(R)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)(phenyl)methylformamide | 1101195-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)(phenyl)methylformamide
• 英文别名: OHCNH-Phg-OBO；N-[(R)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-phenylmethyl]formamide
• CAS: 1101195-43-0
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: GIULXEKACOJMNQ-IYXRBSQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)(phenyl)methylformamide 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(R)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)(phenyl)methyl 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
• 作为产物：
  描述：

  H2N-D-Phg-OBO 、 甲乙酐 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 0.08h， 以92%的产率得到(R)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)(phenyl)methylformamide
  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

• Nonracemizable Isocyanoacetates for Multicomponent Reactions
  作者：Alexander G. Zhdanko、Valentine G. Nenajdenko

  DOI：10.1021/jo802420c

  日期：2009.1.16

  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.