ethyl (2Z)-3-(4-chlorophenyl)-2-isothiocyanatoprop-2-enoate | 1026441-44-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (2Z)-3-(4-chlorophenyl)-2-isothiocyanatoprop-2-enoate
• 英文别名: ethyl (Z)-3-(4-chlorophenyl)-2-isothiocyanatoacrylate；ethyl (Z)-3-(4-chlorophenyl)-2-isothiocyanatoprop-2-enoate
• CAS: 1026441-44-0
• 化学式: C₁₂H₁₀ClNO₂S
• 分子量: 267.736
• InChiKey: CCIODMMBMLUDLV-XFFZJAGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-3-(4-chlorophenyl)-2-isothiocyanatoprop-2-enoate 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以1.07 g的产率得到2-thioxo-5-(4-chlorophenylmethylidene)-4-imidazolidinone
  参考文献：
  名称：

  The Synthesis of 2-Alkylthio-3-alkyl-5-arylmethylidene4H-imidazol-4-ones

  摘要：

  2-alkylthio-3-alkyl-5-arylmethylidene-4H-imidazol-4-ones were synthesized by the S-alkylation and N-alkylation of 2-thioxo-5-arylmethylidene-4-imidazolidinones, which were obtained via a tandem aza-Wittig reaction of vinyliminophosphoranes, carbon disulfide, and excess ammonium hydroxide (28% NH3 in water).

  DOI：

  10.1080/10426500600614147
• 作为产物：
  描述：

  ethyl (Z)-2-azido-3-(4-chlorophenyl)acrylate 以 二氯甲烷 为溶剂， 反应 34.0h， 生成 ethyl (2Z)-3-(4-chlorophenyl)-2-isothiocyanatoprop-2-enoate
  参考文献：
  名称：

  Synthesis of 5-arylidene-3-(pyridin-4-yl)-2-thio-imidazolidinone derivatives with the end of flexible chain modified with aryl groups under microwave

  摘要：

  DOI：

  10.1080/00397911.2022.2047727

文献信息

• Synthesis of (4<i>Z</i>)-4-(Arylmethylidene)-5-ethoxy-1,3-oxazolidine-2-thiones by the Reaction of Ethyl (2<i>Z</i>)-3-Aryl-2-isothiocyanatoprop-2-enoates with Organolithium Compounds
  作者：Kazuhiro Kobayashi、Kosuke Ezaki、Hiroo Hashimoto

  DOI：10.1002/hlca.201200479

  日期：2013.3

  A convenient one‐pot method for the preparation of (4Z)‐4‐(arylmethylidene)‐5‐ethoxy‐1,3‐oxazolidine‐2‐thiones 2 and 3 from ethyl (2Z)‐3‐aryl‐2‐isothiocyanatoprop‐2‐enoates 1, which can be easily prepared from ethyl 2‐azidoacetate and aromatic aldehydes, has been developed. Thus, these α‐isothiocyanato α,β‐unsaturated esters were treated with organolithium compounds, including lithium enolates of acetates

  一种方便的一锅法，可从乙基（2 Z）-3-芳基-2-基中制备（4 Z）-4-（芳基亚甲基）-5-乙氧基-1,3-恶唑烷-2-硫酮2和3已开发出可以轻松地由2-叠氮基乙酸乙酯和芳香族醛制备的异硫氰酸根合丙-2-烯酸酯1。因此，将这些α-异硫氰酸根合α，β-不饱和酯与有机锂化合物（包括乙酸烯醇锂）一起处理，以提供5-取代的（4 Z）-4-（芳基亚甲基）-5-乙氧基-1,3-恶唑烷- 2‐硫酮，2和2 ‐ [（4 Z）-（4-芳基亚甲基）-5-乙氧基-2-硫代-1,3-恶唑烷定-5-基]乙酸酯，3。
• New Facile Synthesis of Imidazo[2,1-<i>b</i>]-1,3,4-thiadiazol-5(6<i>H</i>)-ones via aza-Wittig Reaction
  作者：Ming-Wu Ding、Bo-Qiao Fu、Lin Cheng

  DOI：10.1055/s-2004-822333

  日期：——

  lidinones 4. Reactions of 4 with triphenyphosphine, hexachloroethane and Et 3 N produced iminophosphoranes 5. A tandem aza-Wittig reaction of iminophosphoranes 5 with isocyanates generated imidazo[2,1-b]-1,3,4-thiadiazol-5(6H)-ones 7 in moderate yield.

  异硫氰酸酯 2 由乙烯基亚氨基正膦 1 与 CS 2 的 aza-Wittig 反应获得，与肼反应生成 3-氨基-2-硫代-4-咪唑啉酮 4。 4 与三苯膦、六氯乙烷和 Et 3 N 反应生成亚氨基正膦 5。亚氨基正膦 5 与异氰酸酯的串联氮杂维蒂希反应以中等收率生成咪唑并[2,1-b]-1,3,4-噻二唑-5(6H)-ones 7。
• Facile synthesis of 2-alkylthio-3-amino-4H-imidazol-4-ones and 2H-imidazo[2,1-b]-1,3,4-thiadiazin-6(7H)-ones viaN-vinylic iminophosphorane
  作者：Ming-Wu Ding、Bo-Qiao Fu、Ju-Zhen Yuan

  DOI：10.1002/hc.20069

  日期：——

  by S-alkylation of 2-thioxo-3-amino-4-imidazolidinones 4, which were obtained via cyclization of isothiocyanates 2 with hydrazine hydrate. 5l–n reacted with Ph3P, C2Cl6, and NEt3 to give 2H-imidazo[2,1-b]-1,3,4-thiadiazin- 6(7H)-ones 7a–c in good yields. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:76–80, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc

  2-Alkylthio-3-amino-4H-imidazol-4-ones 5 通过 2-thioxo-3-amino-4-imidazolidinones 4 的 S-烷基化合成，2-thioxo-3-amino-4-imidazolidinones 4 是通过异硫氰酸酯 2 与水合肼环化获得的。5l–n 与 Ph3P、C2Cl6 和 NEt3 反应生成 2H-咪唑并[2,1-b]-1,3,4-噻二嗪-6(7H)-ones 7a-c，收率良好。© 2005 Wiley Periodicals, Inc. 杂原子化学 16:76–80, 2005; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20069
• The Synthesis of 2-Alkylthio-3-alkyl-5-arylmethylidene4<i>H</i>-imidazol-4-ones
  作者：Yong Sun、Li-Ping Gao、Zhi-Qiang Guo、Ming-Wu Ding

  DOI：10.1080/10426500600614147

  日期：2006.9.1

  2-alkylthio-3-alkyl-5-arylmethylidene-4H-imidazol-4-ones were synthesized by the S-alkylation and N-alkylation of 2-thioxo-5-arylmethylidene-4-imidazolidinones, which were obtained via a tandem aza-Wittig reaction of vinyliminophosphoranes, carbon disulfide, and excess ammonium hydroxide (28% NH3 in water).
• Synthesis of 5-arylidene-3-(pyridin-4-yl)-2-thio-imidazolidinone derivatives with the end of flexible chain modified with aryl groups under microwave
  作者：Chongyang Mao、Zhen Cao、Boqiao Fu、Shengcheng Wang、Haowei Chen、Caifen Xia、Xinliang Hu、Xinyuan Huang、Caiqin Qin

  DOI：10.1080/00397911.2022.2047727

  日期：2022.3.4