1-naphthylacetaldoxime | 31125-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-naphthylacetaldoxime
• 英文别名: naphthylacetaldoxime；(Naphthyl-1)-acetaldehyd-oxim；α-Naphthyl-acetaldehyd-oxim；[1]naphthyl-acetaldehyde-oxime；α-Naphthylacetaldoxim；[1]Naphthyl-acetaldehyd-oxim；N-[2-(Naphthalen-1-yl)ethylidene]hydroxylamine；N-(2-naphthalen-1-ylethylidene)hydroxylamine
• CAS: 31125-58-3
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: PRHYOZSIYBXSIE-UHFFFAOYSA-N

物化性质

• 沸点：
  384.5±21.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-naphthylacetaldoxime 在 镍 吡啶 、 sodium hypochlorite 、 水 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.5h， 生成 4-Hydroxy-1,5-dinaphthalen-1-ylpentan-2-one
  参考文献：
  名称：

  3-Unsubstituted 1,5-Diaryl-2,4-pentanediones and -4-methoxy-2-pentanones:  Synthesis via Corresponding 3-Hydroxy Ketones Generated from 2-Isoxazolines

  摘要：

  Aryl acetaldoximes are reacted with allylarenes in the presence of sodium hypochlorite to give 3,5-bis(arylmethyl)-2-isoxazolines which are then converted to 1,5-diaryl-4-hydroxy-2-pentanones by a reductive hydrogenation in the presence of water. These intermediate aldols can then be either oxidized with Corey-Kim reagent to stable dimethylsulfonium 1-(arylacetyl)-2-oxo-3-arylpropylides followed by zinc-acetic acid reduction to give 1,5-diaryl-2,4-pentanediones, or converted to 1,5-diaryl-4-methoxy-2-pentanones by refluxing in methanol in the presence of hydrochloric acid. A detailed study of this general route is reported here.

  DOI：

  10.1021/jo960887a
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醚 、 aluminium amalgam 作用下， 生成 1-naphthylacetaldoxime
  参考文献：
  名称：

  Mayer,F.; Sieglitz, Chemische Berichte, 1922, vol. 55, p. 1854

  摘要：

  DOI：

文献信息

• One-pot enantioselective synthesis of (S)-spirobrassinin and non-natural (S)-methylspirobrassinin from amino acids using a turnip enzyme
  作者：Kaori Ryu、Seikou Nakamura、Souichi Nakashima、Hisashi Matsuda

  DOI：10.1007/s11418-020-01468-9

  日期：2021.3

  Abstract The enantioselective synthesis of (S)-(−)-spirobrassinin, which features a unique sulfur-containing spirooxindole skeleton, was achieved by focusing on the phytoalexin generation in Brassicaceae plants. Specifically, (S)-(−)-spirobrassinin was obtained in a one-pot fashion from l-tryptophan through a reaction involving S-spirocyclization with various turnip enzymes and constituents, i.e.,

  摘要 通过着重于十字花科植物中植物抗毒素的产生，实现了具有独特的含硫螺氧杂吲哚骨架的（S）-（-）-spirobrassinin的对映选择性合成。具体地，通过涉及与各种萝卜酶和成分的S-螺环化的反应，即使用萝卜作为反应试剂，催化剂和方法，以1-锅方式从1-色氨酸以单锅方式获得（S）-（-）-螺油菜素。反应容器。令人惊讶地，这种策略也使新的非天然spirooxindole（的一锅对映选择性合成小号） - （ - ） -从5-甲基-5- methylspirobrassinin DL色氨酸。 图形摘要
• Homologation of Aryl Aldehydes Using Nitromethane as a C1 Source Enabled by Nitrogen-Doped Carbon-Supported Palladium Catalysts
  作者：Tomohiro Yasukawa、Karin Sakamoto、Yasuhiro Yamashita、Shu̅ Kobayashi

  DOI：10.1021/acscatal.2c01008

  日期：——

  Homologation of aryl aldehydes provides useful synthetic intermediates, but it requires multistep reactions and generates significant amounts of waste. We considered such reactions using nitromethane as a C1 source through nitroolefin formation, partial hydrogenation to oximes, and hydration of oximes; however, the control of selectivity in the second reaction is challenging. To achieve this pathway

  芳基醛的同系化提供了有用的合成中间体，但它需要多步反应并产生大量废物。我们考虑了使用硝基甲烷作为 C1 源通过硝基烯烃形成、部分氢化成肟和肟水合的反应；然而，第二反应中选择性的控制具有挑战性。为了实现这一途径，开发了用于选择性氢化的氮掺杂碳嵌钯纳米颗粒催化剂。我们发现氮掺杂剂的存在有效地调整了催化活性，使其在环境压力下表现出几乎完美的选择性、高活性和可重复使用性。然后，我们在批处理和流动系统中进行了三步同源化反应，只需要一个纯化步骤。
• Synthesis, analysis and rearrangement of novel unnatural glucosinolates
  作者：Nicola E. Davidson、Trevor J. Rutherford、Nigel P. Botting

  DOI：10.1016/s0008-6215(00)00308-6

  日期：2001.2

  As part of a structure activity study to examine the interaction of glucosinolates with leaf surfaces,a number of glucosinolates were synthesised bearing novel side chain functionalities. These included 7-carboxyheptyl, heptyl, and naphthyl side chains. For the carboxyheptyl glucosinolate, a novel intramolecular rearrangement reaction was observed during the final deprotection step, which generated an ester attached to the C-3 of glucose. Studies by H-1 NMR spectroscopy showed that the hydrophobic side chain associated with one face of the glucose ring and it was proposed that this was the driving force for the rearrangement. Similar hydrophobic interactions were also observed between the heptyl and naphthyl side chains and the glucose. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Mayer,F.; Sieglitz, Chemische Berichte, 1922, vol. 55, p. 1854
  作者：Mayer,F.、Sieglitz

  DOI：——

  日期：——
• 3-Unsubstituted 1,5-Diaryl-2,4-pentanediones and -4-methoxy-2-pentanones:  Synthesis via Corresponding 3-Hydroxy Ketones Generated from 2-Isoxazolines
  作者：Juha T. Pulkkinen、Jouko J. Vepsäläinen

  DOI：10.1021/jo960887a

  日期：1996.1.1

  Aryl acetaldoximes are reacted with allylarenes in the presence of sodium hypochlorite to give 3,5-bis(arylmethyl)-2-isoxazolines which are then converted to 1,5-diaryl-4-hydroxy-2-pentanones by a reductive hydrogenation in the presence of water. These intermediate aldols can then be either oxidized with Corey-Kim reagent to stable dimethylsulfonium 1-(arylacetyl)-2-oxo-3-arylpropylides followed by zinc-acetic acid reduction to give 1,5-diaryl-2,4-pentanediones, or converted to 1,5-diaryl-4-methoxy-2-pentanones by refluxing in methanol in the presence of hydrochloric acid. A detailed study of this general route is reported here.