N-(4-nitrobenzenesulfonyl)-2-(4-methoxyphenyl)ethylamine | 114727-27-4

• 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: N-(4-nitrobenzenesulfonyl)-2-(4-methoxyphenyl)ethylamine
• 英文别名: N-4-nitrobenzenesulfonyl-4-methoxyphenethylamine；N-[2-(4-Methoxyphenyl)ethyl]-4-nitrobenzenesulphonamide；N-[2-(4-methoxyphenyl)ethyl]-4-nitrobenzenesulfonamide
• CAS: 114727-27-4
• 化学式: C₁₅H₁₆N₂O₅S
• mdl: MFCD01350824
• 分子量: 336.368
• InChiKey: QCOVAPJIFGOZQP-UHFFFAOYSA-N

物化性质

• 熔点：
  105.9-106.8 °C
• 沸点：
  528.1±60.0 °C(predicted)
• 密度：
  1.329±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-nitrobenzenesulfonyl)-2-(4-methoxyphenyl)ethylamine 在 palladium diacetate 乙酸酐 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 22.0h， 生成 acetic acid 3-[[2-(4-metyhoxyphenyl)ethyl]-(4-nitrobenzenesulfonyl)amino]allyl ester
  参考文献：
  名称：

  催化N-磺酰亚胺离子介导的α-乙烯基取代的异喹啉和β-咔啉的环化及其在复分解中的应用

  摘要：

  催化Sn（OTf）2诱导的线性，含芳基的烯丙基N，O-乙缩醛的环化反应生成乙烯基取代的四氢异喹啉和四氢-1 H -β-咔啉。乙烯基部分在所得产物中的有用性通过生物碱结构的各种关键结构单元的合成得到证明。α-乙烯基部分用于[2,3]σ重排，闭环置换和基于交叉复分解的长春瑞特，抗缺氧剂和长春胺型天然产物的合成成员的合成。

  DOI：

  10.1021/jo050503t
• 作为产物：
  描述：

  N-(对硝基苯磺酰基)氮杂环丙烷 、 4-甲氧基苯硼酸 在 3-氯苯酚 、 三(1-萘基)膦 、 caesium carbonate 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以94%的产率得到N-(4-nitrobenzenesulfonyl)-2-(4-methoxyphenyl)ethylamine
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of N-Sulfonylaziridines with Boronic Acids

  摘要：

  A mild palladium-catalyzed cross-coupling of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is presented. The reaction is highly regioselective and compatible with diverse functionality. A catalytic amount of base, a sterically demanding triarylphosphine ligand, and a phenol additive are critical to the success of the reaction. Coupling of a deuterium-labeled substrate established that ring opening of the aziridine occurs with inversion of stereochemistry.

  DOI：

  10.1021/ja410686v

文献信息

• 5-Aminosulphoryl substituted indole derivatives
  申请人：Glaxo Group Limited

  公开号：US04876267A1

  公开（公告）日：1989-10-24

  Indole derivatives are disclosed of the formula (I): ##STR1## wherein R.sub.1 represents H, or C.sub.1-6 alkyl or C.sub.3-6 Alkenyl; R.sub.2 represents a H, C.sub.1-3 alkyl, C.sub.3-6 alkenyl or C.sub.5-7 cycloalkyl, or a phenyl or phen(C.sub.1-4)alkyl group in which the phenyl ring is optionally substituted by halogen or C.sub.1-3 alkyl, C.sub.1-3 alkoxy or hydroxyl, or by a group NR.sup.a R.sup.b, or CONR.sup.a R.sup.b, wherein R.sup.a and R.sup.b each independently represents H or C.sub.1-3 alkyl; R.sub.3 and R.sub.4, each independently represents H or C.sub.1-3 alkyl or 2-propenyl; and physiologically acceptable salts and solvates (e.g. hydrates) thereof. The compounds have potent and selective vasoconstrictor activity and are indicated as useful for the treatment of migraine. The compounds may be formulated as pharmaceutical compositions with pharmaceutically acceptable carriers or excipients for administration by any suitable means. Various methods for the preparation of the compounds are disclosed.

  本发明揭示了式（I）的吲哚衍生物：##STR1## 其中R.sub.1表示H，或C.sub.1-6烷基或C.sub.3-6烯基；R.sub.2表示H，C.sub.1-3烷基，C.sub.3-6烯基或C.sub.5-7环烷基，或苯基或苯（C.sub.1-4）烷基，其中苯环可选择地被卤素或C.sub.1-3烷基，C.sub.1-3烷氧基或羟基或由NR.sup.a R.sup.b或CONR.sup.a R.sup.b表示的基取代，其中R.sup.a和R.sup.b各自独立地表示H或C.sub.1-3烷基；R.sub.3和R.sub.4，各自独立地表示H或C.sub.1-3烷基或2-丙烯基；以及其生理上可接受的盐和溶剂（例如水合物）。这些化合物具有强大而选择性的血管收缩活性，并被指示用于治疗偏头痛。这些化合物可以与药物学上可接受的载体或赋形剂配制成药物组合物，以通过任何适当的方式进行给药。揭示了制备这些化合物的各种方法。
• Indole derivatives
  申请人：GLAXO GROUP LIMITED

  公开号：EP0254433A2

  公开（公告）日：1988-01-27

  Indole derivatives are disclosed of the formula wherein R₁ represents H, or C₁-₆ alkyl or C₃-₆ alkenyl; R₂ represents a H, C₁-₃ alkyl, C₃-₆ alkenyl or C₅-₇ cycloalkyl, or a phenyl or phen(C₁-₄)alkyl group in which the phenyl ring is optionally substituted by halogen or C₁-₃ alkyl, C₁-₃ alkoxy or hydroxyl, or by a group NRaRb, or CONRaRb, wherein Ra and Rb each independently represents H or C₁-₃ alkyl; R₃ and R₄, each independently represents H or C₁-₃ alkyl or 2-propenyl; and physiologically acceptable salts and solvates (e.g. hydrates) thereof. The compounds have potent and selective vasoconstrictor activity and are indicated as useful for the treatment of migraine. The compounds may be formulate as pharmaceutical compositions with pharmaceuticaly acceptable carriers or excipients for administration by any suitable means. Various methods for the preparation of the compounds are disclosed.

  公开了式中的吲哚衍生物 其中 R₁ 代表 H、C₁-₆ 烷基或 C₃-₆ 烯基； R₂ 代表 H、C₁-₃ 烷基、C₃-₆ 烯基或 C₅-₇ 环烷基，或苯基或苯基(C₁-₄)烷基，其中苯基环可任选被卤素或 C₁-₃ 烷基取代、C₁-₃烷氧基或羟基，或被基团 NRaRb 或 CONRaRb 取代，其中 Ra 和 Rb 各自独立地代表 H 或 C₁-₃ 烷基； R₃ 和 R₄ 各自独立地代表 H 或 C₁-₃ 烷基或 2-丙烯基； 及其生理上可接受的盐类和溶剂（如水合物）。 这些化合物具有强效的选择性血管收缩活性，可用于治疗偏头痛。这些化合物可与药物可接受的载体或赋形剂配制成药物组合物，以任何合适的方式给药。公开了制备这些化合物的各种方法。
• US4876267A
  申请人：——

  公开号：US4876267A

  公开（公告）日：1989-10-24
• Palladium-Catalyzed Cross-Coupling of <i>N</i>-Sulfonylaziridines with Boronic Acids
  作者：Megan L. Duda、Forrest E. Michael

  DOI：10.1021/ja410686v

  日期：2013.12.11

  A mild palladium-catalyzed cross-coupling of unsubstituted and 2-alkyl-substituted aziridines with arylboronic acid nucleophiles is presented. The reaction is highly regioselective and compatible with diverse functionality. A catalytic amount of base, a sterically demanding triarylphosphine ligand, and a phenol additive are critical to the success of the reaction. Coupling of a deuterium-labeled substrate established that ring opening of the aziridine occurs with inversion of stereochemistry.
• Catalytic <i>N</i>-Sulfonyliminium Ion-Mediated Cyclizations to α-Vinyl-Substituted Isoquinolines and β-Carbolines and Applications in Metathesis
  作者：Sape S. Kinderman、Monique M. T. Wekking、Jan H. van Maarseveen、Hans E. Schoemaker、Henk Hiemstra、Floris P. J. T. Rutjes

  DOI：10.1021/jo050503t

  日期：2005.7.1

  vinyl moiety in the resulting products was demonstrated via the synthesis of various key building blocks for alkaloid structures. The α-vinyl moiety was utilized in a [2,3] sigmatropic rearrangement, in ring-closing metathesis and a cross-metathesis-based synthesis of vincantril, an antianoxia agent, and a synthetic member of the vincamine type natural products.

  催化Sn（OTf）2诱导的线性，含芳基的烯丙基N，O-乙缩醛的环化反应生成乙烯基取代的四氢异喹啉和四氢-1 H -β-咔啉。乙烯基部分在所得产物中的有用性通过生物碱结构的各种关键结构单元的合成得到证明。α-乙烯基部分用于[2,3]σ重排，闭环置换和基于交叉复分解的长春瑞特，抗缺氧剂和长春胺型天然产物的合成成员的合成。