[(4S)-9-phenylmethoxynon-5-yn-4-yl] pyridine-2-carboxylate | 1258153-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [(4S)-9-phenylmethoxynon-5-yn-4-yl] pyridine-2-carboxylate
• CAS: 1258153-67-1
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: AUAWDCXDCLAAGE-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4S)-9-phenylmethoxynon-5-yn-4-yl] pyridine-2-carboxylate 在 氢气 作用下， 以92%的产率得到(S,Z)-9-(benzyloxy)non-5-en-4-yl picolinate
  参考文献：
  名称：

  Synthesis of ACAT inhibitors through substitution using allylic picolinate and copper reagent

  摘要：

  Amide of an octanoic acid possessing an aryl group at C3 position is a highly potent ACAT inhibitor. In this paper, we describe a synthetic access to this class of compounds as optically active forms. The key reaction is substitution of the allylic picolinate of (S,Z)-8-(benzyloxy)oct-5-en-4-ol with a copper reagent derived from (benzo[d][1,3]dioxol-4-yl)MgBr and CuBr center dot Me(2)S to produce anti S(N)2' product regio- and stereo-selectively. The product was hydrogenated to afford (S)-3-benzo[d][1,3]dioxol-4-yloctan-1-ol, which upon oxidation furnished the octanoic acid. Finally, the acid was converted with 2,6-(i-Pr)(2) C(6)H(3)NH(2) to the target amide via acid chloride. In a similar way, the one-carbon long homolog was synthesized. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.035
• 作为产物：
  描述：

  2-吡啶甲酸 、 (4S)-9-phenylmethoxynon-5-yn-4-ol 在 4-二甲氨基吡啶 、 三乙胺 、 2-chloropyridinium iodide 作用下， 以95%的产率得到[(4S)-9-phenylmethoxynon-5-yn-4-yl] pyridine-2-carboxylate
  参考文献：
  名称：

  Synthesis of ACAT inhibitors through substitution using allylic picolinate and copper reagent

  摘要：

  Amide of an octanoic acid possessing an aryl group at C3 position is a highly potent ACAT inhibitor. In this paper, we describe a synthetic access to this class of compounds as optically active forms. The key reaction is substitution of the allylic picolinate of (S,Z)-8-(benzyloxy)oct-5-en-4-ol with a copper reagent derived from (benzo[d][1,3]dioxol-4-yl)MgBr and CuBr center dot Me(2)S to produce anti S(N)2' product regio- and stereo-selectively. The product was hydrogenated to afford (S)-3-benzo[d][1,3]dioxol-4-yloctan-1-ol, which upon oxidation furnished the octanoic acid. Finally, the acid was converted with 2,6-(i-Pr)(2) C(6)H(3)NH(2) to the target amide via acid chloride. In a similar way, the one-carbon long homolog was synthesized. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.09.035

文献信息

• Synthesis of ACAT inhibitors through substitution using allylic picolinate and copper reagent
  作者：Yuichi Kobayashi、Paveena Lalitnorasate、Yuki Kaneko、Yohei Kiyotsuka、Yoshiki Endo

  DOI：10.1016/j.tetlet.2010.09.035

  日期：2010.11

  Amide of an octanoic acid possessing an aryl group at C3 position is a highly potent ACAT inhibitor. In this paper, we describe a synthetic access to this class of compounds as optically active forms. The key reaction is substitution of the allylic picolinate of (S,Z)-8-(benzyloxy)oct-5-en-4-ol with a copper reagent derived from (benzo[d][1,3]dioxol-4-yl)MgBr and CuBr center dot Me(2)S to produce anti S(N)2' product regio- and stereo-selectively. The product was hydrogenated to afford (S)-3-benzo[d][1,3]dioxol-4-yloctan-1-ol, which upon oxidation furnished the octanoic acid. Finally, the acid was converted with 2,6-(i-Pr)(2) C(6)H(3)NH(2) to the target amide via acid chloride. In a similar way, the one-carbon long homolog was synthesized. (C) 2010 Elsevier Ltd. All rights reserved.