(S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester | 155012-89-8

• 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)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester
• 英文别名: ethyl (2R)-2-[[(2S)-2-(1,3-dioxoisoindol-2-yl)-6-hydroxyhexanoyl]amino]-3-phenylpropanoate
• CAS: 155012-89-8
• 化学式: C₂₅H₂₈N₂O₆
• 分子量: 452.507
• InChiKey: UASCGOXCZXTEEV-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 144.25h， 生成 <3R-(3α,6α)>-tetrahydro-2,5-dioxo-3-(phenylmethyl)-6-phthalimidooxazolo<3,2-a>azepine-2,5(3H,6H)-dione
  参考文献：
  名称：

  Peptidomimetic Synthesis: A Novel, Highly Stereoselective Route to Substituted Freidinger Lactams

  摘要：

  New methodology for the synthesis of substituted seven-membered lactams 3 has been developed. This method allows for the stereoselective introduction of substituents at the C-7 position of the azepinone ring as well as a to the acetic acid side chain. Dehydrative cyclization of dipeptidyl aldehydes 11 affords the corresponding bicyclic fused lactams 12 in good yield and high stereoselectivity. Lewis acid catalyzed reduction of 12 with triethylsilane provides azepinones 16 in homochiral form. Introduction of substituents at the C-7 position was effected by treatment of 12 with various alkyl nucleophiles. The resulting azepinones may be viewed as conformationally restricted dipeptidomimetic surrogates.

  DOI：

  10.1021/ja00085a014
• 作为产物：
  描述：

  L-6-羟基正亮氨酸 在 N-甲基吗啉 、 sodium carbonate 、 1-羟基苯并三唑一水物 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 (S)-N-(6-hydroxy-1-oxo-2-phthalimidohexyl)-D-phenylalanine ethyl ester
  参考文献：
  名称：

  Peptidomimetic Synthesis: A Novel, Highly Stereoselective Route to Substituted Freidinger Lactams

  摘要：

  New methodology for the synthesis of substituted seven-membered lactams 3 has been developed. This method allows for the stereoselective introduction of substituents at the C-7 position of the azepinone ring as well as a to the acetic acid side chain. Dehydrative cyclization of dipeptidyl aldehydes 11 affords the corresponding bicyclic fused lactams 12 in good yield and high stereoselectivity. Lewis acid catalyzed reduction of 12 with triethylsilane provides azepinones 16 in homochiral form. Introduction of substituents at the C-7 position was effected by treatment of 12 with various alkyl nucleophiles. The resulting azepinones may be viewed as conformationally restricted dipeptidomimetic surrogates.

  DOI：

  10.1021/ja00085a014

文献信息

• Peptidomimetic Synthesis: A Novel, Highly Stereoselective Route to Substituted Freidinger Lactams
  作者：Jeffrey A. Robl、Maria P. Cimarusti、Ligaya M. Simpkins、Harold N. Weller、Yolanda Y. Pan、Mary Malley、John D. DiMarco

  DOI：10.1021/ja00085a014

  日期：1994.3

  New methodology for the synthesis of substituted seven-membered lactams 3 has been developed. This method allows for the stereoselective introduction of substituents at the C-7 position of the azepinone ring as well as a to the acetic acid side chain. Dehydrative cyclization of dipeptidyl aldehydes 11 affords the corresponding bicyclic fused lactams 12 in good yield and high stereoselectivity. Lewis acid catalyzed reduction of 12 with triethylsilane provides azepinones 16 in homochiral form. Introduction of substituents at the C-7 position was effected by treatment of 12 with various alkyl nucleophiles. The resulting azepinones may be viewed as conformationally restricted dipeptidomimetic surrogates.