ethyl 3-azido-2-hydroxy-3-(4-methoxyphenyl)propanoate | 780795-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 3-azido-2-hydroxy-3-(4-methoxyphenyl)propanoate
• CAS: 780795-84-8
• 化学式: C₁₂H₁₅N₃O₄
• 分子量: 265.269
• InChiKey: JYGZGNAXUKKTSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-azido-2-hydroxy-3-(4-methoxyphenyl)propanoate 在 palladium on activated charcoal 氢气 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、70.93 kPa 条件下， 反应 16.0h， 生成 (4R,5S)-4-(4-Methoxy-phenyl)-2-oxo-oxazolidine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Madhusudhan; Om Reddy; Ramanatham, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 12, p. 2683 - 2688

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(4-甲氧基苯基)-环氧乙烷羧酸乙酯 在 sodium azide 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 生成 ethyl 3-azido-2-hydroxy-3-(4-methoxyphenyl)propanoate
  参考文献：
  名称：

  Madhusudhan; Reddy, M. Srinivasa; Reddy, Y. Narayana, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 7, p. 978 - 984

  摘要：

  DOI：

文献信息

• Highly regioselective ring opening of epoxides using NaN3: a short and efficient synthesis of (−)-cytoxazone
  作者：Joshodeep Boruwa、Jagat C. Borah、Biswajit Kalita、Nabin C. Barua

  DOI：10.1016/j.tetlet.2004.07.157

  日期：2004.9

  A convenient and efficient synthesis of 1,2-azido alcohols has been achieved by regioselective ring opening of epoxides using NaN3 and 4 Å molecular sieves in acetonitrile. The utility of this method has been demonstrated by achieving a short synthesis of (−)-cytoxazone in 48% overall yield.

  通过使用乙腈中的NaN 3和4Å分子筛对环氧化物进行区域选择性开环，已实现了一种便捷高效的1,2叠氮基醇的合成。通过以48％的总收率实现（-）-cytoxazone的短时合成，已证明了该方法的实用性。
• Unusual Regioselection in the Mitsunobu Reactions of <i>s</i><i>yn</i>-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer
  作者：Soo Y. Ko

  DOI：10.1021/jo015967f

  日期：2002.4.1

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.
• Madhusudhan; Ravibabu; Narendar Reddy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 1, p. 96 - 101
  作者：Madhusudhan、Ravibabu、Narendar Reddy、Gurunadham、Dubey

  DOI：——

  日期：——