(S)-2-[(Z)-4-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylamino)-but-2-enylamino]-3-phenyl-propionic acid benzyl ester | 384824-20-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-2-[(Z)-4-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylamino)-but-2-enylamino]-3-phenyl-propionic acid benzyl ester
• 英文别名: benzyl (2S)-2-[[(Z)-4-[[(2S)-1-oxo-3-phenyl-1-phenylmethoxypropan-2-yl]amino]but-2-enyl]amino]-3-phenylpropanoate
• CAS: 384824-20-8
• 化学式: C₃₆H₃₈N₂O₄
• 分子量: 562.709
• InChiKey: LUFDFVUBTSVIOF-XLEBCTGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-[(Z)-4-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylamino)-but-2-enylamino]-3-phenyl-propionic acid benzyl ester 在 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (S)-2-[3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-2-oxo-2-phenyl-2,3,4,7-tetrahydro-2λ⁵-[1,3,2]diazaphosphepin-1-yl]-3-phenyl-propionic acid benzyl ester
  参考文献：
  名称：

  A Concise Route to Structurally Diverse DMP 323 Analogues via Highly Functionalized 1,4-Diamines

  摘要：

  [GRAPHICS]The utility of functionalized 1,4-diamines, produced via a temporary phosphorus tether (P-tether)/ring-closing metathesis (RCM)/hydrolysis sequence, is demonstrated in the synthesis of structurally diverse DMP 323 analogues. These 1,4-diamines are transformed into various seven-membered heterocycles via insertion of the appropriate nuclei "X". Subsequent derivatization generates heterocyclic diols that are similar in structure to DMP 323, a notable member of a class of highly potent inhibitors of HIV protease.

  DOI：

  10.1021/ol027074v
• 作为产物：
  描述：

  (S)-2-[3-((S)-1-Benzyloxycarbonyl-2-phenyl-ethyl)-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,3,2]diazaphosphepin-1-yl]-3-phenyl-propionic acid benzyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 以99%的产率得到(S)-2-[(Z)-4-((S)-1-Benzyloxycarbonyl-2-phenyl-ethylamino)-but-2-enylamino]-3-phenyl-propionic acid benzyl ester
  参考文献：
  名称：

  A Temporary Phosphorus Tether/Ring-Closing Metathesis Strategy to Functionalized 1,4-Diamines

  摘要：

  [GRAPHICS]The synthesis of 1,4-diamines containing the (Z)-1,4-diaminobut-2-ene subunit via a temporary phosphorus tether/RCM strategy is described. We have developed a new method utilizing phosphorus nuclei as suitable temporary tethers for the coupling of nonracemic allylic amines. This approach allows for the generation of C-2-symmetric and unsymmetric 1,4-diamines 1-3, which may have considerable synthetic and biological utility. This represents the first synthetic pathway for the expedient coupling of two amines via a temporary tether approach.

  DOI：

  10.1021/ol016828n