(2R,3R,4R) 2,3-epoxy-4-methyl oct-6-ynoic acid | 158220-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R,3R,4R) 2,3-epoxy-4-methyl oct-6-ynoic acid
• 英文别名: (2R,3R)-3-[(2R)-hex-4-yn-2-yl]oxirane-2-carboxylic acid
• CAS: 158220-65-6
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: XHRJSXURSWVEKO-BWZBUEFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R) 2,3-epoxy-4-methyl oct-6-ynoic acid 在 氨 、 lithium 作用下， 反应 0.08h， 生成 (2S,3R,4R,6E)-3-羟基-4-甲基-2-(甲基氨基)-6-辛烯酸
  参考文献：
  名称：

  A short synthesis of the unusual amino acid of cyclosporine (4R)-4-[(E)-2-butenyl]-4,N-dimethyl-L-threonine (MeBmt)

  摘要：

  MeBmt 1 was prepared in four steps from the optically pure (2Z, 4R) 4-methyloct-6-yn-2-en-1-ol 8, Z allylic alcohol containing an alkynyl group at the gamma position. The two stereogenic centers C-2 and C-3 in the product were controlled using Sharpless' epoxidation and subsequent ring opening at C-2 of the epoxy acid 10 with methylamine.

  DOI：

  10.1016/0957-4166(94)80034-0
• 作为产物：
  描述：

  (2S,3R,4R) 2,3-epoxy-4-methyl oct-6-yn-1-ol 在 pyridium dichromate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以75%的产率得到(2R,3R,4R) 2,3-epoxy-4-methyl oct-6-ynoic acid
  参考文献：
  名称：

  A short synthesis of the unusual amino acid of cyclosporine (4R)-4-[(E)-2-butenyl]-4,N-dimethyl-L-threonine (MeBmt)

  摘要：

  MeBmt 1 was prepared in four steps from the optically pure (2Z, 4R) 4-methyloct-6-yn-2-en-1-ol 8, Z allylic alcohol containing an alkynyl group at the gamma position. The two stereogenic centers C-2 and C-3 in the product were controlled using Sharpless' epoxidation and subsequent ring opening at C-2 of the epoxy acid 10 with methylamine.

  DOI：

  10.1016/0957-4166(94)80034-0

文献信息

• A short synthesis of the unusual amino acid of cyclosporine (4R)-4-[(E)-2-butenyl]-4,N-dimethyl-L-threonine (MeBmt)
  作者：Monique Savignac、Jean-Olivier Durand、Jean-Pierre Genêt

  DOI：10.1016/0957-4166(94)80034-0

  日期：1994.4

  MeBmt 1 was prepared in four steps from the optically pure (2Z, 4R) 4-methyloct-6-yn-2-en-1-ol 8, Z allylic alcohol containing an alkynyl group at the gamma position. The two stereogenic centers C-2 and C-3 in the product were controlled using Sharpless' epoxidation and subsequent ring opening at C-2 of the epoxy acid 10 with methylamine.