(Z)-N-benzylidene-2-methoxyaniline oxide | 1185154-36-2

• 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: (Z)-N-benzylidene-2-methoxyaniline oxide
• 英文别名: N-(2-methoxyphenyl)-1-phenylmethanimine oxide
• CAS: 1185154-36-2；178923-60-9
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: WRLBERYVJXAFRM-PTNGSMBKSA-N

物化性质

• 沸点：
  398.0±44.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-N-benzylidene-2-methoxyaniline oxide 、 (4-methoxybenzoyl)trimethylsilane 在 (R,R)-TADDOL-phosphite 、 lithium hexamethyldisilazane 作用下， 以 various solvent(s) 为溶剂， 反应 0.08h， 以77%的产率得到1-(4-methoxyphenyl)-2-(N-(2-methoxyphenyl)-N-trimethylsilyloxy)amino-2-phenylethanone
  参考文献：
  名称：

  Enantioselective Metallophosphite-Catalyzed C-Acylation of Nitrones

  摘要：

  Metallophosphites derived from tartaric acid catalyze the enantioselective addition of acyl silanes to nitrones. The product alpha N-silyloxyamino ketones are obtained in moderate to good yields (36-94%) with excellent enantioselectivity (er >= 95:5). The nitrone oxygen is essential in facilitating the silyl transfer that is required for catalyst turnover. This represents, to the best of our knowledge, the first example of C-acylation of nitrones and the most highly enantioselective catalytic addition of an acyl anion equivalent to an azomethine electrophile. The N-O bond of the product may be reductively cleaved under mild conditions to provide N- aryl alpha-amino ketones with negligible loss of enantiopurity.

  DOI：

  10.1021/ja076095n
• 作为产物：
  描述：

  2-硝基苯甲醚 、 苯甲醛 在 氯化铵 、 锌 作用下， 以 乙醇 、 水 为溶剂， 以48%的产率得到(Z)-N-benzylidene-2-methoxyaniline oxide
  参考文献：
  名称：

  An Asymmetric Hetero-Claisen Approach to 3-Alkyl-3-aryloxindoles

  摘要：

  The reaction of a chiral N-phenylnitrone derived from Garner's aldehyde with alkylarylketenes generates 3-alkyl-3-aryloxindoles directly in excellent yields and with good to excellent levels of enantioselectivity (up to 90% ee).

  DOI：

  10.1021/ol901441t

文献信息

• SPIRO DERIVATIVES OF PARTHENIN AS NOVEL ANTICANCER AGENTS
  申请人：Council Of Scientific & Industrial Research

  公开号：EP2265620A1

  公开（公告）日：2010-12-29
• Spiro Derivatives of Parthenin as Novel Anticancer Agents
  申请人：Halmuthur Mahabalarao Sampath Kumar

  公开号：US20110201661A1

  公开（公告）日：2011-08-18

  The present invention relates to novel spiro derivatives of parthenin prepared by the dipolar cycloaddition of various dipoles viz, benzonitrile oxides, nitrones, azides, nitrile ylide diazoalkane, nitrile imide, ozone, azomethine imides, azomethine ylides etc. with exocyclic double bond of C ring (α-methylene-γ-butyrolactone). Representative compounds have been screened for their anticancer activity against different cancer cell lines. ICs0 value of these analogues varies between 4.3 μM to 93 μM. A mechanistic correlation of their anticancer activity has been described. The results of the cytotoxicity test of the compounds studies indicated that the α,β-unsaturated ketonic moiety in parthenin plays an important role in the maintenance of the high level of cytotoxicity.
• US4153722A
  申请人：——

  公开号：US4153722A

  公开（公告）日：1979-05-08
• US4197314A
  申请人：——

  公开号：US4197314A

  公开（公告）日：1980-04-08
• US4214003A
  申请人：——

  公开号：US4214003A

  公开（公告）日：1980-07-22