(S)-ethyl 5-hydroxycyclopent-1-enecarboxylate | 143168-18-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (S)-ethyl 5-hydroxycyclopent-1-enecarboxylate
• 英文别名: ethyl (S)-5-hydroxycyclopent-1-enecarboxylate；(S)-2-carbethoxy-2-cyclopenten-1-ol；(S)-2-carbethoxy-2-cyclopent-1-ol；ethyl (5S)-5-hydroxycyclopentene-1-carboxylate
• CAS: 143168-18-7
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: ODFAUQJUEVMADD-ZETCQYMHSA-N

物化性质

• 沸点：
  247.9±40.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-ethyl 5-hydroxycyclopent-1-enecarboxylate 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 水 、 氢气 、 三正丁基氢锡 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 乙酸乙酯 、 乙腈 、 苯 为溶剂， 生成 ethyl 3-[(3aR,6aS)-2-hydroxy-2,3,4,5,6,6a-hexahydrocyclopenta[b]furan-3a-yl]propanoate
  参考文献：
  名称：

  Yamane, Takahiro; Ishizaki, Michiyo; Suzuki, Mahito, Heterocycles, 1996, vol. 42, # 1, p. 65 - 69

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基5-羟基-1-环戊烯-1-羧酸酯 在 乙酸乙烯酯 、 Pseudomonas sp. lipase 作用下， 以 甲基叔丁基醚 为溶剂， 反应 96.0h， 以50%的产率得到(S)-ethyl 5-hydroxycyclopent-1-enecarboxylate
  参考文献：
  名称：

  N-杂环卡宾催化α，β-不饱和烯醇酯重排合成（-）-7-Deoxyloganin

  摘要：

  α，β-不饱和烯醇酯（S）-2b的非对映选择性N-杂环卡宾（NHC）催化的重排已用于组装二氢吡喃酮（S）-3b，该材料体现了天然产品虹彩家族的双环核。通过化学选择性还原，然后进行立体选择性β-糖基化来精制该中间体，已经可以在随后的四个步骤中完成（-）-7-脱氧loganin（1）的总合成。

  DOI：

  10.1021/ol101983h

文献信息

• Synthesis and Duplex-Stabilizing Properties of Fluorinated<i>N</i>-Methanocarbathymidine Analogues Locked in the C3′-<i>endo</i>Conformation
  作者：Michael E. Jung、Timothy A. Dwight、Frederic Vigant、Michael E. Østergaard、Eric E. Swayze、Punit P. Seth

  DOI：10.1002/anie.201405283

  日期：2014.9.8

  The efficient synthesis, antiviral activity, and duplex‐stabilizing properties of both isomers of the 2′‐fluoro analogue of Northern methanocarbathymidine (N‐MCT), 2 and 3, are reported. We show that 2′‐F incorporation on the N‐MCT scaffold has a strong stabilizing effect on duplex thermal stability.

  报道了 Northern methanocarbathymidine (N-MCT) 的 2'-氟类似物的两种异构体2和3的有效合成、抗病毒活性和双链稳定特性。我们表明，在 N-MCT 支架上掺入 2'-F 对双链热稳定性具有很强的稳定作用。
• Concise formal synthesis of (−)-7-deoxyloganin via N-heterocyclic carbene catalysed rearrangement of α,β-unsaturated enol esters
  作者：Lisa Candish、David W. Lupton

  DOI：10.1039/c1ob05953j

  日期：——

  NHC catalysed rearrangement of α,β-unsaturated enol esters derived from formyl acetates and cyclopentyl annulated α,β-unsaturated acids provides the cyclopentapyranone core of (−)-7-deoxyloganin (1) with diastereo- and chemoselectivity in 6 steps starting from (−)-citronellal. The elaboration to the natural product has been investigated using two new approaches. The most successful intercepts our previous

  NHC催化从乙酸甲酰酯和环戊基环化的α，β-不饱和酸衍生的α，β-不饱和烯醇酯的重排为（-）-7-脱氧丹宁（1）的环戊吡喃酮核心提供了从6开始的非对映异构和化学选择性（-）-香茅醛。已使用两种新方法研究了对天然产物的精加工。最成功的方法是拦截我们先前在（-）-7-deoxyloganin（1）上的工作，从而允许完成10个步骤的正式总合成。
• Resolution and Utilization of Ethyl 5-Hydroxycyclopent-1-enecarboxylate: Enantioselective Synthesis of (+)-Mitsugashiwalactone and (-)-Dolichodial
  作者：Takahiro Yamane、Michiyasu Takahashi、Kunio Ogasawara

  DOI：10.1055/s-1995-3930

  日期：1995.4

  Optically pure ethyl 5-hydroxycyclopent-1-enecarboxylate has been obtained with its acetate in both enantiomeric forms in excellent optical yields from racemic ethyl 5-hydroxycyclopent-1-enecarboxylate by lipase-mediated kinetic resolution. The optically pure (R)-enantiomer thus obtained has been transformed into two naturally occurring iridoid monoterpenes, (+)-mitsugashiwalactone and (-)-dolichodial.

  光学纯的乙基5-羟基环戊-1-烯羧酸酯已通过脂肪酶介导的动力学分辨率，从外消旋乙基5-羟基环戊-1-烯羧酸酯中以优异的光学产率获得其醋酸酯的两种对映异构体。因此获得的光学纯（R）对映体已转化为两种天然存在的紫杉醇单萜，(+)-三叶紫杉醇内酯和(-)-多利克醛。
• Enantiocomplementary synthesis of functionalized cycloalkenol building blocks using lipase
  作者：Seiichi Takano、Takahiro Yamane、Michiyasu Takahashi、Kunio Ogasawara

  DOI：10.1016/s0957-4166(00)82178-3

  日期：1992.7

  Racemic 2-carbethoxy-2-cyclopenten-1-ol [(+/-)-3a] and racemic 2-carbethoxy-2-cyclohexen-1-ol [(+/-)-3b] afforded the corresponding (R)-acetates [(R)-4a and (R)-4b] leaving the corresponding (S)-alcohols [(S)-3a and (S)-3b] unchanged upon treatment with vinyl acetate in tert-butyl methyl ether in the presence of lipase PS, respectively, while the racemic acetates [(+/-)-4a and (+/-)-4b], derived from racemic precursors, (+/-)-3a and (+/-)-3b, on suspension with lipase in a phosphate buffer solution afforded the corresponding (R)-alcohols [(R)-3a and (R)-3b] leaving the corresponding (S)-acetates [(S)-4a and (S)-4b] unchanged, respectively.
• Candida antarctica lipase B-catalyzed reactions of β-hydroxy esters: Competition of acylation and hydrolysis
  作者：Enikő Forró、Zsolt Galla、Ferenc Fülöp

  DOI：10.1016/j.molcatb.2013.09.024

  日期：2013.12

  The ester function of ethyl cis-(+/-)-2-hydroxycyclopentane-1-carboxylate [(+/-)-1] and ethyl (+/-)-5-hydroxycyclopent-1-enecarboxylate [(+/-)-2] was demonstrated to undergo hydrolysis, as a side-reaction, during asymmetric (E > 200) O-acylation with Candida antarctica lipase B (CAL-B) as catalyst and vinyl acetate as acyl donor in t-BuOMe at 30 degrees C. This competition of acylation and undesirable hydrolysis draws attention to CAL-B-catalyzed non-hydrolytic resolutions where the substrates contain any hydrolysable functions. Enantiomerically enriched cis-2-hydroxycyclopentane-1-carboxylic acid (ee = 90%) and 5-hydroxycyclopent-1-enecarboxylic acid (ee = 47%) were prepared through de nova CAL-B-catalyzed hydrolysis of (+/-)-1 and (+/-)-2 with added H2O in t-BuOMe at 30 degrees C. (C) 2013 Elsevier B.V. All rights reserved.