(2R,3R)-2-Methyl-6-[10-(2-methyl-[1,3]dioxolan-2-yl)-decyl]-2,3,4,5-tetrahydro-pyridin-3-ol | 187745-57-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-2-Methyl-6-[10-(2-methyl-[1,3]dioxolan-2-yl)-decyl]-2,3,4,5-tetrahydro-pyridin-3-ol
• 英文别名: (2R,3R)-2-methyl-6-[10-(2-methyl-1,3-dioxolan-2-yl)decyl]-2,3,4,5-tetrahydropyridin-3-ol
• CAS: 187745-57-9
• 化学式: C₂₀H₃₇NO₃
• 分子量: 339.519
• InChiKey: BDEUKWIJIHGNSS-IEBWSBKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-Methyl-6-[10-(2-methyl-[1,3]dioxolan-2-yl)-decyl]-2,3,4,5-tetrahydro-pyridin-3-ol 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.75h， 生成 12-[(2S,5R,6R)-5-羟基-6-甲基-2-哌啶基]-2-十二烷酮
  参考文献：
  名称：

  Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine

  摘要：

  A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral beta-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00537-x
• 作为产物：
  描述：

  (4R,5R)-5-(3-Hydroxy-propyl)-4-methyl-oxazolidin-2-one 在 六甲基磷酰三胺 、 barium dihydroxide 、 jones reagent 、 magnesium 、 1,2-二溴乙烷 、 N,N'-羰基二咪唑 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 26.5h， 生成 (2R,3R)-2-Methyl-6-[10-(2-methyl-[1,3]dioxolan-2-yl)-decyl]-2,3,4,5-tetrahydro-pyridin-3-ol
  参考文献：
  名称：

  Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine

  摘要：

  A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral beta-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00537-x

文献信息

• Total synthesis of the piperidinol alkaloid (−)-(2R,3R,6S)-cassine
  作者：Jörg Oetting、Jens Holzkamp、Hartmut H. Meyer、Axel Pahl

  DOI：10.1016/s0957-4166(96)00537-x

  日期：1997.2

  A highly efficient, flexible and diastereoselective route to all-cis-2,6-disubstituted 3-piperidinols has been accomplished. The key component of the synthesis is a chiral beta-hydroxyester, which was obtained by lipase catalyzed kinetic resolution. Based on this starting material, diastereoselective alkylation of its dianion, Curtius rearrangement to a 2-oxazolidinone, Grignard reaction to introduce the side-chain and conversion of the aliphatic 2-oxazolidinone into a 3-piperidinol by imine cyclization lead to the exemplary total synthesis of naturally occurring (-)-(2R,3R,6S)-cassine. (C) 1997 Elsevier Science Ltd. All rights reserved.