1,2,3-trimethoxy-5-(2-nitrobut-1-enyl)benzene | 134538-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2,3-trimethoxy-5-(2-nitrobut-1-enyl)benzene
• 英文别名: 1,2,3-trimethoxy-5-[(E)-2-nitrobut-1-enyl]benzene
• CAS: 134538-53-7
• 化学式: C₁₃H₁₇NO₅
• 分子量: 267.282
• InChiKey: UWENFVIORVCKFM-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2,3-trimethoxy-5-(2-nitrobut-1-enyl)benzene 、 (1R,7R)-9,9-dimethyl-4-hydrido-4-oxo-2,2,6,6-tetraphenyl-3,5,8,10-tetraoxa-4-phosphabicyclo[5.3.0]decane 在 四甲基乙二胺 、 diethylzinc 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 12.0h， 生成 (3aR,8aR)-2,2-dimethyl-6-[2-nitro-1-(3,4,5-trimethoxyphenyl)butyl]-4,4,8,8-tetraphenylperhydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one 、 (3aR,8aR)-2,2-dimethyl-6-[2-nitro-1-(3,4,5-trimethoxyphenyl)butyl]-4,4,8,8-tetraphenylperhydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepin-6-one
  参考文献：
  名称：

  手性亚磷酸酯对硝基烯烃和 Knoevenagel 受体的不对称迈克尔加成

  摘要：

  描述了对映体纯亚磷酸酯与硝基烯烃和 α,β-不饱和丙二酸酯的非对映选择性迈克尔加成。使用现成的 TADDOL 辅助剂获得了高度不对称的感应。助剂的无外消旋裂解分别导致 α-取代的 β-硝基膦酸盐和 β-取代的 β-膦酰基丙二酸盐分别以良好的收率和高对映体过量。还报道了将该方法扩展到合成具有两个新的相邻立体中心的 α,β-二取代 β-硝基膦酸盐。

  DOI：

  10.1055/s-2006-926437
• 作为产物：
  描述：

  1-(3,4,5-trimethoxyphenyl)-2-butanone 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 乙二醇二甲醚 为溶剂， 反应 10.17h， 生成 1,2,3-trimethoxy-5-(2-nitrobut-1-enyl)benzene
  参考文献：
  名称：

  Palladium-catalyzed synthesis of substituted nitroolefins

  摘要：

  A one-pot protocol toward several substituted nitroolefins 4 and 6 starting with substituted acetones 2 and 5 was described. A facile process was carried out for the triflation of substituted acetones 2 and 5 with triflic anhydride (Tf2O) under the basic condition (Cs2CO3) and then palladium-catalyzed cross-coupling of enol triflates 3 with NaNO2 and BINAP in the presence of phase-transfer reagents (n-Bu4NBr) under the refluxing 1,2-dimethoxyethane (DME) in acceptable yields. (C) 2013 Elsevier Ltd. All rights reserved,

  DOI：

  10.1016/j.tetlet.2013.04.038

文献信息

• Henry condensation under high pressure 2. Effect of aromatic aldehyde type and pressure on the yield of ?-nitrostyrenes and secondary processes
  作者：N. E. Agafonov、I. P. Sedishev、A. V. Dudin、A. A. Kutin、G. A. Stashina、V. M. Zhulin

  DOI：10.1007/bf00965433

  日期：1991.2

  Condensation of aromatic aldehydes (I)-(XX) with EtNO2 and n-PrNO2 in AcOH in the presence of AcONH4 or i-BuNH2 gives primarily omega-nitrostyrenes (Ia, b)-(XXa, b) and small quantities of nitriles (Ic)-(XXc), oximes (Id)-(XXd), and ketones (Ie, f)-(XXe, f). The yields of (Ia, b)-(XXa, b) at P = 1 atm are higher for acceptor substituents on the aromatic ring whereas at P = 10 kbar, they are higher for donor substituents. High pressures suppress the formation of (Ic-f)-(XXc-f) and the Z-isomers of (Ia, b)-(XXa, b). The high pressure technique is especially useful in the preparation of donor-substituted (Ia, b)-(XXa, b) which are intermediates in the synthesis of the psychotropic beta-phenylethylamines.
• AGAFONOV, I. E.;SEDISHEV, I. I.;DUDIN, A. V.;KUTIN, A. A.;STASHINA, G. A.+, IZV. AN CCCP. CEP. XIM.,(1991) N, S. 426-433
  作者：AGAFONOV, I. E.、SEDISHEV, I. I.、DUDIN, A. V.、KUTIN, A. A.、STASHINA, G. A.+

  DOI：——

  日期：——
• Palladium-catalyzed synthesis of substituted nitroolefins
  作者：Meng-Yang Chang、Chung-Han Lin、Hang-Yi Tai

  DOI：10.1016/j.tetlet.2013.04.038

  日期：2013.6

  A one-pot protocol toward several substituted nitroolefins 4 and 6 starting with substituted acetones 2 and 5 was described. A facile process was carried out for the triflation of substituted acetones 2 and 5 with triflic anhydride (Tf2O) under the basic condition (Cs2CO3) and then palladium-catalyzed cross-coupling of enol triflates 3 with NaNO2 and BINAP in the presence of phase-transfer reagents (n-Bu4NBr) under the refluxing 1,2-dimethoxyethane (DME) in acceptable yields. (C) 2013 Elsevier Ltd. All rights reserved,
• Asymmetric Michael Additions of a Chiral Phosphite to Nitroalkenes and Knoevenagel Acceptors
  作者：Dieter Enders、Livio Tedeschi、Dominik Förster

  DOI：10.1055/s-2006-926437

  日期：2006.5

  The diastereoselective Michael addition of an enantiopure phosphite to nitroalkenes and α,β-unsaturated malonates is described. High asymmetric inductions were obtained using a readily available TADDOL auxiliary. Racemization-free cleavage of the auxiliary led to α-substituted β-nitro phosphonates and β-substituted β-phosphono malonates in good yields and high enantiomeric excesses, respectively. An

  描述了对映体纯亚磷酸酯与硝基烯烃和 α,β-不饱和丙二酸酯的非对映选择性迈克尔加成。使用现成的 TADDOL 辅助剂获得了高度不对称的感应。助剂的无外消旋裂解分别导致 α-取代的 β-硝基膦酸盐和 β-取代的 β-膦酰基丙二酸盐分别以良好的收率和高对映体过量。还报道了将该方法扩展到合成具有两个新的相邻立体中心的 α,β-二取代 β-硝基膦酸盐。