(3R,4R)-3-ethanoyloxy-4-n-propyl-cyclopentanone | 386272-79-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3R,4R)-3-ethanoyloxy-4-n-propyl-cyclopentanone
• 英文别名: (3R,4R)-3-acetoxy-4-n-propyl-cyclopentanone；[(1R,2R)-4-oxo-2-propylcyclopentyl] acetate
• CAS: 386272-79-3
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: TWDNJRPKJRNOSL-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-ethanoyloxy-4-n-propyl-cyclopentanone 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 为溶剂， 生成 C₈H₁₂O
  参考文献：
  名称：

  Synthesis and in vivo evaluation of 3-substituted gababutins

  摘要：

  A range of 3-alkylated five-membered ring derivatives of Gabapentin were synthesized and several were found to have good levels of potency against the alpha 2 delta calcium subunit of a voltage-gated calcium channel. Two compounds were pro. led in in vivo models of pain and anxiety. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.089
• 作为产物：
  描述：

  (1r)-4-氧代环戊-2-烯-1-基乙酸酯 、 丙基氯化镁 在 Dimethylzinc 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4R)-3-ethanoyloxy-4-n-propyl-cyclopentanone
  参考文献：
  名称：

  Synthesis and in vivo evaluation of 3-substituted gababutins

  摘要：

  A range of 3-alkylated five-membered ring derivatives of Gabapentin were synthesized and several were found to have good levels of potency against the alpha 2 delta calcium subunit of a voltage-gated calcium channel. Two compounds were pro. led in in vivo models of pain and anxiety. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.089

文献信息

• Cyclic ketones, their preparation and their use in the synthesis of amino acids
  申请人：——

  公开号：US20030187296A1

  公开（公告）日：2003-10-02

  A method is provided for making an enantiomerically pure of the formula: in which R and R′ represent C1?C10 alkyl, C2?C10 alkenyl or C3?C10 cycloalkyl and the wedges signify (S)- or (R)-stereochemistry, the substituents in compound (II) being trans. Conjugate addition is carried out between an organometallic nucleophile that provides a group R as defined above and (R)-4-acetoxycyclopent-2-en-1-one, (S)-4-acetoxycyclopent-2-en-1-one or a similar compound in which acetoxy is replaced by another leaving group to give, e.g. in the case of the acetoxy compound, a trans 3,4-disubstituted addition product of formula III or IV; The acetyl group is eliminated from the addition product to give an (R)- or (S)-4-alkyl or 4-alkenyl cyclopent-2-en-1-one the compound of formula is then to be hydrogenated to give a cyclopentanone of formula (I) or conjugate addition of a second organometallic nucleophile that provides a group R′ as defined above to the compound of the above formula may be carried out to give a trans 3,4-disubstituted addition product of formula (II). One of the above compounds may be converted e.g. via an intermediate (XV)-(XVIII) (in which the substituents R and R′ and the wedges have the meanings indicated above) to a gabapentin analogue of one of the formulae shown below: in which the substituents R and R′ and the wedges also have the meanings indicated above. 1 2

  提供一种制备公式的对映纯物质的方法：其中R和R′代表C1-C10烷基、C2-C10烯基或C3-C10环烷基，楔形符号表示(S)-或(R)-立体化学，化合物(II)中的取代基为反式。在有机金属亲核试剂和(R)-4-乙酰氧基环戊-2-烯-1-酮、(S)-4-乙酰氧基环戊-2-烯-1-酮或类似化合物之间进行共轭加成，其中乙酰氧基被另一个离去基取代，例如在乙酰氧基化合物的情况下，得到公式III或IV的反式3,4-二取代加成产物；从加成产物中消除乙酰基，得到(R)-或(S)-4-烷基或4-烯基环戊-2-烯-1-酮，然后将该化合物氢化，得到公式(I)的环戊酮，或者对上述公式的化合物进行第二次有机金属亲核试剂的共轭加成，得到公式(II)的反式3,4-二取代加成产物。上述化合物之一可以通过中间体(XV)-(XVIII)（其中取代基R和R′以及楔形符号具有上述所示的含义）转化为下面所示的公式之一的加巴喷丁类似物：其中取代基R和R′以及楔形符号也具有上述所示的含义。
• US6872856B2
  申请人：——

  公开号：US6872856B2

  公开（公告）日：2005-03-29