(S)-N-(1-indolyl)acetyl-4-benzyl-2-oxazolidinone | 438620-32-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-N-(1-indolyl)acetyl-4-benzyl-2-oxazolidinone
• 英文别名: (4S)-4-benzyl-3-(2-indol-1-ylacetyl)-1,3-oxazolidin-2-one
• CAS: 438620-32-7
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: MKOBOIYVGBZEBY-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-indolyl)acetyl-4-benzyl-2-oxazolidinone 在 盐酸 、 lithium hydroxide 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.75h， 生成 (S)-4-苄基-2-唑烷酮
  参考文献：
  名称：

  Addition of chiral enolates to N-alkyl-3-acylpyridinium salts. Total synthesis of (+)-16-epivinoxine and (−)-vinoxine

  摘要：

  Chiral enolates of indolylacetyl derivatives 6a-f undergo addition to pyridinium salt 7 with complete trans-selectivity and varied diastereofacial selectivities to give, after acid-induced cyclization of the intermediate 1,4-dihydropyridines, the vinoxine-related tetracycles 8a-f. Starting from (S)-prolinol indolylacetamide 6e, subsequent elaboration of the ethylidene substituent from tetracycle 8e and removal of the chiral auxiliary has resulted in a straightforward synthesis of (+)-16-epivinoxine and (-)-vinoxine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00055-1
• 作为产物：
  描述：

  吲哚-1-乙酸 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (S)-N-(1-indolyl)acetyl-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  Addition of chiral enolates to N-alkyl-3-acylpyridinium salts. Total synthesis of (+)-16-epivinoxine and (−)-vinoxine

  摘要：

  Chiral enolates of indolylacetyl derivatives 6a-f undergo addition to pyridinium salt 7 with complete trans-selectivity and varied diastereofacial selectivities to give, after acid-induced cyclization of the intermediate 1,4-dihydropyridines, the vinoxine-related tetracycles 8a-f. Starting from (S)-prolinol indolylacetamide 6e, subsequent elaboration of the ethylidene substituent from tetracycle 8e and removal of the chiral auxiliary has resulted in a straightforward synthesis of (+)-16-epivinoxine and (-)-vinoxine. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00055-1

文献信息

• Addition of chiral enolates to N-alkyl-3-acylpyridinium salts. Total synthesis of (+)-16-epivinoxine and (−)-vinoxine
  作者：M.-Lluı̈sa Bennasar、Ester Zulaica、Yolanda Alonso、Bernat Vidal、Jesús T. Vázquez、Joan Bosch

  DOI：10.1016/s0957-4166(02)00055-1

  日期：2002.2

  Chiral enolates of indolylacetyl derivatives 6a-f undergo addition to pyridinium salt 7 with complete trans-selectivity and varied diastereofacial selectivities to give, after acid-induced cyclization of the intermediate 1,4-dihydropyridines, the vinoxine-related tetracycles 8a-f. Starting from (S)-prolinol indolylacetamide 6e, subsequent elaboration of the ethylidene substituent from tetracycle 8e and removal of the chiral auxiliary has resulted in a straightforward synthesis of (+)-16-epivinoxine and (-)-vinoxine. (C) 2002 Elsevier Science Ltd. All rights reserved.