(S)-4-acetoxy-2-cyclopentenone | 59995-50-5

• 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: (S)-4-acetoxy-2-cyclopentenone
• 英文别名: (S)-4-oxocyclopenten-2-yl acetate；(S)-4-acetoxy-2-cyclopenten-1-one；(S)-4-Acetoxycyclopent-2-en-1-one；(S)-4-acetoxycyclopent-2-enone；(S)-4-oxocyclopent-2-en-1-yl acetate；(S)-4-oxocyclopent-2-enyl acetate；(S)-4-Acetoxy-2-cyclopentenon；(4S)-4-Acetoxy-2-cyclopenten-1-one；[(1S)-4-oxocyclopent-2-en-1-yl] acetate
• CAS: 59995-50-5
• 化学式: C₇H₈O₃
• 分子量: 140.139
• InChiKey: YNCKAQVPQJWLJW-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  (S)-4-acetoxy-2-cyclopentenone 生成 (R)-4-[(E)-(S)-4-(tert-Butyl-dimethyl-silanyloxy)-non-1-enyl]-cyclopent-2-enone
  参考文献：
  名称：

  MANDAI, TADAKATSU;MATSUMOTO, SHIN-ICHI;KOHAMA, MAKOTO;KAWADA, MIKIO;TSUJI+, J. ORG. CHEM., 55,(1990) N2, C. 5671-5673

  摘要：

  DOI：
• 作为产物：
  描述：

  (4R)-(+)-T-丁基二甲基硅氧-1-酮 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (S)-4-acetoxy-2-cyclopentenone
  参考文献：
  名称：

  顺式-4-叔丁基二甲基甲硅烷氧基-2-环戊烯-1-醇和顺式-4-四氢吡喃氧基-2-环戊烯-1-醇的不对称合成

  摘要：

  通过顺式-3,4-环氧环戊烷-的反应，以高对映体过量（ee）获得顺式-4-叔丁基二甲基甲硅烷氧基-2-环戊烯-1-醇和顺式-4-四氢吡喃氧基-2-环戊烯-1-醇。具有手性锂酰胺的1-ol衍生物。证明了在（S）-和（R）-4-羟基-2-环戊烯酮的合成中的应用。

  DOI：

  10.1016/s0040-4039(00)98931-7

文献信息

• 4-Heterosubstituted Cyclopentenone Antiviral Compounds: Synthesis, Mechanism, and Antiviral Evaluation
  作者：Daniele Mantione、Olatz Olaizola Aizpuru、Misal Giuseppe Memeo、Bruna Bovio、Paolo Quadrelli

  DOI：10.1002/ejoc.201501406

  日期：2016.2

  in a short synthesis of nucleoside analogues with pyrimidine and purine heterobases. The protocol is based on a typical nucleophilic substitution process. Uracil, thymine, 6-chloropurine, and some adenines gave the expected 4-heterosubstituted products along with the isomeric 2-heterosubstituted compounds as minor components. Samples of selected products were evaluated for their antiviral activity in

  外消旋的 4-oxocyclopent-2-en-1-yl 乙酸盐用于短时间合成带有嘧啶和嘌呤杂碱基的核苷类似物。该协议基于典型的亲核取代过程。尿嘧啶、胸腺嘧啶、6-氯嘌呤和一些腺嘌呤产生预期的 4-杂取代产物以及作为次要组分的异构 2-杂取代化合物。在针对属于不同类别的各种病毒的初步筛选中，对选定产品的样品的抗病毒活性进行了评估。发现其中一种化合物对人乳头瘤病毒 (HPV) 具有高度活性。
• 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。
• A Novel Asymmetric Synthesis of Chiral Cyclopentanoid Building Blocks by the Use of Chiral Lithium Amide
  作者：Masatoshi Asami

  DOI：10.1246/bcsj.63.1402

  日期：1990.5

  Enantioselective deprotonation of meso-epoxides, derived from 3-cyclopenten-1-ol, was examined using chiral lithium amide. Chiral cis-4-t-butyldimethylsiloxy-2-cyclopenten-1-ol, cis-4-tetrahydropyranyloxy-2-cyclopenten-1-ol, and their trans-isomers, which are useful chiral building blocks for the synthesis of cyclopentanoid natural compounds, were obtained with high enantiomeric excesses (72–90% ee)

  使用手性氨基化锂检查衍生自 3-环戊烯-1-醇的内消旋环氧化物的对映选择性去质子化。手性 cis-4-t-丁基二甲基甲硅烷氧基-2-cyclopenten-1-ol、cis-4-tetrahydropyranyloxy-2-cyclopenten-1-ol 及其反式异构体，它们是合成环戊烷类天然化合物的有用手性构件, 以高对映体过量 (72-90% ee) 获得。(R)- 和 (S)-4-hydroxy-2-cyclopenten-1-one 均立体定向地衍生自 (1S,4R)-4-t-丁基二甲基甲硅烷氧基-2-cyclopenten-1-ol。
• Enantioselective Synthesis of 4-Heterosubstituted Cyclopentenones
  作者：Kathrin Ulbrich、Peter Kreitmeier、Tirayut Vilaivan、Oliver Reiser

  DOI：10.1021/jo400409f

  日期：2013.4.19

  Racemic 4-hydroxycyclopentenone, readily derived from furfuryl alcohol, can be transformed via its O-Boc derivative to 4-acyloxy, 4-aryloxy-, 4-amino-, or 4-thio-substituted cyclopentenones with high enantioselectivity by palladium-catalyzed kinetic resolution via nucleophilic allylic substitutions. Applying this methodology, a short formal synthesis of ent-noraristeromycin was readily accomplished

  易于衍生自糠醇的外消旋4-羟基环戊烯酮可通过其O -Boc衍生物通过钯催化的动力学以高对映体选择性转化为4-酰氧基，4-芳氧基-，4-氨基-或4-硫基取代的环戊烯亲核烯丙基取代解决。应用这种方法，短正式合成耳鼻喉科-noraristeromycin容易地完成。
• Synthesis and in vivo evaluation of 3,4-disubstituted gababutins
  作者：David C. Blakemore、Justin S. Bryans、Pauline Carnell、Mark J. Field、Natasha Kinsella、Jack K. Kinsora、Leonard T. Meltzer、Simon A. Osborne、Lisa R. Thompson、Sophie C. Williams

  DOI：10.1016/j.bmcl.2009.10.121

  日期：2010.1

  A range of 3,4-alkylated five-membered ring derivatives of gabapentin were synthesised. One compound (21) had an excellent level of potency against alpha(2)delta and was pro. led in in vivo models of pain and anxiety. (c) 2009 Elsevier Ltd. All rights reserved.