S-cis-Z-3-(2-naphthyl)-3-chloro-2-propenal | 4302-37-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: S-cis-Z-3-(2-naphthyl)-3-chloro-2-propenal
• 英文别名: Z-3-(2-naphthyl)-3-chloro-2-propen-1-al；(Z)-3-chloro-3-(2-naphthyl)-2-propenal；(Z)-3-chloro-3-(2-naphthyl)prop-2-enal；(Z)-3-(2-naphthyl)-3-chloropropenal；(Z)-3-chloro-3-(2-naphthyl)propenal；β-Chlor-β-(β-naphthyl)-acrolein；z-3-(2-Naphthyl)-3-chloro-2-propenal；(Z)-3-chloro-3-naphthalen-2-ylprop-2-enal
• CAS: 4302-37-8
• 化学式: C₁₃H₉ClO
• 分子量: 216.667
• InChiKey: YIDWVVQAFUYLQL-QPEQYQDCSA-N

物化性质

• 沸点：
  376.9±21.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  S-cis-Z-3-(2-naphthyl)-3-chloro-2-propenal 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以74%的产率得到5-(2-naphthyl)pyrazole
  参考文献：
  名称：

  Synthesis of some naphthyl-substituted nitrogen heterocycles on the basis of (Z)-3-chloro-3-(2-naphthyl)propenal

  摘要：

  (Z)-3-氯-3-(2-萘基)丙烯醛分别与肼、邻苯二胺、羟胺和甲酰胺反应，合成了吡唑、苯并二氮杂卓、异噁唑和嘧啶的β-萘基取代衍生物。

  DOI：

  10.1007/s11178-005-0050-0
• 作为产物：
  描述：

  2-萘乙酮 在 五氯化磷 作用下， 以 水 为溶剂， 生成 S-cis-Z-3-(2-naphthyl)-3-chloro-2-propenal
  参考文献：
  名称：

  Synthesis of 2-(2-Naphthyl)quinolines from Z-3-(2-Naphthyl)-3-chloro-2-propenal

  摘要：

  By reaction of Z-3-(2-naphthyl)-3-chloro-2-propenal and aromatic amines 1-(2-naphthyl)-3-iminoaryl-1-propenylarylamines were prepared which at heating in the glacial acetic acid afforded the corresponding 2-(2-naphthyl)quinolines.

  DOI：

  10.1023/b:rujo.0000013132.91639.76

文献信息

• Base-Promoted Intermolecular Cyclization of Substituted 3-Aryl(Heteroaryl)-3-chloroacrylaldehydes and Tetrahydroisoquinolines: An Approach to Access Pyrrolo[2,1-<i>a</i>]isoquinolines
  作者：Ziqi Yang、Ning Lu、Zhonglin Wei、Jungang Cao、Dapeng Liang、Haifeng Duan、Yingjie Lin

  DOI：10.1021/acs.joc.6b01781

  日期：2016.12.2

  We have developed a new base-promoted intermolecular cascade cyclization reaction of substituted 3-aryl(heteroaryl)-3-chloroacrylaldehydes and tetrahydroisoquinolines in one pot. The reaction provides a facile and practical synthesis of pyrrolo[2,1-a]isoquinolines. A number of pyrrolo[2,1-a]isoquinolines were synthesized in moderate to high yields (up to 97%).

  我们已经开发了一种新的碱促进的在一锅中取代的3-芳基（杂芳基）-3-氯丙烯醛和四氢异喹啉的分子间级联环化反应。该反应提供了吡咯并[2，1- a ]异喹啉的简便实用的合成方法。合成了许多吡咯并[2,1- a ]异喹啉，中度至高产率（高达97％）。
• Stereoselective One-Pot Sequential Dehydrochlorination/<i>trans</i> -Hydrofluorination Reaction of β-Chloro-α,β-unsaturated Aldehydes or Ketones: Facile Access to (<i>Z</i> )-β-Fluoro-β-arylenals/β-Fluoro-β-arylenones
  作者：Jingli Zhang、Liran Liu、Junxin Duan、Lianghu Gu、Bifeng Chen、Taolei Sun、Yuefa Gong

  DOI：10.1002/adsc.201700981

  日期：2017.12.19

  high potential as a fluorinated synthon in organic synthesis. However, control of the Z/E stereoselectivity of multi‐substituted monofluoroalkene products in one‐pot reactions still remains a challenge. An unprecedented one‐pot approach for the highly regio‐ and stereoselective preparation of functionalized (Z)‐β‐monofluoro tri‐substituted alkenes from readily available β‐chloro‐α,β‐unsaturated aldehydes

  一氟烯烃亚结构作为有机合成中的氟化合成子显示出很高的潜力。然而，在一锅反应中控制多取代一氟烯烃产物的Z / E立体选择性仍然是一个挑战。对于从容易获得的β-氯代-α，β-不饱和醛或酮进行高度区域和立体选择性制备官能化（Z）-β-单氟三取代烯烃的空前单锅方法已被探索。机理研究表明，该反应是通过将底物脱氯化氢而生成炔基醛/酮，然后将其反式引发的。-氟化氢。值得一提的是，具有适当碱性和亲核性的氟化剂在促进（Z）-β-氟-β-芳基三取代单氟烯烃的形成中起着关键作用。
• Synthesis of azirines containing aldehyde functionality and their utilization as synthetic tools for five membered oxazoles and isoxazoles
  作者：Sulagna Brahma、Jayanta K. Ray

  DOI：10.1002/jhet.5570450203

  日期：2008.3

  A simple and useful procedure for the synthesis of azirines containing aldehyde functionality from open chain bromo/chloro-aldehydes at room temperature is reported. The scope of the ring expansion reaction of a number of 3-substituted-2-formyl-azirines has been examined using different oraganometallic catalysts and a variety of Lewis acids.

  报道了一种在室温下由开链溴/氯醛合成含醛官能团的叠氮基的简单有用的方法。已经使用不同的有机金属催化剂和多种路易斯酸检查了许多3-取代的2-甲酰基-叠氮基的扩环反应的范围。
• Uncommon Heterocyclization into a Pyrazole System of Z-3-(2-Naphthyl)-3-chloro-2-propenal Semicarbazone and Thiosemicarbazone
  作者：E. V. Vashkevich、V. I. Potkin、N. G. Kozlov

  DOI：10.1007/s11178-005-0235-6

  日期：2005.5

  By reaction of Z-3-(2-naphthyl)-3-chloro-2-propenal with semicarbazide hydrochloride and thiosemicarbazide the corresponding semicarbazone and thiosemicarbazone were obtained that underwent a heterocyclization into a pyrazole system with elimination of amide moieties and with migration of the naphthyl fragment into the position 4 of the pyrazole ring. The alkylation of 4-(2-naphthyl)pyrazole synthesized with 2-nitropentachloro-1,3-butadiene afforded 1,1-bis[4-(2-naphthyl)-pyrazol-1-yl]-2-nitrotrichloro-1,3-butadiene.

  Z-3-(2-萘基)-3-氯-2-丙烯醛与盐酸氨基脲和氨基硫脲反应，得到相应的氨基脲和氨基硫脲，它们经过杂环化形成吡唑体系，消除酰胺部分并迁移萘基片段进入吡唑环的4位。用2-硝基五氯-1,3-丁二烯合成4-(2-萘基)吡唑烷基化得到1,1-双[4-(2-萘基)-吡唑-1-基]-2-硝基三氯-1， 3-丁二烯。
• Synthesis and Properties of Copper, Mercury, and Silver (2-Naphthyl)acetylenides
  作者：E. A. Dikusar、V. I. Potkin、E. V. Vashkevich、N. G. Kozlov、R. V. Kaberdin

  DOI：10.1023/b:rugc.0000031860.91216.62

  日期：2004.4

  (Z)-2-Naphthylacetylene was synthesized by the reaction of (Z)-3-(2-naphthyl)-3-chloropropenal (prepared from 2-acetylnaphthalene) with aqueous NaOH in dioxane. The reactions of 2-naphthylacetylene with CuCl, [Ag(NH3)(2)]NO3, and K-2[HgI4] gave copper, silver, and mercury 2-naphthylacetylenides, respectively. Silver naphthylacetylenide reacts with iodine to give the iodoethynyl derivative, which readily takes up bromine across the triple bond.