(S)-3-benzo[d][1,3]dioxol-4-yloctan-1-ol | 1258153-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (S)-3-benzo[d][1,3]dioxol-4-yloctan-1-ol
• CAS: 1258153-64-8
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: KVSPZPYMNUJSMT-LBPRGKRZSA-N

反应信息

• 作为反应物：
  描述：

  (S)-3-benzo[d][1,3]dioxol-4-yloctan-1-ol 在 chromium(VI) oxide 作用下， 以92%的产率得到(S)-3-(2, 3-methylenedioxyphenyl)octanoic acid
  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：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以26 mg的产率得到(S)-3-benzo[d][1,3]dioxol-4-yloctan-1-ol
  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