O-(3-cyclohexyl-1-phenylprop-2-yn-1-yl)hydroxylamine | 1228682-71-0

• 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: O-(3-cyclohexyl-1-phenylprop-2-yn-1-yl)hydroxylamine
• CAS: 1228682-71-0
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: BRQSHCUIVYVAQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-cyclohexyl-1-phenylprop-2-yn-1-yl)hydroxylamine 、 苯甲醛 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 benzaldehyde O-(3-cyclohexyl-1-phenylprop-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
• 作为产物：
  描述：

  3-cyclohexyl-1-phenylprop-2-yn-1-ol 在 N-羟基邻苯二甲酰亚胺 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 O-(3-cyclohexyl-1-phenylprop-2-yn-1-yl)hydroxylamine
  参考文献：
  名称：

  铜催化未活化的异戊烯系的O-丙炔肟的环化异构反应：合成六氢吡咯并[3,4- b ] azepin-5（4 H）-ones的多米诺反应序列

  摘要：

  已开发了一种新型的铜催化的未活化的丙二烯系的O-炔丙基肟肟化的环异构体，用于合成六氢吡咯并[3,4- b ] azepin-5（4 H）-ones。一锅多米诺反应通过[2,3]-σ重排，[3 + 2]环加成和另一个[3,3]-σ重排进行。该方法为在无环前体中同时形成四个新键（一个C═O，一个C═N和两个CC键）快速组装来自无环前体的稠合双环基序的两个环成分提供了一条实用而直接的途径。一小步。

  DOI：

  10.1021/acs.orglett.1c00837

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）。
• Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides
  作者：Itaru Nakamura、Dong Zhang、Masahiro Terada

  DOI：10.1016/j.tetlet.2011.09.107

  日期：2011.11

  (Z)-Propargylic oxime ethers derived from alpha,beta-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rearrangement, 4 pi electrocyclization, and ring expansion. (C) 2011 Elsevier Ltd. All rights reserved.
• Copper-Catalyzed Tandem [2,3]-Rearrangement and 6π-3-Azatriene Electrocyclization in (<i>E</i>)<i>-O</i>-Propargylic α,β-Unsaturated Oximes
  作者：Itaru Nakamura、Dong Zhang、Masahiro Terada

  DOI：10.1021/ja102436z

  日期：2010.6.16

  Cu-catalyzed cyclizations of (E)-O-propargylic oximes of alpha,B-unsaturated aldehydes were successfully carried out to afford the corresponding pyridine oxides in good to high yields. As an example, (E)-acrylaldehyde O-1,3-diphenylprop-2-ynyl oxime (1b) was reacted for 5 h in the presence of CuBr(PPh(3))(3) (10 mol %) and PPh(3) (10 mol %) in DMSO at 120 degrees C to afford 3-benzyl-2-phenylpyridine-N-oxide (2b) in 84% yield. In this case, the reaction proceeded via Cu-catalyzed propargyl oxime-allenyl nitrone rearrangement followed by 6 pi-3-azatriene electrocyclization.