(E)-(R)-2-Amino-hex-4-enoic acid methyl ester | 81136-82-5

• 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: (E)-(R)-2-Amino-hex-4-enoic acid methyl ester
• 英文别名: methyl (E,2R)-2-aminohex-4-enoate
• CAS: 81136-82-5
• 化学式: C₇H₁₃NO₂
• 分子量: 143.186
• InChiKey: KWXSKNMYRRUMDX-FCJGRKLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (E)-(R)-2-Amino-hex-4-enoic acid methyl ester 在 disodium hydrogenphosphate 、 lithium aluminium tetrahydride 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 10.0h， 生成 2-(S)-methyl-5-(S),9-(R)-dioxa-8-(S)-aza-tricyclo[5.2.1.0^3,8]decan-4-one
  参考文献：
  名称：

  Syntheses of the cylindrospermopsin alkaloids

  摘要：

  An intramolecular 1,3-dipolar cycloaddition has efficiently constructed the A-ring portions of the cylindrospermopsin alkaloids. A nitro-aldol addition of an elaborated nitroalkane to a pyrimidine aldehyde followed by an intramolecular reductive guanidinylation has enabled the syntheses of all three alkaloids in this family in 18-19 steps. We report the first asymmetric synthesis of cylindrospermopsin, unambiguously assigning its absolute configuration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.044
• 作为产物：
  描述：

  (3R,5R,6S)-3-(but-2-enyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylic acid tert-butyl ester 在 氨 、 lithium 、 乙酰氯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 0.5h， 生成 (E)-(R)-2-Amino-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  Syntheses of the cylindrospermopsin alkaloids

  摘要：

  An intramolecular 1,3-dipolar cycloaddition has efficiently constructed the A-ring portions of the cylindrospermopsin alkaloids. A nitro-aldol addition of an elaborated nitroalkane to a pyrimidine aldehyde followed by an intramolecular reductive guanidinylation has enabled the syntheses of all three alkaloids in this family in 18-19 steps. We report the first asymmetric synthesis of cylindrospermopsin, unambiguously assigning its absolute configuration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.02.044

文献信息

• Syntheses of the cylindrospermopsin alkaloids
  作者：Ryan E. Looper、Maria T.C. Runnegar、Robert M. Williams

  DOI：10.1016/j.tet.2006.02.044

  日期：2006.5

  An intramolecular 1,3-dipolar cycloaddition has efficiently constructed the A-ring portions of the cylindrospermopsin alkaloids. A nitro-aldol addition of an elaborated nitroalkane to a pyrimidine aldehyde followed by an intramolecular reductive guanidinylation has enabled the syntheses of all three alkaloids in this family in 18-19 steps. We report the first asymmetric synthesis of cylindrospermopsin, unambiguously assigning its absolute configuration. (c) 2006 Elsevier Ltd. All rights reserved.