Benzyl 2-isocyanoethyl carbonate | 1355545-55-9

• 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: Benzyl 2-isocyanoethyl carbonate
• CAS: 1355545-55-9
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: SNATWNJJPHRJKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-缬氨酸 、 Benzyl 2-isocyanoethyl carbonate 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 96.0h， 生成 (9R,11S)-methyl 7-(tert-butoxycarbonyl)-9-(3,4-dimethoxyphenyl)-12-methyl-3,8-dioxo-1-phenyl-2,4-dioxa-7,10-diazatridecane-11-carboxylate
  参考文献：
  名称：

  An Approach to the Synthesis of Enantiopure Tetrahydroisoquinoline via a Key Asymmetric Ugi Reaction

  摘要：

  An approach to the synthesis of the multisubstituted tetrahydroisoquinoline featuring an asymmetric Ugi reaction of a-amino acid, aromatic aldehyde and an isocyanide has been developed. The promising utility of the strategy is demonstrated by a synthesis of an enantiopure functionalized 1,3-trans-tetrahydroiso-quinolin-4-ol from natural L-valine. The configuration of the two stereocenters at C-1 and C-4, generated in the Ugi reaction and Pomeranz-Fritsch-type cyclization separately, was controlled very well and determined by NMR studies.

  DOI：

  10.1055/s-0032-1317931

文献信息

• An Asymmetric Ugi Three-Component Reaction Induced by Chiral Cyclic Imines: Synthesis of Morpholin– or Piperazine–Keto-carboxamide Derivatives
  作者：Deguang Zhu、Liang Xia、Li Pan、Sheng Li、Ruijiao Chen、Yongren Mou、Xiaochuan Chen

  DOI：10.1021/jo2021967

  日期：2012.2.3

  4-oxazin-2-one substrates, as preformed cyclic aldimines and ketoimines, were employed to develop a new asymmetric Ugi three-component reaction for the first time. The Ugi reaction of the imines, isocyanides, and carboxylic acids opens an efficient access to novel morpholin-2-one-3-carboxamide compounds. The chiral imines showed promising stereoinduction for the new chiral center of the Ugi products, and

  一系列手性5,6-二氢-1,4-恶嗪-2-酮底物，如预先形成的环状醛亚胺和酮亚胺，首次用于开发新的不对称Ugi三组分反应。亚胺，异氰酸酯和羧酸的Ugi反应使人们可以有效地获得新型的吗啉-2-二-3-甲酰胺化合物。手性亚胺对Ugi产品的新手性中心显示出有希望的立体诱导，并且在大多数情况下获得了主要的反式异构体。添加一些路易斯酸或质子酸可以进一步提高非对映选择性，但通常会导致总收率下降。Ugi-3CR可以扩展到ketopiperazine-2-carboxamide衍生物的立体选择性合成。