5-benzhydryl 1-tert-butyl 2-oxopentanedioate | 1585241-68-4

• 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: 5-benzhydryl 1-tert-butyl 2-oxopentanedioate
• 英文别名: 5-O-benzhydryl 1-O-tert-butyl 2-oxopentanedioate
• CAS: 1585241-68-4
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: IDVHLUALTMBHFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzhydryl 1-tert-butyl 2-oxopentanedioate 在 氯化亚砜 、 Ni(OAc)2-(H₂O)4-(S,S)-N,N'-dibenzylcyclohexane-1,2-diamine complex 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 75.0 ℃ 、6.21 MPa 条件下， 反应 3.5h， 生成 methyl 5-((3S,4S,5R)-5-(tert-butoxycarbonyl)-4-(2-methoxy-2-oxoethyl)pyrrolidin-3-yl)-6-methoxypicolinate
  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：

  二苯基重氮甲烷 在 臭氧 、 sodium iodide 作用下， 以 乙醚 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 59.0h， 生成 5-benzhydryl 1-tert-butyl 2-oxopentanedioate
  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.