(1R,3R,4S)-menthyl 1-indoleacetate | 438620-29-2

• 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,3R,4S)-menthyl 1-indoleacetate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-indol-1-ylacetate
• CAS: 438620-29-2
• 化学式: C₂₀H₂₇NO₂
• 分子量: 313.44
• InChiKey: SYNDCDVVEBNNLM-HHXXYDBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3R,4S)-menthyl 1-indoleacetate 在 盐酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.25h， 生成 (1R,3R,4S)-menthyl (1R*,2S*,6S*)-5-(2-acetoxyethyl)-3-[(E)-2-(methoxycarbonyl)vinyl]-1,2,5,6-tetrahydro-2,6-methano[1,4]diazocino[1,2-a]indole-1-carboxylate
  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 、 L-薄荷醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 144.0h， 以57%的产率得到(1R,3R,4S)-menthyl 1-indoleacetate
  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.