(4R,5R)-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4,5-bis(N-benzylamide) | 189574-20-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4,5-bis(N-benzylamide)
• 英文别名: N,N'-dibenzyl(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxamide；(4R,5R)-N(4),N(5)-dibenzyl-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxamide；(4R,5R)-N,N'-dibenzyl-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxamide；(4R,5R)-4-N,5-N-dibenzyl-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxamide
• CAS: 189574-20-7
• 化学式: C₂₁H₂₄N₂O₄
• 分子量: 368.433
• InChiKey: BGPXLBACWHVXTA-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4,5-bis(N-benzylamide) 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 18.0h， 生成 (4S,5S)-benzyl[5-(benzylaminomethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]amine
  参考文献：
  名称：

  通过顺序加氢甲酰化/还原胺化合成酒石酸衍生的氮杂大环化合物作为不对称催化的潜在配体的荧光筛选

  摘要：

  通过铑催化的加氢甲酰基化合成包含酒石酸衍生的单元和芳基单元的氮杂大环，随后以串联或逐步方式进行还原胺化。在荧光发射实验中，一些大环化合物显示出对过渡金属（例如锌或铑）的螯合亲和力。

  DOI：

  10.1016/j.tetasy.2005.03.035
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 lithium hydroxide 、 草酰氯 、 18-冠醚-6 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 (4R,5R)-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4,5-bis(N-benzylamide)
  参考文献：
  名称：

  Efficient Synthetic Method forl-Tartaramides by Aminolysis of Reactive 2,3-O-Isopropylidene-L-tartaryl Chloride

  摘要：

  The reactive 2,3-O-isopropylidene-L-tartaryl chloride 4 was firstly synthesized from L-(+)-tartaric acid. Various chiral 2,3-O-isopropylidene-L-tartaramides 5 were prepared by aminolysis of the reactive L-tartaryl chloride 4 with primary and secondary amines.

  DOI：

  10.1080/00397919708003365

文献信息

• Fluorescence screening of tartaric acid-derived azamacrocycles synthesized via sequential hydroformylation/reductive amination as potential ligands for asymmetric catalysis
  作者：Goran Angelovski、Mark D. Keränen、Peter Eilbracht

  DOI：10.1016/j.tetasy.2005.03.035

  日期：2005.6

  Azamacrocycles containing a tartaric acid-derived unit and aryl units were synthesized via rhodium-catalyzed hydroformylation while the subsequent reductive amination was carried out in a tandem or stepwise fashion. Upon fluorescence emission experiments, some of the macrocycles showed chelating affinities toward transition metals such as zinc or rhodium.

  通过铑催化的加氢甲酰基化合成包含酒石酸衍生的单元和芳基单元的氮杂大环，随后以串联或逐步方式进行还原胺化。在荧光发射实验中，一些大环化合物显示出对过渡金属（例如锌或铑）的螯合亲和力。
• Synthesis of Chiral Aza Crown Ethers Having Exocyclic Hydroxy Groups and Their Use in Asymmetric Reduction of Ketones with Sodium Tetrahydridoborate
  作者：N. G. Luk'yanenko、A. V. Lobach、O. N. Leus

  DOI：10.1023/b:rujo.0000003201.57627.ee

  日期：2003.7

  New chiral diaza crown ethers with exocyclic hydroxy groups were synthesized by reactions of (2S,3S)-1,4-dibenzyloxy-2,3-bis(2-oxiranylmethoxy)butane with N,N'-dibenzyl-1,2-ethanediamine and (4S,5S)-4,5-bis(benzylaminomethyl)-2,2-dimethyl-1,3-dioxolane. Catalytic debenzylation of the products gave the corresponding derivatives having secondary amino groups. The obtained diaza crown ethers, as well as some known crown ethers, were used as asymmetric catalysts in the reduction of pinacolone and acetophenone with sodium tetrahydridoborate in methylene chloride. Depending on the catalyst structure, the optical yield of the reduction products ranged from 5 to 90%.
• Carbonylation of functionalized diamine diols to cyclic ureas: application to derivatives of DMP 450
  作者：Ampofo K. Darko、F. Chris Curran、Chloé Copin、Lisa McElwee-White

  DOI：10.1016/j.tet.2011.04.015

  日期：2011.6

  inhibitor DMP 450 has been achieved via W(CO)6/I2-catalyzed carbonylation of diamine intermediates. Carbonylations of related functionalized diamines to derivatives of the DMP 450 core structure were also examined. Selected diamine diol substrates could be converted to the cyclic urea core structure by catalytic carbonylation without protection of the diol functionality.

  HIV蛋白酶抑制剂DMP 450的环状脲核心结构的合成已经通过W（CO）6 / I 2催化的二胺中间体的羰基化而实现。还检查了相关的官能化二胺羰基化为DMP 450核心结构的衍生物。选定的二胺二醇底物可通过催化羰基化转化为环状脲核心结构，而无需保护二醇的功能。
• Efficient Synthetic Method for<scp>l</scp>-Tartaramides by Aminolysis of Reactive 2,3-<i>O</i>-Isopropylidene-<scp>L</scp>-tartaryl Chloride
  作者：Heung-Jin Choi、Mi-Ok Kwak、Hanchul Song

  DOI：10.1080/00397919708003365

  日期：1997.4

  The reactive 2,3-O-isopropylidene-L-tartaryl chloride 4 was firstly synthesized from L-(+)-tartaric acid. Various chiral 2,3-O-isopropylidene-L-tartaramides 5 were prepared by aminolysis of the reactive L-tartaryl chloride 4 with primary and secondary amines.