O-(3-(4-chlorophenyl)-1-phenylprop-2-yn-1-yl)hydroxylamine | 1388625-00-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: O-(3-(4-chlorophenyl)-1-phenylprop-2-yn-1-yl)hydroxylamine
• CAS: 1388625-00-0
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: OARRCKVFZCRDPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.25
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  O-(3-(4-chlorophenyl)-1-phenylprop-2-yn-1-yl)hydroxylamine 在 copper(I) bromide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 26.0h， 生成 (4E)-4-benzylidene-1-(4-chlorophenyl)-3-phenylazetidin-2-one
  参考文献：
  名称：

  Copper-Catalyzed Skeletal Rearrangement of O-Propargylic Aryloximes into Four-Membered Cyclic Nitrones - Chirality Transfer and Mechanistic Insight

  摘要：

  Copper-catalyzed skeletal rearrangement of O-propargylic aryloximes (E)-1 were carried out to afford the corresponding four-membered cyclic nitrones 2 in good to excellent yields. The optimal reactions conditions of the highly regioselective reactions involved the use of [CuCl(cod)](2) in acetonitrile at 70 degrees C. In the case of (Z)-1, however, the reaction proceeded in the absence of the copper catalysts to afford the identical compound 2 in good yields. Furthermore, the reactions were also carried out using chiral substrates (R)-1 in the presence of Cu catalysts to afford (R)-2 with good levels of chirality transfer.

  DOI：

  10.1055/s-0031-1290819
• 作为产物：
  描述：

  在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 O-(3-(4-chlorophenyl)-1-phenylprop-2-yn-1-yl)hydroxylamine
  参考文献：
  名称：

  Copper-Catalyzed Skeletal Rearrangement of O-Propargylic Aryloximes into Four-Membered Cyclic Nitrones - Chirality Transfer and Mechanistic Insight

  摘要：

  Copper-catalyzed skeletal rearrangement of O-propargylic aryloximes (E)-1 were carried out to afford the corresponding four-membered cyclic nitrones 2 in good to excellent yields. The optimal reactions conditions of the highly regioselective reactions involved the use of [CuCl(cod)](2) in acetonitrile at 70 degrees C. In the case of (Z)-1, however, the reaction proceeded in the absence of the copper catalysts to afford the identical compound 2 in good yields. Furthermore, the reactions were also carried out using chiral substrates (R)-1 in the presence of Cu catalysts to afford (R)-2 with good levels of chirality transfer.

  DOI：

  10.1055/s-0031-1290819

文献信息

• Synthesis of Azepine Derivatives by Rhodium-Catalyzed Tandem 2,3-Rearrangement/Heterocyclization
  作者：Itaru Nakamura、Masashi Okamoto、Yoshinori Sato、Masahiro Terada

  DOI：10.1002/anie.201205285

  日期：2012.10.22

  Easy to N‐cycle: The efficient synthesis of azepine derivatives was achieved by Rh‐catalyzed tandem 2,3‐rearrangement involving the heterocyclization of N‐allenylnitrone intermediates (see scheme; cod=1,5‐cyclooctadiene, tppms=sodium diphenylphosphinobenzene‐3‐sulfonate).

  易于N循环：通过Rh催化的串联2,3重排涉及N-亚烯基硝烯中间体的杂环化，实现了氮杂衍生物的有效合成（参见方案; cod = 1,5-环辛二烯，tppms =二苯基膦基苯钠-3 -磺酸盐）。