(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-hydroxy-3-(4-methoxyphenylamino)-3-phenylpropanoate | 950586-04-6

• 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
• 英文名称: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-hydroxy-3-(4-methoxyphenylamino)-3-phenylpropanoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (2R,3S)-2-hydroxy-3-(4-methoxyanilino)-3-phenylpropanoate
• CAS: 950586-04-6
• 化学式: C₂₆H₃₅NO₄
• 分子量: 425.568
• InChiKey: XZSVVCBGHRUMQA-HMXZAHMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-hydroxy-3-(4-methoxyphenylamino)-3-phenylpropanoate 在 咪唑 、 ammonium cerium(IV) nitrate 、 甲基溴化镁 、 四丁基氟化铵 、 水 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.25h， 生成 (3R,4S)-3-羟基-4-苯基-2-氮杂环丁酮
  参考文献：
  名称：

  Asymmetric synthesis of 3-amino-2-hydroxyalkanoates by Mannich reaction of menthyl acetate with imines and subsequent oxidation

  摘要：

  Lithium amide-assisted Mannich-type reaction of menthyl acetate-derived lithium enolate with PMP-arylaldimines and subsequent in situ oxidation with oxaziridine gave syn-3-amino-3-aryl-2-hydroxypropanoates with high syn-selectivity and diastereoselectivity (with respect to menthyl moiety) in a one-pot procedure. Propargyl aldehyde-derived imines were also stereoselectively converted to the Mannich-oxidation products by a stepwise procedure. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.031
• 作为产物：
  描述：

  乙酸薄荷酯 、 4-methoxy-N-[(E)-phenylmethylidene]aniline 以205 mg的产率得到(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,3S)-2-hydroxy-3-(4-methoxyphenylamino)-3-phenylpropanoate
  参考文献：
  名称：

  Asymmetric synthesis of 3-amino-2-hydroxyalkanoates by Mannich reaction of menthyl acetate with imines and subsequent oxidation

  摘要：

  Lithium amide-assisted Mannich-type reaction of menthyl acetate-derived lithium enolate with PMP-arylaldimines and subsequent in situ oxidation with oxaziridine gave syn-3-amino-3-aryl-2-hydroxypropanoates with high syn-selectivity and diastereoselectivity (with respect to menthyl moiety) in a one-pot procedure. Propargyl aldehyde-derived imines were also stereoselectively converted to the Mannich-oxidation products by a stepwise procedure. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.031