(4R,5R)-4-N,4-N,5-N,5-N-tetramethyl-2-phenyl-1,3-dioxolane-4,5-dicarboxamide | 141376-11-6

• 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: (4R,5R)-4-N,4-N,5-N,5-N-tetramethyl-2-phenyl-1,3-dioxolane-4,5-dicarboxamide
• CAS: 141376-11-6
• 化学式: C₁₅H₂₀N₂O₄
• 分子量: 292.335
• InChiKey: PBEXFSRBVFTWLJ-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.65
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  59.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-N,4-N,5-N,5-N-tetramethyl-2-phenyl-1,3-dioxolane-4,5-dicarboxamide 在 红铝 作用下， 生成 (4S,5S)-2-phenyl-4,5-bis((N,N-dimethylamino)methyl)-1,3-dioxolane
  参考文献：
  名称：

  Tartrate-derived aryl aldehyde acetals in the asymmetric directed metalation of chromium tricarbonyl arene complexes

  摘要：

  A series of three chromium tricarbonyl benzaldehyde acetal complexes were prepared from benzaldehyde diethyl acetal and (+)-diethyl tartrate. These compounds were ortho-lithiated by a number of bases, and the diastereoselectivity of lithiation was determined by quenching of the resulting anions with Me3SiCl. Complexes 1 and 2 were found to give moderate levels of diastereoselection, while the combination of complex 3 and 2.4 equiv of n-BuLi under equilibrating conditions gave an 86% de of silylated products. Other electrophiles gave slightly higher de's (88% to greater-than-or-equal-to 94%), and all products derived from 3 were separable by column chromatography. Hydrolysis of the ortho-methylated product to the corresponding benzaldehyde complex (-)-21 as well as X-ray structural analysis of the trimethylsilylated complex demonstrated that preferential pro-R deprotonation had occurred.

  DOI：

  10.1021/jo00075a008
• 作为产物：
  描述：

  N,N,N’,N’-四甲基-L-酒石酰胺 、 苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以69%的产率得到(4R,5R)-4-N,4-N,5-N,5-N-tetramethyl-2-phenyl-1,3-dioxolane-4,5-dicarboxamide
  参考文献：
  名称：

  Asymmetric deprotonation and complexation reactions mediated by chiral ketals as a route to ortho-disubstituted (.eta.6-arene)Cr(CO)3 complexes

  摘要：

  A series of chiral ketals derived from an aryl ketone or aldehyde and one of several C2-symmetrical diols were converted to their corresponding (eta-6-arene)Cr(CO)s complexes. The resultant 1,3-dioxolanes were trans substituted at C-4 and C-5 by groups CH2X, where X = H (1), OCH3 (2), or N(CH3)2 (3). Ortho deprotonation was attempted on complexes 1-3 using tert-butyllithium in THF solution to afford the corresponding lithio derivatives, which were treated with a variety of electrophiles (MeOSO2F, TMSCl, Ph2C(O), Ph2PCl). Although 1 gave a complex mixture of products, complexes 2 and 3 afforded good yields of disubstituted complexes (with the exception that the lithiated derivative of 3 did not undergo methylation when treated with MeOSO2F). The stereoselectivity of the reactions was determined by NMR spectroscopy and found to be in the range of 3:1 for 2 and >9.1 for 3. The sense of diastereoselection were identified by chemical correlations (for compounds derived from 2) and by circular dichroism spectroscopy. Poor diastereoselection was obtained when this protocol was performed on the corresponding acetal ultimately derived from benzaldehyde and N,N,N',N-tetramethyl-1,4-diamino-2,3-butanediol. In addition, a related series of ortho-disubstituted arenes bearing chiral ketal or acetal substituents in the benzylic position were subjected to complexation reactions with (naphthalene)Cr(CO)3 in dibutyl ether. The best diastereoselectivity observed with this methodology was 48%, obtained with the acetal derived from o-tolualdehyde and N,N,N',N-tetramethyltartramide.

  DOI：

  10.1021/jo00039a012

文献信息

• Enantiopure Quaternary α-Trifluoromethyl-α-alkoxyaldehydes from <scp>l</scp>-Tartaric Acid Derived Ketoamides
  作者：Jean Nonnenmacher、Fabien Massicot、Fabienne Grellepois、Charles Portella

  DOI：10.1021/jo8013403

  日期：2008.10.17

  The diastereoselective nucleophilic trifluoromethylation of a range of ketoamides derived from L-tartaric acid has been studied. TMSCF3 in the presence of a catalytic amount of K2CO3 in DMF has been identified as the conditions leading to the highest diastereoselectivities. A sequential one-pot reaction trifluoromethylation-etherification of the trifluoromethylcarbinol has been developed. Only one

  已经研究了衍生自L-酒石酸的一系列酮酰胺的非对映选择性亲核三氟甲基化。TMSCF3在DMF中催化量的K2CO3的存在下被确定为导致最高非对映选择性的条件。已经开发出三氟甲基甲醇的顺序一锅反应三氟甲基化-醚化。缩酮水解-氧化裂解仅是另外的一锅法反应，导致最终的α-三氟甲基化的α-烷氧基醛。该方法用于制备一系列对映体纯的芳基，杂芳基和烷基α-三氟甲基-α-烷氧基醛。