3-(tert-butyloxycarbonylamino)-1-(3-chlorophenyl)-4-hydroxybutan-1-one | 1434254-05-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(tert-butyloxycarbonylamino)-1-(3-chlorophenyl)-4-hydroxybutan-1-one
• 英文别名: tert-butyl N-[(2R)-4-(3-chlorophenyl)-1-hydroxy-4-oxobutan-2-yl]carbamate
• CAS: 1434254-05-3
• 化学式: C₁₅H₂₀ClNO₄
• 分子量: 313.781
• InChiKey: NKLYWIJZYWKANS-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(tert-butyloxycarbonylamino)-1-(3-chlorophenyl)-4-hydroxybutan-1-one 在 盐酸 、 sodium tetrahydroborate 、 cerium(III) chloride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 N-((2R,4S)-4-(3-chlorophenyl)-1,4-dihydroxybutan-2-yl)dodecanamide
  参考文献：
  名称：

  Chelation controlled reduction of N-protected β-amino ketones toward the synthesis of HPA-12 and analogues

  摘要：

  Diastereoselective reduction of N-protected beta-amino ketones does not proceed effectively under the conditions used for chelation controlled reductions of N-alkyl beta-amino ketones. A thorough analysis of various conditions required for the stereoselective reduction of gamma-aryl-gamma-oxo-beta-amino alcohols is reported. The products of the syn-selective reduction are used for the preparation of a ceramide trafficking inhibitor HPA-12 and analogues. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.04.016
• 作为产物：
  描述：

  tert-Butyl (S)-4-(iodomethyl)-2,2-dimethyloxazolidine-3-carboxylate 在 正丁基锂 、 水 、 碘 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成 3-(tert-butyloxycarbonylamino)-1-(3-chlorophenyl)-4-hydroxybutan-1-one
  参考文献：
  名称：

  Chelation controlled reduction of N-protected β-amino ketones toward the synthesis of HPA-12 and analogues

  摘要：

  Diastereoselective reduction of N-protected beta-amino ketones does not proceed effectively under the conditions used for chelation controlled reductions of N-alkyl beta-amino ketones. A thorough analysis of various conditions required for the stereoselective reduction of gamma-aryl-gamma-oxo-beta-amino alcohols is reported. The products of the syn-selective reduction are used for the preparation of a ceramide trafficking inhibitor HPA-12 and analogues. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.04.016

文献信息

• Synthesis of γ-Oxo γ-Aryl and γ-Aryl α-Amino Acids from Aromatic Aldehydes and Serine
  作者：Shibin Chacko、Ramesh Ramapanicker

  DOI：10.1002/ejoc.201201128

  日期：2012.12

  γ-Oxo α-amino acids and γ-aryl α-amino acids are compounds with very interesting biological properties and are active components of many drug molecules. Oxo amino acids are also used as synthetic precursors for a number of unnatural amino acids and amino alcohols. We report a very efficient synthesis of such compounds through the coupling of aromatic dithianes, prepared from aromatic aldehydes and an

  γ-氧代α-氨基酸和γ-芳基α-氨基酸是具有非常有趣的生物学特性的化合物，是许多药物分子的活性成分。含氧氨基酸还用作许多非天然氨基酸和氨基醇的合成前体。我们报告了通过芳族二噻烷的偶联非常有效地合成此类化合物，该芳族二噻烷由芳族醛和丝氨酸的碘化物衍生物制备。由此获得的化合物中的二噻烷基团可以水解或还原分别生成 4-氧代-4-芳基或 4-芳基 2-氨基丁醇衍生物，在进一步转化时，它们可以转化为标题化合物。从 L-丝氨酸开始提供具有完全对映纯度的相应 D-氨基酸。报告的方法在经济上可行并补充了现有方法，
• Chelation controlled reduction of N-protected β-amino ketones toward the synthesis of HPA-12 and analogues
  作者：Shibin Chacko、Mrinal Kalita、Ramesh Ramapanicker

  DOI：10.1016/j.tetasy.2015.04.016

  日期：2015.7

  Diastereoselective reduction of N-protected beta-amino ketones does not proceed effectively under the conditions used for chelation controlled reductions of N-alkyl beta-amino ketones. A thorough analysis of various conditions required for the stereoselective reduction of gamma-aryl-gamma-oxo-beta-amino alcohols is reported. The products of the syn-selective reduction are used for the preparation of a ceramide trafficking inhibitor HPA-12 and analogues. (C) 2015 Elsevier Ltd. All rights reserved.