N-[(1RS,2RS)-2-hydroxy-1-hydroxymethyl-2-(4-methoxy-phenyl)-ethyl]-acetamide | 74020-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[(1RS,2RS)-2-hydroxy-1-hydroxymethyl-2-(4-methoxy-phenyl)-ethyl]-acetamide
• 英文别名: (1RS,2RS)-2-Acetylamino-1-(4-methoxy-phenyl)-propan-1,3-diol；N-[(1RS,2RS)-2-Hydroxy-1-hydroxymethyl-2-(4-methoxy-phenyl)-aethyl]-acetamid；N-[(1S,2S)-1,3-dihydroxy-1-(4-methoxyphenyl)propan-2-yl]acetamide
• CAS: 74020-65-8
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: FTCKZMKSDJVBHN-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(1RS,2RS)-2-hydroxy-1-hydroxymethyl-2-(4-methoxy-phenyl)-ethyl]-acetamide 在 盐酸 作用下， 生成 (1RS,2RS)-2-amino-1-(4-methoxy-phenyl)-propane-1,3-diol
  参考文献：
  名称：

  Buu-Hoi et al., Journal of the Chemical Society, 1951, p. 255

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[1-hydroxymethyl-2-(4-methoxy-phenyl)-2-oxo-ethyl]-acetamide 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 N-[(1RS,2RS)-2-hydroxy-1-hydroxymethyl-2-(4-methoxy-phenyl)-ethyl]-acetamide
  参考文献：
  名称：

  Buu-Hoi et al., Journal of the Chemical Society, 1951, p. 255

  摘要：

  DOI：

文献信息

• Chloromycetin.¹ The Synthesis of p-Phenoxy and p-Methoxy Compounds
  作者：Mildred C. Rebstock、Elizabeth L. Pfeiffer

  DOI：10.1021/ja01133a001

  日期：1952.7
• Diastereoselective synthesis of substituted 2-amino-1,3-propanediols from Morita-Baylis-Hillman adducts
  作者：Paulo H. S. Paioti、Patrícia Rezende、Fernando Coelho

  DOI：10.1590/s0103-50532012000200014

  日期：——

  We report herein a new diastereoselective approach to substituted 2-amino-1,3-propanediols with anti relative stereochemistry from Morita-Baylis-Hillman (MBH) adducts. These structural moieties have been used as intermediates for the synthesis of several compounds with relevant pharmacological and commercial interest. In this strategy, substituted anti 2-amino-1,3-propanediols were readily prepared via ozonolysis of allylic diols obtained from MBH adducts, followed by a diastereoselective reductive amination of the substituted 2-oxo-1,3-propanediols. To demonstrate the synthetic utility of these aminodiols, they were transformed into substituted oxazolidin-2-ones, which were also used in the indirect determination of the relative stereochemistry of the aminodiols.
• Franklin et al., Journal of the Chemical Society, 1954, p. 1683,1685
  作者：Franklin et al.

  DOI：——

  日期：——