[1R-(4-cyanomethylene-6R-naphthalen-2-ylethynyl-tetrahydro-pyran-2R-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester | 623143-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [1R-(4-cyanomethylene-6R-naphthalen-2-ylethynyl-tetrahydro-pyran-2R-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
• CAS: 623143-80-6
• 化学式: C₃₂H₃₂N₂O₃
• 分子量: 492.618
• InChiKey: IRYPPEFYYJUMDE-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  37.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.35
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [1R-(4-cyanomethylene-6R-naphthalen-2-ylethynyl-tetrahydro-pyran-2R-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 在 Wilkinson's catalyst 氢气 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 {1R-[4-cyanomethyl-6S-(2-naphthalen-2-yl-ethyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester 、 {1R-[4-cyanomethyl-6S-(2-naphthalen-2-yl-ethyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors

  摘要：

  We have prepared novel peptidomimetics based on a 2,4,6-trisubstituted tetrahydropyran. This scaffold was constructed in an isosteric transformation using conceptual constraints imposed on a tripeptide moiety involving O-i'-C-1(+1)gamma and O-i'-Ni+2 formal cyclization modes. A series of regioselective transformations commencing with a substituted dihydropyran-4-one readily provided the required analogues. Specific tetrahydropyrane analogues modeled on PheArgTrp as a truncated version of the melanocortin receptor message sequence, showed activity at the melanocortin receptors MC4R and MC1R. Thus, the 2,4,6-trisubstituted tetrahydropyran scaffold has provided a potentially useful peptidomimetic lead, and conceptual cyclization of peptide moieties can offer a valuable design strategy in peptidomimetic research. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00274-8
• 作为产物：
  描述：

  2-乙基萘 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 [1R-(4-cyanomethylene-6R-naphthalen-2-ylethynyl-tetrahydro-pyran-2R-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Novel tetrahydropyran-based peptidomimetics from a bioisosteric transformation of a tripeptide. Evidence of their activity at melanocortin receptors

  摘要：

  We have prepared novel peptidomimetics based on a 2,4,6-trisubstituted tetrahydropyran. This scaffold was constructed in an isosteric transformation using conceptual constraints imposed on a tripeptide moiety involving O-i'-C-1(+1)gamma and O-i'-Ni+2 formal cyclization modes. A series of regioselective transformations commencing with a substituted dihydropyran-4-one readily provided the required analogues. Specific tetrahydropyrane analogues modeled on PheArgTrp as a truncated version of the melanocortin receptor message sequence, showed activity at the melanocortin receptors MC4R and MC1R. Thus, the 2,4,6-trisubstituted tetrahydropyran scaffold has provided a potentially useful peptidomimetic lead, and conceptual cyclization of peptide moieties can offer a valuable design strategy in peptidomimetic research. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00274-8