benzaldehyde O-{1-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-yl}oxime | 1388624-38-1

• 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: benzaldehyde O-{1-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-yl}oxime
• 英文别名: (E)-1-phenyl-N-[1-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-ynoxy]methanimine
• CAS: 1388624-38-1
• 化学式: C₂₃H₁₆F₃NO
• 分子量: 379.381
• InChiKey: ZOFGSSRCKCCMOP-WPWMEQJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzaldehyde O-{1-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-yl}oxime 在 盐酸 、 copper(l) iodide 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-benzyl 2-phenylvinyl-4-trifluoromethylphenylnitrone
  参考文献：
  名称：

  铜催化重排高效合成N-烷基化的α，β-不饱和酮硝酮

  摘要：

  使用铜催化剂从炔丙基氧胺有效地合成了N-烷基化的不饱和酮硝基。机理研究表明，重排反应是通过Cu催化的分子内加氢胺化反应进行的，随后是热诱导的电环开环反应。

  DOI：

  10.1021/ol501889g
• 作为产物：
  描述：

  1-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-ol 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 benzaldehyde O-{1-phenyl-3-[4-(trifluoromethyl)phenyl]prop-2-yn-1-yl}oxime
  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 1,6-dihydropyrimidines via copper-catalyzed multistep cascade reactions between O-propargylic aldoximes and isocyanates
  作者：Itaru Nakamura、Toshiki Onuma、Dong Zhang、Masahiro Terada

  DOI：10.1016/j.tetlet.2013.12.105

  日期：2014.2

  Multi-step cascade reactions of O-propargylic oximes with isocyanates were carried out in the presence of copper catalysts to afford the corresponding 1,6-dihydropyrimidines in good yields. The multi-step reactions consisted of a 2,3-rearrangement, a [3+2] cycloaddition, decarboxylative ring opening involving a 1,4-hydrogen shift, and a 6π-electrocyclization.

  在铜催化剂的存在下进行O-炔丙基肟与异氰酸酯的多步级联反应，以高收率得到相应的1，6-二氢嘧啶。该多步骤反应包括2，3-重排，[3 + 2]环加成，涉及1，4-氢移位的脱羧开环和6π-电环化。
• Copper-Catalyzed Skeletal Rearrangement of O-Propargylic Aryloximes into Four-Membered Cyclic Nitrones - Chirality Transfer and Mechanistic Insight
  作者：Itaru Nakamura、Yu Kudo、Toshiharu Araki、Dong Zhang、Eunsang Kwon、Masahiro Terada

  DOI：10.1055/s-0031-1290819

  日期：2012.5

  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.
• Efficient Synthesis of <i>N-</i>Alkylated α,β-Unsaturated Ketonitrones via Cu-Catalyzed Rearrangement
  作者：Itaru Nakamura、Toshiki Onuma、Ryo Kanazawa、Yuki Nishigai、Masahiro Terada

  DOI：10.1021/ol501889g

  日期：2014.8.15

  N-Alkylated unsaturated ketonitrones were efficiently synthesized from propargyloxyamines using Cu catalysts. Mechanistic studies suggest that the rearrangement reaction proceeds via Cu-catalyzed intramolecular hydroamination, followed by thermally induced electrocyclic ring opening.

  使用铜催化剂从炔丙基氧胺有效地合成了N-烷基化的不饱和酮硝基。机理研究表明，重排反应是通过Cu催化的分子内加氢胺化反应进行的，随后是热诱导的电环开环反应。