methyl (2S)-2-[[(Z,4S)-4-amino-5-methylhex-2-enyl]amino]-4-methylpentanoate | 384824-25-3

• 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: methyl (2S)-2-[[(Z,4S)-4-amino-5-methylhex-2-enyl]amino]-4-methylpentanoate
• CAS: 384824-25-3
• 化学式: C₁₄H₂₈N₂O₂
• 分子量: 256.389
• InChiKey: HHKPNTFUSYIRSK-FAVCKAPTSA-N

物化性质

• 沸点：
  342.6±37.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(Z,4S)-4-amino-5-methylhex-2-enyl]amino]-4-methylpentanoate 在 四氧化锇 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 (S)-2-((4S,5S,6R)-3-Benzyl-5,6-dihydroxy-4-isopropyl-2-oxo-[1,3]diazepan-1-yl)-4-methyl-pentanoic acid methyl 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：

  N-allyl (L)-leucine methyl ester 在 盐酸 、 4-二甲氨基吡啶 、 Grubbs catalyst first generation 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.08h， 生成 methyl (2S)-2-[[(Z,4S)-4-amino-5-methylhex-2-enyl]amino]-4-methylpentanoate
  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

文献信息

• A Temporary Phosphorus Tether/Ring-Closing Metathesis Strategy to Functionalized 1,4-Diamines
  作者：Kevin T. Sprott、Matthew D. McReynolds、Paul R. Hanson

  DOI：10.1021/ol016828n

  日期：2001.11.1

  [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.
• A Concise Route to Structurally Diverse DMP 323 Analogues via Highly Functionalized 1,4-Diamines
  作者：Matthew D. McReynolds、Kevin T. Sprott、Paul R. Hanson

  DOI：10.1021/ol027074v

  日期：2002.12.1

  [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.