(R)-2-Allyloxycarbonylamino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester | 147240-38-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-2-Allyloxycarbonylamino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester
• CAS: 147240-38-8
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: NJMCTFPJQLINIG-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-2-Allyloxycarbonylamino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester 在 四(三苯基膦)钯 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以96%的产率得到(R)-2-Amino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  An effective synthesis of scalemic 3,5,5-trisubstituted pyrrolin-4-ones

  摘要：

  A new two-step method employs the intramolecular cyclization of metalated imino esters for the construction of scalemic 3,5,5-trisubstituted pyrrolin-4-ones (4). The imino esters in turn derive from alpha-disubstituted amino acids, the latter readily available via a new protocol exploiting the enantioretentive alkylation of oxazolidinones.

  DOI：

  10.1016/s0040-4039(00)60058-8
• 作为产物：
  描述：

  D-苯丙氨酸 在 sodium hydroxide 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 450.25h， 生成 (R)-2-Allyloxycarbonylamino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based .beta.-Strand Peptidomimetics

  摘要：

  The de novo design and synthesis of a novel non-peptide scaffolding for beta-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iterative construction of the pyrrolinones exploits a highly efficient cyclization of metalloimines, the latter derived from C-terminal aldehydes and readily available alpha-substituted alpha-amino ester building blocks. As predicted by interactive computer modeling and confirmed by X-ray crystallography, the polypyrrolinones present the side chains and carbonyl hydrogen-bond accepters in a solid-state conformation which mimics polypeptide beta-sheets. Importantly, the enaminone NH protons form hydrogen bonds both intramolecularly, stabilizing the beta-strand conformation, and intermolecularly, promoting sheet formation. The presence or absence of the nitrogen protecting group controlled antiparallel versus parallel sheet formation.

  DOI：

  10.1021/ja00101a017

文献信息

• A second-generation synthesis of scalemic 3,5,5-trisubstituted pyrrolin-4-ones: Incorporation of functionalized amino acid side-chains
  作者：Amos B. Smith、Andrew B. Benowitz、David A. Favor、Paul A. Sprengeler、Ralph Hirschmann

  DOI：10.1016/s0040-4039(97)00752-1

  日期：1997.6

  To access mimics of peptidal β-strands (1), scalemic 3,5,5-trisubstituted pyrrolin-4-ones bearing the tyrosine, serine, and lysine side-chains have been generated via cyclization of metalated imino esters and deprotection. The functionalized imino esters were prepared by asymmetric alkylation of a common oxazolidinone precursor (2) derived from L-prenylglycine.

  为了获得肽β链的模拟物（1），通过金属化亚氨基酯的环化和脱保护作用，产生了带有酪氨酸，丝氨酸和赖氨酸侧链的3，5，5-三取代的吡咯啉-4-酮。通过衍生自L-异戊烯基甘氨酸的常见恶唑烷酮前体（2）的不对称烷基化制备官能化的亚氨基酯。