ethyl 2-acetyl-2-fluoro-4-nitro-3-phenylbutanoate | 1157864-76-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-acetyl-2-fluoro-4-nitro-3-phenylbutanoate
• CAS: 1157864-76-0
• 化学式: C₁₄H₁₆FNO₅
• 分子量: 297.283
• InChiKey: JWBFPNFXORHVET-UHFFFAOYSA-N

物化性质

• 沸点：
  423.3±45.0 °C(predicted)
• 密度：
  1.233±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氟乙酰乙酸乙酯 、 β-硝基苯乙烯 在 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea 作用下， 以 甲基叔丁基醚 为溶剂， 反应 8.0h， 以28%的产率得到
  参考文献：
  名称：

  New class of bifunctional thioureas from l-proline: highly enantioselective Michael addition of 1,3-dicarbonyls to nitroolefins

  摘要：

  A new class of bifunctional tertiary amine thiourea was synthesized from L-proline. The reported thiourea is amenable to steric and electronic modifications at the stereogenic center bearing a thiourea moiety. Excellent enantioselectivity was obtained in the Michael addition of 2,4-pentanedione to various nitro olefins using the new organocatalyst. The construction of contiguous stereocenters via the Michael reaction of substituted 1,3-dicarbonyls to nitro olefins was also carried out with very good yield, enantioselectivity, and diastereoselectivity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.02.011

文献信息

• Asymmetric generation of fluorine-containing quaternary carbons adjacent to tertiary stereocenters: uses of fluorinated methines as nucleophiles
  作者：Xiao Han、Jie Luo、Chen Liu、Yixin Lu

  DOI：10.1039/b823184b

  日期：——

  Organocatalytic asymmetric Michael reactions of fluorinated nucleophiles with nitroolefins catalyzed by Cinchona alkaloid-derived thiourea catalysts generated the desired Michael products containing vicinal fluorinated quaternary and tertiary chiral centers with exceptional enantioselectivity.

  由金鸡纳生物碱衍生的硫脲催化剂催化的氟化亲核试剂与硝基烯烃的有机催化不对称迈克尔反应生成了所需的迈克尔产物，该产物含有邻位氟化的季铵和叔手性中心，并具有出色的对映选择性。
• β-Isocupreidinate‒CaAl-layered double hydroxide composites—heterogenized catalysts for asymmetric Michael addition
  作者：Gábor Varga、Viktória Kozma、Vanessza Judit Kolcsár、Ákos Kukovecz、Zoltán Kónya、Pál Sipos、István Pálinkó、György Szὅllὅsi

  DOI：10.1016/j.mcat.2019.110675

  日期：2020.2

  beta-isocupreidinate (beta-iCu) anions having well-known structure and catalytic activity in various asymmetric reactions, were incorporated into the interlayer gallery of hydrocalumite (CaAl-LDH) by the partial delamination-restacking method. Silylation of the outer surface of the LDH with trimethyl silane was also employed to avoid the adsorption of beta-iCu on the outer surface and to block the basic sites there. The obtained materials were characterized by a range of instrumental methods (X-ray diffractometry, scanning electron microscopy, ATR-IR and grazing incidence IR spectroscopies). The catalytic activities of the composites were tested in the asymmetric Michael addition of beta-nitrostyrene and ethyl 2-fluoroacetoacetate. The beta-iCu-pillared LDHs proved to be active and recyclable catalysts with very good diastereoselectivities and acceptable and in 2-propanol very good enantioselectivities. The silylated composite retained its activity and diastereoselectivity even in the third repeated run, when heptane was the solvent.