2,2,2-trichloroethyl (2α,3α,6α)-3-hydroxy-2-methyl-6-(12-oxododecyl)-2-methyl-1-piperidinecarboxylate

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 2,2,2-trichloroethyl (2α,3α,6α)-3-hydroxy-2-methyl-6-(12-oxododecyl)-2-methyl-1-piperidinecarboxylate
• 英文别名: 2,2,2-trichloroethyl (2S,3S,6R)-3-hydroxy-2-methyl-6-(12-oxododecyl)piperidine-1-carboxylate
• 化学式: C₂₁H₃₆Cl₃NO₄
• 分子量: 472.88
• InChiKey: MJZDRBVXSHNKBV-OTWHNJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,2-trichloroethyl (2α,3α,6α)-3-hydroxy-2-methyl-6-(12-oxododecyl)-2-methyl-1-piperidinecarboxylate 在 氢氧化钾 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 、 水 、 异丙醇 为溶剂， 反应 72.5h， 生成 (2α,3α,6α)-6,6'-[(1,2,3,5,8,8a-hexahydro-6,8-indolizinediyl)di-10,1-decanediyl]-bis[2-methyl-3-piperidinol]
  参考文献：
  名称：

  Syntheses of Ficuseptine, Juliprosine, and Juliprosopine by Biomimetic Intramolecular Chichibabin Pyridine Syntheses

  摘要：

  Biomimetic intramolecular Chichibabin pyridine syntheses using two molecules of an aldehyde and 4-aminobutanal dimethyl acetal (6) proceed efficiently in AcOH at 95 degrees C to give 2,3-dihydro-1H-indolizinium salts. Reaction occurs at 25 degrees C if 1-pyrroline (5) is used instead of 6. This reaction has been used for a one-step synthesis of ficuseptine (1) and the first syntheses of juliprosine (2) and juliprosopine (17t), which is now assigned as the trans stereoisomer.

  DOI：

  10.1021/ol050931l
• 作为产物：
  描述：

  6-溴-3-羟基-2-甲基吡啶 在 Rh/Al₂O₃ 吡啶 、 甲醇 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 硫酸 、 氢气 、 magnesium 、 N,N-二异丙基乙胺 、 potassium bromide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 25.0~65.0 ℃ 、344.74 kPa 条件下， 反应 96.0h， 生成 2,2,2-trichloroethyl (2α,3α,6α)-3-hydroxy-2-methyl-6-(12-oxododecyl)-2-methyl-1-piperidinecarboxylate
  参考文献：
  名称：

  Syntheses of Ficuseptine, Juliprosine, and Juliprosopine by Biomimetic Intramolecular Chichibabin Pyridine Syntheses

  摘要：

  Biomimetic intramolecular Chichibabin pyridine syntheses using two molecules of an aldehyde and 4-aminobutanal dimethyl acetal (6) proceed efficiently in AcOH at 95 degrees C to give 2,3-dihydro-1H-indolizinium salts. Reaction occurs at 25 degrees C if 1-pyrroline (5) is used instead of 6. This reaction has been used for a one-step synthesis of ficuseptine (1) and the first syntheses of juliprosine (2) and juliprosopine (17t), which is now assigned as the trans stereoisomer.

  DOI：

  10.1021/ol050931l

文献信息

• Syntheses of Ficuseptine, Juliprosine, and Juliprosopine by Biomimetic Intramolecular Chichibabin Pyridine Syntheses
  作者：Barry B. Snider、Bobbianna J. Neubert

  DOI：10.1021/ol050931l

  日期：2005.6.1

  Biomimetic intramolecular Chichibabin pyridine syntheses using two molecules of an aldehyde and 4-aminobutanal dimethyl acetal (6) proceed efficiently in AcOH at 95 degrees C to give 2,3-dihydro-1H-indolizinium salts. Reaction occurs at 25 degrees C if 1-pyrroline (5) is used instead of 6. This reaction has been used for a one-step synthesis of ficuseptine (1) and the first syntheses of juliprosine (2) and juliprosopine (17t), which is now assigned as the trans stereoisomer.