2-甲基-2-丙基[(2S)-1-氧代-5-己烯-2-基]氨基甲酸酯 | 624743-18-6

• 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
• 中文名称: 2-甲基-2-丙基[(2S)-1-氧代-5-己烯-2-基]氨基甲酸酯
• 英文名称: N-butoxycarbonyl homoallylglycinal
• 英文别名: tert-butyl N-[(2S)-1-oxohex-5-en-2-yl]carbamate
• CAS: 624743-18-6
• 化学式: C₁₁H₁₉NO₃
• 分子量: 213.277
• InChiKey: CQHQSFLXHJTURA-VIFPVBQESA-N

物化性质

• 沸点：
  303.1±42.0 °C(Predicted)
• 密度：
  0.990±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲基-2-丙基[(2S)-1-氧代-5-己烯-2-基]氨基甲酸酯 在 4-二甲氨基吡啶 四氢化物钛 、 Grubbs catalyst first generation 、 TEA 、 氢气 、 铜 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hexamethyldisilazane 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 生成 [(3S,6S,13S)-3-Methyl-13-((2S,4R)-4-methyl-5-oxo-tetrahydro-furan-2-yl)-2,5-dioxo-1,4-diaza-cyclotridec-6-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Macrocyclic peptidomimetic inhibitors of β-secretase (BACE): First X-ray structure of a macrocyclic peptidomimetic-BACE complex

  摘要：

  The synthesis of novel macrocyclic peptidomimetic inhibitors of the enzyme BACE1 is described. These macrocycles are derived from a hydroxypthylene core structure. Compound 7 was co-crystallized with BACE1 and the X-ray structure of the complex elucidated at 1.6 angstrom resolution. This molecule inhibits the production of the A beta peptide in HEK293 cells overexpressing APP751sw. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.003
• 作为产物：
  描述：

  (S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 caesium carbonate 、 氯甲酸异丁酯 作用下， 生成 2-甲基-2-丙基[(2S)-1-氧代-5-己烯-2-基]氨基甲酸酯
  参考文献：
  名称：

  Macrocyclic peptidomimetic inhibitors of β-secretase (BACE): First X-ray structure of a macrocyclic peptidomimetic-BACE complex

  摘要：

  The synthesis of novel macrocyclic peptidomimetic inhibitors of the enzyme BACE1 is described. These macrocycles are derived from a hydroxypthylene core structure. Compound 7 was co-crystallized with BACE1 and the X-ray structure of the complex elucidated at 1.6 angstrom resolution. This molecule inhibits the production of the A beta peptide in HEK293 cells overexpressing APP751sw. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.09.003

文献信息

• Application of samarium diiodide (SmI₂)-induced reduction of γ-acetoxy-α,β-enoates with α-specific kinetic electrophilic trapping for the synthesis of amino acid derivatives
  作者：Akira Otaka、Akira Yukimasa、Junko Watanabe、Yoshikazu Sasaki、Sinya Oishi、Hirokazu Tamamura、Nobutaka Fujii

  DOI：10.1039/b303718e

  日期：——

  γ-Acetoxy-α,β-enoates were easily reduced by samarium diiodide (SmI2) in THF to generate samarium dienolates which were kinetically trapped with ease at their α-positions by electrophiles (proton, aldehydes or ketones) to yield (E)-alkene dipeptide isosteres or γ-amino acid derivatives in high chemical yields.

  γ-乙酰氧基-α,β-烯酸酯很容易被 THF 中的二碘化钐 (SmI2) 还原，生成二烯酸钐，后者在动力学上很容易被亲电子试剂（质子、醛或酮）捕获在其 α-位置，从而产生 (E )-烯烃二肽电子等排体或γ-氨基酸衍生物的化学产率很高。
• Macrocyclic peptidomimetic inhibitors of β-secretase (BACE): First X-ray structure of a macrocyclic peptidomimetic-BACE complex
  作者：Isabel Rojo、José Alfredo Martín、Howard Broughton、David Timm、Jon Erickson、Hsiu-Chiung Yang、James R. McCarthy

  DOI：10.1016/j.bmcl.2005.09.003

  日期：2006.1

  The synthesis of novel macrocyclic peptidomimetic inhibitors of the enzyme BACE1 is described. These macrocycles are derived from a hydroxypthylene core structure. Compound 7 was co-crystallized with BACE1 and the X-ray structure of the complex elucidated at 1.6 angstrom resolution. This molecule inhibits the production of the A beta peptide in HEK293 cells overexpressing APP751sw. (c) 2005 Elsevier Ltd. All rights reserved.