(1S)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)ethyl isocyanide | 1101195-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)ethyl isocyanide
• 英文别名: CN-Ala-OBO；1-[(1S)-1-isocyanoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
• CAS: 1101195-46-3
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: WMRMBPNNZSKPDO-UEJVZZJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  32
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)ethyl isocyanide 在 叠氮基三甲基硅烷 作用下， 以 2,2,2-三氟乙醇 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  手性α-（四唑-1-基）取代的羧酸的合成

  摘要：

  由相应的α-异氰基OBO酯和叠氮化三甲基甲硅烷基合成光学活性α-（四唑-1-基）取代的羧酸OBO酯，收率高达92％。随后的酸性水解没有差向异构发生，并且使得可以以高达89％的收率制备对映体纯的α-（四唑-1-基）取代的羧酸。

  DOI：

  10.1016/j.mencom.2018.07.007
• 作为产物：
  描述：

  [(1S)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)ethyl]formamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(1S)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)ethyl isocyanide
  参考文献：
  名称：

  Nonracemizable Isocyanoacetates for Multicomponent Reactions

  摘要：

  Chiral ortho esters of a-isocyano acids were synthesized from commercially available Cbz-protected alpha-amino acids. These compounds are stable toward racemization in the Ugi 4CC in contrast to known esters of alpha-isocyano acids. Applying them in Ugi 4CC with subsequent deprotection gives access to dipeptides with preserved configuration at the C-terminal amino acid.

  DOI：

  10.1021/jo802420c

文献信息

• Tetrazole-Substituted Five, Six, and Seven-Membered Cyclic Amines Bearing Perfluoroalkyl Groups - Efficient Synthesis by Azido-Ugi Reaction
  作者：Olga I. Shmatova、Valentine G. Nenajdenko

  DOI：10.1002/ejoc.201300861

  日期：2013.10

  azido-Ugi reactions was studied. It was shown that the reaction allows access to five-, six- and seven-membered perfluoroalkylated cyclic amines connected to a tetrazole ring. The scope and limitations of this approach are discussed. When benzyl isocyanide was used in the azido-Ugi reaction, it was shown that the tetrazole products could easily be debenzylated by catalytic hydrogenation to form 1H-tetrazoles

  研究了全氟烷基化环亚胺在叠氮基-Ugi反应中的应用。结果表明，该反应允许获得与四唑环相连的五元、六元和七元全氟烷基化环胺。讨论了这种方法的范围和局限性。当在叠氮基-Ugi 反应中使用苄基异氰化物时，表明四唑产物可以很容易地通过催化氢化脱苄基，以优异的产率形成 1H-四唑。
• Diastereoselectivity of Azido-Ugi Reaction with Secondary Amines. Stereoselective Synthesis of Tetrazole Derivatives
  作者：Danil P. Zarezin、Victor N. Khrustalev、Valentine G. Nenajdenko

  DOI：10.1021/acs.joc.7b00611

  日期：2017.6.16

  diastereoselectivity of azido-Ugi reaction with cyclic amines was investigated. It was found that the reaction with α-substituted five- to seven-membered cyclic amines proceeds very efficiently to provide high control of diastereoselectivity (≤100% de) under mild conditions. Target tetrazole-derived products were isolated in excellent yields (≤98%). The reaction has a broad scope in terms of its amine, aldehyde, and

  研究了叠氮基-Ugi与环胺的非对映选择性。发现与α-取代的五元至七元环胺的反应非常有效地进行，以在温和的条件下高度控制非对映选择性（≤100％de）。分离出目标四唑衍生产品，收率极高（≤98％）。就胺，醛和异氰酸酯的性质而言，该反应具有广泛的范围。发现反应的非对映选择性取决于起始环胺的环大小。刚性更高的哌啶提供最高的反应选择性。使用苄基异氰化物，可以通过氢解将制备的N-苄基四唑脱保护以形成相应的NH四唑。