(R)-2-Amino-2-benzyl-5-methyl-hexanoic acid methyl ester | 847020-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-Amino-2-benzyl-5-methyl-hexanoic acid methyl ester
• 英文别名: methyl (2R)-2-amino-2-benzyl-5-methylhexanoate
• CAS: 847020-85-3
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: DCPIAAMZKVCAGJ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-2-benzyl-5-methyl-hexanoic acid methyl ester 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 甲苯 、 苯 为溶剂， 反应 2.25h， 生成 (2R,5'S,5''R,5'''R)-5'-(4-Azido-butyl)-4,5'',5'''-tribenzyl-2-isopropyl-5'''-(3-methyl-butyl)-1,2,1',5',1'',5'',1''',5'''-octahydro-[2,3';5',3'';5'',3''']quaterpyrrole-3,4',4'',4'''-tetraone
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974
• 作为产物：
  描述：

  (R)-2-Amino-2-benzyl-5-methyl-hex-4-enoic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 22.0h， 以93%的产率得到(R)-2-Amino-2-benzyl-5-methyl-hexanoic acid methyl ester
  参考文献：
  名称：

  Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics

  摘要：

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.

  DOI：

  10.1021/ol0476974

文献信息

• Design, Synthesis, and Binding Affinities of Pyrrolinone-Based Somatostatin Mimetics
  作者：Amos B. Smith、Adam K. Charnley、Eugen F. Mesaros、Osamu Kikuchi、Wenyong Wang、Andrew Benowitz、Chi-Lien Chu、Jin-Jye Feng、Kuo-Hsin Chen、Atsui Lin、Fong-Chi Cheng、Laurie Taylor、Ralph Hirschmann

  DOI：10.1021/ol0476974

  日期：2005.2.1

  Tetrapyrrolinone somatostatin (SRIF) mimetics (cf. 1), based on a heterochiral (D,L-Mixed) pyrrolinone scaffold, were designed, synthesized, and evaluated for biological activity. The iterative synthetic sequence, incorporating the requisite functionalized coded and noncoded amino acid side chains, comprised a longest linear synthetic sequence of 23 steps. Binding affinities at two somatostatin receptor subtypes (hsst 4 and 5) reveal micromolar activity, demonstrating that the D,L-Mixed pyrrolinone scaffold can be employed to generate functional mimetics of peptide beta-turns.