5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione | 67996-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-[(2,5-dimethoxyphenyl)-(indol-3-yl)-methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[(2,5-dimethoxy-phenyl)-indol-3-yl-methyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione；5-[(2,5-dimethoxyphenyl)-(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 67996-13-8
• 化学式: C₂₃H₂₃NO₆
• 分子量: 409.439
• InChiKey: XTAZLGUKLZDOBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione 在 palladium on activated charcoal 二苯基磷酸 、 氢气 、 三乙胺 作用下， 以 吡啶 、 乙醇 、 溶剂黄146 、 甲苯 为溶剂， 反应 10.5h， 生成 cis-(3S*,4S*)-4-(2,5-dimethoxyphenyl)-1,2,3,4-tetrahydrospiro[β-carboline-1,1'-cyclohexane]-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A Convenient Synthesis of Conformationally Constrained β-Substituted Tryptophans

  摘要：

  A short and general synthesis for the preparation of various conformationally constrained beta-substituted tryptophans has been elaborated starting from indole, aldehydes and Meldrum's acid by using trimolecular condensation and Curtius rearrangement mediated functional group transformations followed by deprotections, as key-steps. The relative configurations of the two diastereomeric series have been determined indirectly by the measurement of (3)J coupling constants in the corresponding tetrahydro-beta-carbolines, and further supported by means of molecular modelizations. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00446-4
• 作为产物：
  描述：

  吲哚 、 丙二酸环(亚)异丙酯 、 2,5-二甲氧基苯甲醛 在 L-脯氨酸 作用下， 以 乙腈 为溶剂， 反应 28.0h， 以88%的产率得到5-<(2,5-dimethoxyphenyl)-1H-indol-3-ylmethyl>-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Oikawa, Yuji; Hirasawa, Hitoshi; Yonemitsu, Osamu, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 9, p. 3092 - 3096

  摘要：

  DOI：

文献信息

• Oikawa, Yuji; Hirasawa, Hitoshi; Yonemitsu, Osamu, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 9, p. 3092 - 3096
  作者：Oikawa, Yuji、Hirasawa, Hitoshi、Yonemitsu, Osamu

  DOI：——

  日期：——
• Meldrum's acid in organic synthesis. 1. A convenient one-pot synthesis of ethyl indolepropionates
  作者：Yuji Oikawa、Hitoshi Hirasawa、Osamu Yonemitsu

  DOI：10.1016/0040-4039(78)80037-9

  日期：1978.1
• OIKAWA, YUJI;HIRASAWA, HIROSHI;YONEMITSU, OSAMU, CHEM. AND PHARM. BULL., 1982, 30, N 9, 3092-3096
  作者：OIKAWA, YUJI、HIRASAWA, HIROSHI、YONEMITSU, OSAMU

  DOI：——

  日期：——
• A Convenient Synthesis of Conformationally Constrained β-Substituted Tryptophans
  作者：Csaba Nemes、Laurent Jeannin、Janos Sapi、Marie Laronze、Houria Seghir、Franck Augé、Jean-Yves Laronze

  DOI：10.1016/s0040-4020(00)00446-4

  日期：2000.7

  A short and general synthesis for the preparation of various conformationally constrained beta-substituted tryptophans has been elaborated starting from indole, aldehydes and Meldrum's acid by using trimolecular condensation and Curtius rearrangement mediated functional group transformations followed by deprotections, as key-steps. The relative configurations of the two diastereomeric series have been determined indirectly by the measurement of (3)J coupling constants in the corresponding tetrahydro-beta-carbolines, and further supported by means of molecular modelizations. (C) 2000 Elsevier Science Ltd. All rights reserved.