tert-butyl 5-((4-methoxybenzyl)oxy)-2-oxopentanoate | 1585241-74-2

• 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: tert-butyl 5-((4-methoxybenzyl)oxy)-2-oxopentanoate
• 英文别名: Tert-butyl 5-[(4-methoxyphenyl)methoxy]-2-oxopentanoate；tert-butyl 5-[(4-methoxyphenyl)methoxy]-2-oxopentanoate
• CAS: 1585241-74-2
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: HIMZQLASUSPXMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 5-((4-methoxybenzyl)oxy)-2-oxopentanoate 在 碘苯二乙酸 、 2-azaadamantane-N-oxyl 、 Ni(OAc)2-(H₂O)4-(S,S)-N,N'-dibenzylcyclohexane-1,2-diamine complex 、 水 、 氢气 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 aq. phosphate buffer 、 二氯甲烷 、 异丙醇 为溶剂， -10.0~75.0 ℃ 、4.83 MPa 条件下， 反应 25.0h， 生成 2-((2R,3S,4S)-1-((benzyloxy)carbonyl)-2-(tert-butoxycarbonyl)-4-(2-(tert-butoxycarbonyl)-6-methoxypyridin-3-yl)-pyrrolidin-3-yl)acetic acid
  参考文献：
  名称：

  Practical Total Syntheses of Acromelic Acids A and B

  摘要：

  Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro-excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni-catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.

  DOI：

  10.1021/ol500529w
• 作为产物：
  描述：

  1-[(3-iodopropoxy)methyl]-4-methoxybenzene 在 2-benzenesulfonyl-3-phenyl-1,2-oxaziridine 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成 tert-butyl 5-((4-methoxybenzyl)oxy)-2-oxopentanoate
  参考文献：
  名称：

  Practical Total Syntheses of Acromelic Acids A and B

  摘要：

  Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro-excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni-catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.

  DOI：

  10.1021/ol500529w

文献信息

• Practical Total Syntheses of Acromelic Acids A and B
  作者：Hitoshi Ouchi、Aya Asahina、Tomohiro Asakawa、Makoto Inai、Yoshitaka Hamashima、Toshiyuki Kan

  DOI：10.1021/ol500529w

  日期：2014.4.4

  Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro-excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni-catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.