methyl (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-9H-pyrido[3,4-b]indole-3-carboxylate | 1443051-69-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: methyl (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-9H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: methyl 1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1443051-69-1
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: JBKPDRPOJBDTNT-AWEZNQCLSA-N

物化性质

• 沸点：
  549.7±50.0 °C(Predicted)
• 密度：
  1.299±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-9H-pyrido[3,4-b]indole-3-carboxylate 在 盐酸 、 二异丁基氢化铝 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 8.33h， 生成 15,16-O-diacetylpyridindolol
  参考文献：
  名称：

  Novel asymmetric total syntheses of (R)-(−)-pyridindolol, (R)-(−)-pyridindolol K1, and (R)-(−)-pyridindolol K2 via a mild one-pot aromatization of N-tosyl-tetrahydro-β-carboline with (S)-2,3-O-isopropylidene-l-glyceraldehyde as the source of chirality

  摘要：

  Novel total syntheses of (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 are described. By using L-tryptophan methyl ester and (S)-2,3-O-isopropylidene-L-glyceraldehyde as the starting materials, (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 were synthesized in 5-7 steps in 66%, 41%, and 55% overall yields, respectively. The characteristic step of the total syntheses is a mild one-pot aromatization of N-tosyl-1,2,3,4-tetrahydro-beta-carboline (N-Ts-THBC), which was obtained via Pictet-Spengler reaction of L-tryptophan methyl ester with (S)-2,3-O-isopropylidene-L-glyceraldehyde, and subsequent N-tosylation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.009
• 作为产物：
  描述：

  methyl (3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-tosyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 以87%的产率得到methyl (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-9H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  Novel asymmetric total syntheses of (R)-(−)-pyridindolol, (R)-(−)-pyridindolol K1, and (R)-(−)-pyridindolol K2 via a mild one-pot aromatization of N-tosyl-tetrahydro-β-carboline with (S)-2,3-O-isopropylidene-l-glyceraldehyde as the source of chirality

  摘要：

  Novel total syntheses of (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 are described. By using L-tryptophan methyl ester and (S)-2,3-O-isopropylidene-L-glyceraldehyde as the starting materials, (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 were synthesized in 5-7 steps in 66%, 41%, and 55% overall yields, respectively. The characteristic step of the total syntheses is a mild one-pot aromatization of N-tosyl-1,2,3,4-tetrahydro-beta-carboline (N-Ts-THBC), which was obtained via Pictet-Spengler reaction of L-tryptophan methyl ester with (S)-2,3-O-isopropylidene-L-glyceraldehyde, and subsequent N-tosylation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.009

文献信息

• Novel asymmetric total syntheses of (R)-(−)-pyridindolol, (R)-(−)-pyridindolol K1, and (R)-(−)-pyridindolol K2 via a mild one-pot aromatization of N-tosyl-tetrahydro-β-carboline with (S)-2,3-O-isopropylidene-l-glyceraldehyde as the source of chirality
  作者：Qiang Zhang、Zhen Fan、Jing Dong、Xiao-Xin Shi、Xia Lu

  DOI：10.1016/j.tetasy.2013.04.009

  日期：2013.6

  Novel total syntheses of (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 are described. By using L-tryptophan methyl ester and (S)-2,3-O-isopropylidene-L-glyceraldehyde as the starting materials, (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 were synthesized in 5-7 steps in 66%, 41%, and 55% overall yields, respectively. The characteristic step of the total syntheses is a mild one-pot aromatization of N-tosyl-1,2,3,4-tetrahydro-beta-carboline (N-Ts-THBC), which was obtained via Pictet-Spengler reaction of L-tryptophan methyl ester with (S)-2,3-O-isopropylidene-L-glyceraldehyde, and subsequent N-tosylation. (C) 2013 Elsevier Ltd. All rights reserved.