((E)-3-isothiocyanatoprop-1-enyl)benzene | 474055-66-8

• 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: ((E)-3-isothiocyanatoprop-1-enyl)benzene
• 英文别名: (E)-(3-isothiocyanatopropenyl)benzene；trans-cinnamyl isothiocyanate；trans-Cinnamylisothiocyanat；cinnamylisothiocyanate；Cinnamyl isothiocyanate；[(E)-3-isothiocyanatoprop-1-enyl]benzene
• CAS: 474055-66-8
• 化学式: C₁₀H₉NS
• 分子量: 175.254
• InChiKey: JHZPNZCRVCOUIA-QPJJXVBHSA-N

物化性质

• 沸点：
  316.2±21.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ((E)-3-isothiocyanatoprop-1-enyl)benzene 、 phenylmagnesium bromide 生成 N-cinnamylbenzothioamide
  参考文献：
  名称：

  The Cyclization of N-Alkenylthionamides to Thiazolines and Dihydrothiazines

  摘要：

  DOI：

  10.1021/jo01063a038
• 作为产物：
  描述：

  (E)-(3-isocyanoprop-1-en-1-yl)benzene 在 Mo(O)(S₂CNEt₂)2 sulfur 作用下， 以 丙酮 为溶剂， 反应 72.0h， 以68%的产率得到((E)-3-isothiocyanatoprop-1-enyl)benzene
  参考文献：
  名称：

  Direct Synthesis of Isothiocyanates from Isonitriles by Molybdenum-Catalyzed Sulfur Transfer with Elemental Sulfur

  摘要：

  The direct molybdenum-catalyzed sulfuration of a variety of isonitriles with elemental sulfur or propene sulfide as sulfur donors affords the corresponding isothiocyanates in good yields and under mild reaction conditions. A catalytic cycle is suggested, in which the molybdenum oxo disulfur complex operates as the active sulfur-transferring species. A novel adduct between the isonitrile and the molybdenum complex has been characterized by X-ray analysis and its association constant determined by UV-vis spectroscopy, but this adduct appears not to be involved in the sulfur-transfer process.

  DOI：

  10.1021/jo026042i

文献信息

• Substituted isoxazolines for control of plant phytopathogens
  申请人：Eli Lilly and Company

  公开号：US04283403A1

  公开（公告）日：1981-08-11

  A class of 2-isoxazolines bearing an aryl substituent at the 3-position and a substituted methyl or ethyl group at the 5-position effectively control microorganisms, particularly fungal foliar phytopathogens.

  一类在3位带有芳基取代基、在5位带有取代甲基或乙基取代基的2-异噁唑啉类化合物能有效控制微生物，特别是真菌性叶部植物病原体。
• Synthesis of Isothiocyanates by Reaction of Amides with Carbon Disulfide in the Presence of Solid Potassium Carbonate/Sodium Hydroxide Mixture
  作者：Domenico Albanese、Michele Penso

  DOI：10.1055/s-1991-26629

  日期：——

  Readily available N-monosubstituted trifluoroacetamides are transformed into isothiocyanates in good yield by reaction, at room temperature, with carbon disulfide in acetonitrile in the presence of anhydrous sodium hydroxide/potassium carbonate basic mixture.

  可 readily获得的N-单取代三氟乙酰胺在室温下与碳二硫化物在乙腈中反应，在无水氢氧化钠/碳酸钾的碱性混合物存在下，良好产率转化为异硫氰酸酯。
• Efficient Synthesis of Isothiocyanates Based on the Tandem Staudinger/aza-Wittig Reactions and Mechanistic Consideration of the Tandem Reactions
  作者：Takeshi Isoda、Kazuhiko Hayashi、Satoshi Tamai、Toshio Kumagai、Yoshimitsu Nagao

  DOI：10.1248/cpb.54.1616

  日期：——

  The tandem and stepwise Staudinger/aza-Wittig reactions of several azides were examined in detail. The tandem reaction method (Method I) exhibited superior results in the yield of the corresponding isothiocyanates bearing an electron-withdrawing group than the conventional stepwise method (Method II) which involves the sequential treatment of the azides with triphenylphosphine and then carbondisulfide

  详细检查了几种叠氮化物的串联和逐步施陶丁格/氮杂-维蒂希反应。串联反应方法（方法Ⅰ）在具有带吸电子基团的相应异硫氰酸酯的收率方面优于常规的逐步方法（方法Ⅱ），后者涉及先用三苯膦再用二硫化碳对叠氮化物进行处理。在1 H-NMR分析的基础上，提出了两种反应方法的机理考虑。
• Thiocyanation of Allylic Alcohols Promoted by Trifluoroacetic Acid
  作者：Wen Xia、Liangzhen Hu、Chenglong Ma、Jiaqi Cao、Xiaohui Zhang、Yan Xiong

  DOI：10.1002/ejoc.202300148

  日期：——

  A rapid and efficient, acid-promoted strategy to access allylic thiocyanates using allylic alcohols as substrates and easily-available NH4SCN as the thiocyanate source is presented under metal- and oxidant-free conditions. Various tertiary and secondary allylic alcohols are tolerated in this mild reaction system.

  在无金属和氧化剂的条件下，使用烯丙醇作为底物和易于获得的 NH 4 SCN 作为硫氰酸盐源，提出了一种快速有效的酸促进策略来获得烯丙基硫氰酸盐。在这个温和的反应体系中可以容忍各种叔和仲烯丙醇。
• Iliceto,A.; Gaggia,G., Gazzetta Chimica Italiana, 1960, vol. 90, p. 262 - 268
  作者：Iliceto,A.、Gaggia,G.

  DOI：——

  日期：——