(S)-dimethyl 3,3'-(1-phenylethylazanediyl)dipropanoate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-dimethyl 3,3'-(1-phenylethylazanediyl)dipropanoate
• 英文别名: methyl 3-[(3-methoxy-3-oxopropyl)-[(1S)-1-phenylethyl]amino]propanoate
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: OYCCARZNJKOOHM-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-dimethyl 3,3'-(1-phenylethylazanediyl)dipropanoate 在 盐酸 、 水 、 sodium methylate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 9.0h， 生成 1-[(1S)-1-苯基乙基]-4-哌啶酮
  参考文献：
  名称：

  Synthesis and antihistamine evaluations of novel loratadine analogues

  摘要：

  A series of loratadine analogues containing hydroxyl group and chiral center were synthesized. The effect of the synthesized compounds on the histamine-induced contractions of guinea-pig ileum muscles was studied. In addition, the in vivo asthma-relieving effect of the analogues in the histamine induced asthmatic reaction in guinea-pigs was determined. Most of the compounds exhibited definite H-1 antihistamine activity. The S-enantiomers, compounds 2, 4 and 8, are more potent than the R-enantiomers, compounds 1, 3 and 7. Compound 6 was the most active one among the eight synthesized compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.012
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 丙烯酸甲酯（MA） 以 甲醇 为溶剂， 以85%的产率得到(S)-dimethyl 3,3'-(1-phenylethylazanediyl)dipropanoate
  参考文献：
  名称：

  Synthesis and structural characterization of zirconium complexes containing aminodiolate ligands and their use as Lewis acid catalysts

  摘要：

  一系列氨基二醇RN(CH2CH2C(OH)Rprime2)2（R，Rprime = Me，Me 4；Me，Ph 5；tert-butyl，Me 6；tert-Bu，Ph 7；（S）-PhCH(Me)，Me 8）通过将一级胺与丙烯酸甲酯进行Michael加成反应，然后将产生的氨基二酯与过量的甲基锂或苯基锂反应而制备。将氨基二醇4-8的两当量与四苄基锆反应，得到产率极高的锆双（氨基醇酸盐）10-14。在溶液和固态中，配合物11（R，Rprime = Me，Ph）采用顺式，fac-八面体几何构型。通过NMR光谱，配合物10-14在溶液中呈现流动性：氮原子上的小取代基和羟基碳上的大取代基降低了交换速率。手性配合物14在硝基醇（Henry）反应和以叔丁基过氧化氢氧化蒎草醇中作为Lewis酸催化剂，具有适度的对映选择性（分别为30%和46%对映体过量（ee））。关键词：二醇，Michael加成，锆，合成，结构，流动性，羟基醚，Lewis酸，催化。

  DOI：

  10.1139/v00-001

文献信息

• Synthesis and structural characterization of zirconium complexes containing aminodiolate ligands and their use as Lewis acid catalysts
  作者：Pengcheng Shao、Roland AL Gendron、David J Berg

  DOI：10.1139/v00-001

  日期：2000.2.6

  A series of aminodiols RN(CH₂CH₂C(OH)Rprime₂)₂ (R, Rprime = Me, Me 4; Me, Ph 5; tert-butyl, Me 6; tert-Bu, Ph 7; (S)-PhCH(Me), Me 8) were prepared by the Michael addition of a primary amine to methyl acrylate followed by reaction of the resulting aminodiester with excess methyl or phenyl lithium. Reaction of two equivalents of the aminodiols 4-8 with tetrabenzylzirconium afforded the zirconium bis(aminodiolates) 10-14 in excellent yield. Complex 11 (R, Rprime = Me, Ph) adopts a cis, fac-octahedral geometry in solution and in the solid state. Complexes 10-14 are fluxional in solution by NMR spectroscopy: small substituents at nitrogen and large substituents at the alkoxide carbons slow the rate of exchange. The chiral complex 14 functions as a Lewis acid catalyst in the nitroaldol (Henry) reaction and the oxidation of geraniol by tert-butyl hydroperoxide with modest enantioselectivities (30 and 46% enantiomeric excess (ee), respectively).Key words: diol, Michael addition, zirconium, synthesis, structure, fluxional, alkoxide, Lewis acid, catalysis.

  一系列氨基二醇RN(CH2CH2C(OH)Rprime2)2（R，Rprime = Me，Me 4；Me，Ph 5；tert-butyl，Me 6；tert-Bu，Ph 7；（S）-PhCH(Me)，Me 8）通过将一级胺与丙烯酸甲酯进行Michael加成反应，然后将产生的氨基二酯与过量的甲基锂或苯基锂反应而制备。将氨基二醇4-8的两当量与四苄基锆反应，得到产率极高的锆双（氨基醇酸盐）10-14。在溶液和固态中，配合物11（R，Rprime = Me，Ph）采用顺式，fac-八面体几何构型。通过NMR光谱，配合物10-14在溶液中呈现流动性：氮原子上的小取代基和羟基碳上的大取代基降低了交换速率。手性配合物14在硝基醇（Henry）反应和以叔丁基过氧化氢氧化蒎草醇中作为Lewis酸催化剂，具有适度的对映选择性（分别为30%和46%对映体过量（ee））。关键词：二醇，Michael加成，锆，合成，结构，流动性，羟基醚，Lewis酸，催化。
• Synthesis and antihistamine evaluations of novel loratadine analogues
  作者：Yue Wang、Juan Wang、Yan Lin、Li-Feng Si-Ma、Dong-hua Wang、Li-Gong Chen、Deng-Ke Liu

  DOI：10.1016/j.bmcl.2011.06.012

  日期：2011.8

  A series of loratadine analogues containing hydroxyl group and chiral center were synthesized. The effect of the synthesized compounds on the histamine-induced contractions of guinea-pig ileum muscles was studied. In addition, the in vivo asthma-relieving effect of the analogues in the histamine induced asthmatic reaction in guinea-pigs was determined. Most of the compounds exhibited definite H-1 antihistamine activity. The S-enantiomers, compounds 2, 4 and 8, are more potent than the R-enantiomers, compounds 1, 3 and 7. Compound 6 was the most active one among the eight synthesized compounds. (C) 2011 Elsevier Ltd. All rights reserved.