methyl (2S)-2-[[(Z)-4-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]amino]but-2-enyl]amino]-4-methylpentanoate | 313969-87-8

• 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: methyl (2S)-2-[[(Z)-4-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]amino]but-2-enyl]amino]-4-methylpentanoate
• CAS: 313969-87-8
• 化学式: C₁₈H₃₄N₂O₄
• 分子量: 342.479
• InChiKey: JSGBKDLZZGRFGO-FLELRFNZSA-N

物化性质

• 沸点：
  417.1±45.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  methyl (2S)-2-[[(Z)-4-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]amino]but-2-enyl]amino]-4-methylpentanoate 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-[2-Methoxy-3-((S)-1-methoxycarbonyl-3-methyl-butyl)-2-oxo-2,3,4,7-tetrahydro-2λ⁵-[1,3,2]diazaphosphepin-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 108.0h， 生成 methyl (2S)-2-[[(Z)-4-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]amino]but-2-enyl]amino]-4-methylpentanoate
  参考文献：
  名称：

  空间上需要氨基酸的环状膦酰胺的合成。

  摘要：

  描述了C（2）-对称的1,4-二胺在氨基酸衍生的环状膦酰胺1-3的合成中的制备和利用。1,4-二胺是通过三种方法合成的：（i）氨基酸/富马酰氯偶联，然后进行酰胺还原；（ii）氨基酸/ 1,4-二胺偶联，然后进行酰胺还原；以及（iii）模板-支持的闭环复分解/水解序列。通过将C（2）对称的1,4-二胺缩合到P（III）中心，然后进行氧化来制备伪C（2）对称的环状膦酰胺1-3。

  DOI：

  10.1021/jo005545q

文献信息

• The Synthesis of Sterically Demanding Amino Acid-Derived Cyclic Phosphonamides
  作者：Kevin T. Sprott、Paul R. Hanson

  DOI：10.1021/jo005545q

  日期：2000.11.1

  4-diamines in the synthesis of amino acid-derived cyclic phosphonamides 1-3 are described. The 1,4-diamines are synthesized via three methods: (i) amino acid/fumaryl chloride coupling followed by amide reduction, (ii) amino acid/1,4-diamine coupling followed by amide reduction, and (iii) a template-supported ring-closing metathesis/hydrolysis sequence. The pseudo C(2)-symmetric cyclic phosphonamides 1-3 are

  描述了C（2）-对称的1,4-二胺在氨基酸衍生的环状膦酰胺1-3的合成中的制备和利用。1,4-二胺是通过三种方法合成的：（i）氨基酸/富马酰氯偶联，然后进行酰胺还原；（ii）氨基酸/ 1,4-二胺偶联，然后进行酰胺还原；以及（iii）模板-支持的闭环复分解/水解序列。通过将C（2）对称的1,4-二胺缩合到P（III）中心，然后进行氧化来制备伪C（2）对称的环状膦酰胺1-3。
• 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.