2-acetoxycyclopentanone | 52789-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetoxycyclopentanone
• 英文别名: 2-oxocyclopentyl acetate；Cyclopentanone, 2-(acetyloxy)-；(2-oxocyclopentyl) acetate
• CAS: 52789-75-0
• 化学式: C₇H₁₀O₃
• mdl: MFCD19300901
• 分子量: 142.155
• InChiKey: RBEIPUMJEQUKIW-UHFFFAOYSA-N

物化性质

• 沸点：
  115-117 °C(Press: 12 Torr)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 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：

  2-acetoxycyclopentanone 190.0 ℃ 、1.6 kPa 条件下， 生成 2-环戊烯酮
  参考文献：
  名称：

  Wanzlick et al., Chemische Berichte, 1955, vol. 88, p. 69,73

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-1,2-cyclopentanediol 在 吡啶 、 草酰氯 、 Amano PS Lipase 、 二甲基亚砜 作用下， 以 二氯甲烷 、 水 、 Petroleum ether 、 苯 为溶剂， 反应 42.25h， 生成 2-acetoxycyclopentanone
  参考文献：
  名称：

  Enantioselective enzymatic approach to (+)- and (−)-2-acetoxy/hydroxycyclopentanones

  摘要：

  A new practical enzymatic approach to (+)- and (-)-2-acetoxy/hydroxycyclopentanones with 96-98% ee has been described via enzymatic hydrolysis of the meso-diacetate 2, Swern oxidation of the thus formed (+/-)-hydroxy acetates 3 and 4, followed by re-enzymatic resolution. Enantiomerically pure (+)- and (-)-2-hydroxycyclopentanones are in equilibrium with enediol 9 and slowly undergo racemisation, a process which could be arrested by protecting the hydroxyl group as the acetate. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00366-x

文献信息

• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2015180612A1

  公开（公告）日：2015-12-03

  Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.

  揭示了新型视黄醇相关孤儿受体γ（RORγ）调节剂及其在通过RORγ介导的疾病治疗中的应用。
• [EN] ALKYNYL ALCOHOLS AND METHODS OF USE<br/>[FR] ALCOOLS D'ALCYNYLE ET PROCÉDÉS D'UTILISATION CORRESPONDANTS
  申请人：HOFFMANN LA ROCHE

  公开号：WO2015025025A1

  公开（公告）日：2015-02-26

  The invention relates to compounds of Formula (0): wherein Q, A1-A8, R4 and R5 and each has the meaning as described herein. Compounds of Formula (0) and pharmaceutical compositions thereof are useful in the treatment of diseases and disorders in which undesired or over- activation of NF-kB signaling is observed.

  这项发明涉及以下式的化合物（0）：其中Q，A1-A8，R4和R5分别具有如本文所述的含义。式（0）的化合物及其药物组成物在治疗观察到NF-kB信号通路的不良或过度活化的疾病和紊乱中是有用的。
• Electroorganic Chemistry. XXVI. Electrooxidation of Enamines, Haloolefins, and Enol Ethers
  作者：Tatsuya Shono、Yoshihiro Matsumura、Hiroshi Hamaguchi、Tamotsu Imanishi、Kaoru Yoshida

  DOI：10.1246/bcsj.51.2179

  日期：1978.7

  Electrooxidation of enamines in methanol afforded two types of methoxylated enamines. Similar treatment of enol ethers gave trimethoxylated compounds. The products formed by the electrolysis of haloolefins in acetic acid were α-acetoxy haloolefins and α-acetoxy ketones.

  烯胺在甲醇中的电氧化得到两种类型的甲氧基化烯胺。烯醇醚的类似处理得到三甲氧基化合物。卤代烯烃在乙酸中电解生成的产物为α-乙酰氧基卤代烯烃和α-乙酰氧基酮。
• Method of Treating Pathological Blushing
  申请人：Tobert A. Jonathan

  公开号：US20070299122A1

  公开（公告）日：2007-12-27

  A method of treating pathological blushing is disclosed wherein the patient is administered a DP receptor antagonist. Compositions containing DP antagonists are also included.

  揭示了一种治疗病理性面红的方法，其中患者接受DP受体拮抗剂。还包括含有DP拮抗剂的组合物。
• 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。