoral activity.

  The areno[e]indols have the formula (I). The methods comprises: (a) reacting (VI) with an aldehyde Ar"--CHO to obtain (VII); (b) oxidizing (VII) to yield the cetone (VIII); (c) reating (VIII) with a strong base and thereafter with an acycle chloride ClCOR, to produce (IX); (d) subjecting to a photochemical cyclization (IX) to produce (I). In said formulas Ar is phenyl or substituted phenyl; Ar' is radical (i) or (ii); R is an acyle group, Ar" is a phenyl, pyrolyl, furanyl or thiophenyl group substituted up to three times by any of the radials R, R.sup.1, R.sup.2, or R.sup.3. The compounds (I) are useful as intermediates in the synthesis of hexahydroareno(e)cyclopropa(c)indol-4-ones with antitumoral activity.
• Base-Induced Photocyclization of 1,2-Diaryl-1-tosylethenes. A Mechanistically Novel Approach to Phenanthrenes and Phenanthrenoids
  作者：Jesús F. Almeida、Luis Castedo、Dolores Fernández、Ana G. Neo、Víctor Romero、Gabriel Tojo

  DOI：10.1021/ol0357954

  日期：2003.12.1

  phenanthrenes and heterocyclic analogues. These results are consistent with a mechanism involving the base-induced elimination of p-toluenesulfinic acid from an intermediate 9-tosyl-4a,4b-dihydrophenanthrene, formed by photochemical cyclization of the starting 1,2-diaryl-1-tosylstilbenes. [reaction: see text]

  在碱的存在下，用紫外光照射许多1,2-二芳基-1-甲苯磺基苯甲酸酯，得到相应的菲和杂环类似物。这些结果与一种机理有关，该机理涉及从中间体9-甲苯基-4a，4b-二氢菲中碱诱导的对甲苯磺酸的消除，该中间体是通过对起始的1,2-二芳基-1-甲苯磺基苯进行光化学环化而形成的。[反应：看文字]
• NEW ARENO[e]INDOLS, PREPARATION METHOD AND APPLICATION AS INTERMEDIATES IN THE SYNTHESIS OF PRODUCTS WITH ANTITUMORAL ACTIVITY
  申请人：PHARMA-MAR S.A.-PHARMAR

  公开号：EP0623619A1

  公开（公告）日：1994-11-09

  The areno(e)indols have the formula (I). The methods comprises: (a) reacting (VI) with an aldehyde Ar''-CHO to obtain (VII); (b) oxidizing (VII) to yield the cetone (VIII); (c) reating (VIII) with a strong base and thereafter with an acyle chloride CICOR, to produce (IX); (d) subjecting to a photochemical cyclization (IX) to produce (I). In said formulas Ar is phenyl or substituted phenyl; Ar' is a radical (i) or )ii); R is an acyle group, Ar'' is a phenyl, pyrolyl, furanyl or thiophenyl group substituted up to three times by any of the radicals R, R¹, R², or R³. The compounds (I) are useful as intermediates in the synthesis of hexahydroareno(e)cyclopropa(c)indol-4-ones with antitumoral activity.

  壬(e)吲哚具有式(I)。方法包括：(a) (VI) 与醛 Ar''-CHO 反应，得到 (VII)；(b) 氧化 (VII)，得到酮 (VIII)；(c) (VIII) 与强碱再反应，然后与酰基氯 CICOR 反应，得到 (IX)；(d) 对 (IX) 进行光化学环化反应，得到 (I)。在上述式子中，Ar 是苯基或取代苯基；Ar'是基(i)或)ii)；R 是酰基，Ar''是被 R、R¹、R² 或 R³ 中的任一基取代最多三次的苯基、吡咯基、呋喃基或噻吩基。化合物 (I) 可用作合成具有抗肿瘤活性的六氢areno(e)cyclopropa(c)indol-4-酮的中间体。
• Photocyclization of Tosylstilbenes as a Key Reaction in the Preparation of an Analogue of the Antitumor Agent CC-1065
  作者：Ana G. Neo、Antonio Pérez、Carmen López、Luis Castedo、Gabriel Tojo

  DOI：10.1021/jo900140t

  日期：2009.4.17

  A photocyclization of tosylstilbenes in the presence of base is used as a key reaction in the synthesis of the CC-1065 analogue 5.
• PREPARATION METHOD OF ARENO[e]INDOLS
  申请人：PHARMA-MAR S.A.-PHARMAR

  公开号：EP0623619B1

  公开（公告）日：1999-02-03