β-(phenylseleno)acrylic acid | 15905-30-3

• 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: β-(phenylseleno)acrylic acid
• 英文别名: (2Z)-3-(phenylselanyl)acrylic acid；(Z)-3-(phenylseleno)acrylic acid；3-(phenylselanyl)acrylic acid；3c-phenylselanyl-acrylic acid；3c-Phenylselanyl-acrylsaeure；cis-3-Phenylseleno-acrylsaeure；(Z)-3-phenylselanylprop-2-enoic acid
• CAS: 15905-30-3
• 化学式: C₉H₈O₂Se
• 分子量: 227.121
• InChiKey: NSIXWDHGRWRYKE-SREVYHEPSA-N

物化性质

• 熔点：
  125-126.5 °C
• 沸点：
  338.0±34.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.61
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  β-(phenylseleno)acrylic acid 在 溴 、 溶剂黄146 作用下， 生成 (E)-2-(phenylseleno)-1-bromoethylene
  参考文献：
  名称：

  Chierici; Montanari, Gazzetta Chimica Italiana, 1956, vol. 86, p. 1269,1276

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯基二硒醚 、 丙炔酸乙酯 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以65%的产率得到β-(phenylseleno)acrylic acid
  参考文献：
  名称：

  Platinum-Catalyzed Intramolecular Vinylchalcogenation of Alkynes with β-Phenylchalcogeno Conjugated Amides

  摘要：

  Platinum-catalyzed intramolecular vinylthiolation and -selenation of internal alkynes with vinylchalcogenides 1 having a carbamoyl group on cis-beta-position of vinyl moiety was developed. The conjugated six-membered lactam framework 2 was constructed in 1 high yields. Density functional theory calculations for alkyne insertion processes suggest seven-membered platinacycle 3 is a kinetically favored intermediate of this catalytic system.

  DOI：

  10.1021/ja804121j

文献信息

• Organylzinc Chalcogenolate Promoted Michael-Type Addition of α,β-Unsaturated Carbonyl Compounds
  作者：Vanessa Lóren Nunes、Ingryd Cristina de Oliveira、Olga Soares do Rêgo Barros

  DOI：10.1002/ejoc.201301497

  日期：2014.3

  chalcogenide compounds promoted by organylzinc chalcogenolates. In this protocol, reductive cleavage of diorganyl dichalcogenide bonds by the Zn/NH4OH system led to organylzinc chalcogenolates. The reaction was performed with propiolic acids and esters and afforded β-organochalcogenacrylic acids and esters under mild basic conditions. The stereochemistry corresponded to anti-Markovnikov addition of the organyl

  我们介绍了有机基锌硫属元素化物促进的乙烯基硫属元素化物化合物的化学、区域和立体选择性合成。在该协议中，Zn/NH4OH 系统对二有机二硫属化物键的还原裂解导致有机锌硫属元素酸盐。该反应用丙炔酸和酯进行，在温和的碱性条件下得到 β-有机硫代丙烯酸和酯。立体化学对应于跨三键的有机硫族化合物成分的反马尔科夫尼科夫加成。
• Tsoi, L. A.; Patsaev, A. K.; Ushanov, V. Zh., Journal of Organic Chemistry USSR (English Translation), 1984, p. 1897 - 1902
  作者：Tsoi, L. A.、Patsaev, A. K.、Ushanov, V. Zh.、Vyaznikovtsev, L. V.

  DOI：——

  日期：——
• TSOJ, L. A.;PATSAEV, A. K.;USHANOV, V. ZH.;VYAZNIKOVTSEV, L. V., ZH. ORGAN. XIMII, 1984, 20, N 10, 2081-2086
  作者：TSOJ, L. A.、PATSAEV, A. K.、USHANOV, V. ZH.、VYAZNIKOVTSEV, L. V.

  DOI：——

  日期：——
• Chierici; Montanari, Gazzetta Chimica Italiana, 1956, vol. 86, p. 1269,1276
  作者：Chierici、Montanari

  DOI：——

  日期：——
• Platinum-Catalyzed Intramolecular Vinylchalcogenation of Alkynes with β-Phenylchalcogeno Conjugated Amides
  作者：Masashi Toyofuku、Shin-ichi Fujiwara、Tsutomu Shin-ike、Hitoshi Kuniyasu、Nobuaki Kambe

  DOI：10.1021/ja804121j

  日期：2008.8.13

  Platinum-catalyzed intramolecular vinylthiolation and -selenation of internal alkynes with vinylchalcogenides 1 having a carbamoyl group on cis-beta-position of vinyl moiety was developed. The conjugated six-membered lactam framework 2 was constructed in 1 high yields. Density functional theory calculations for alkyne insertion processes suggest seven-membered platinacycle 3 is a kinetically favored intermediate of this catalytic system.