methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate | 127061-46-5

• 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: methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate
• 英文别名: (-)-methyl (1S,4R)-4-acetamidocyclopent-2-ene-1-carboxylate；methyl cis-4-acetamidocyclopent-2-enecarboxylate；Methyl-cis-4-acetamidocyclopent-2-encarboxylat；(1R,4S)-rel-4-(Acetylamino)-2-cyclopentene-1-carboxylic Acid Methyl Ester；methyl (1S,4R)-4-acetamidocyclopent-2-ene-1-carboxylate
• CAS: 127061-46-5
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: NEJBWENICROWTO-SFYZADRCSA-N

物化性质

• 沸点：
  337.8±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate 在 palladium on activated charcoal calcium borohydride 、 水 、 氢气 、 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 137.0h， 生成
  参考文献：
  名称：

  An approach to a carbocyclic analogue of cyclic adenosine 5′-diphosphate ribose. The synthesis and bisphosphorylation of N1-[(1S, 3R)-3-(Hydroxymethyl)cyclopent-1-yl]inosine

  摘要：

  The synthesis of N-1-[(1S, 3R)-3-(hydroxymethyl)cyclopent-1-yl]inosine (11) via a cyclocondensation route is reported. Regioselective bisphosphorylation of the primary 5'-hydroxyl groups leads to a carbocyclic, inosine analogue of seco adenosine 5'-diphosphate ribose (3). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01175-1
• 作为产物：
  描述：

  2-氮杂双环[2.2.1]庚-5-烯-3-酮 在 吡啶 、 盐酸 、 sodium hydroxide 、 硫酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 61.0h， 生成 methyl (+)-cis-4-acetamidocyclopent-2-enecarboxylate
  参考文献：
  名称：

  Biocatalytical transformations. IV. Enantioselective enzymatic hydrolyses of building blocks for the synthesis of carbocyclic nucleosides.

  摘要：

  Enantiomerically pure alkyl(1S, 4R)- and (1R, 4S)-4-acetamido-cyclopent-2-enecarboxylates are obtained from their corresponding racemates by hydrolysis with PLE or the lipase from Candida cylindrucea.

  DOI：

  10.1016/s0957-4166(00)86183-2

文献信息

• Novel intermediates for the preparation of Carbovir
  申请人：Hoffmann-La Roche Inc.

  公开号：US04939252A1

  公开（公告）日：1990-07-03

  The invention provides novel cyclopentenyl carbinol compounds which are useful as intermediates for the preparation of the anti-AIDS drug, Carbovir. Processes for the preparation of such novel compounds and for the use of the compounds to make Carbovir are also provided.

  该发明提供了一种新型的环戊烯基醇化合物，可用作制备抗艾滋病药物卡波韦的中间体。还提供了制备这种新型化合物以及利用这些化合物制备卡波韦的方法。
• Biocatalytical transformations—VI. The 4-acetamido-cyclopent-2-ene carboxylate route revisited: Synthesis of (+)- and (−)-aristeromycin
  作者：René Csuk、Petra Dörr

  DOI：10.1016/0040-4020(95)00246-5

  日期：1995.5

  Enantiomerically pure (+)- as well as (−)-aristeromycin can be synthesized starting from (+)- or (−)-butyl (or hexyl) 4-acetamido-cyclopent-2-ene carboxylate; these carboxylates are easily obtained from their corresponding racemates by hydrolysis with the lipase from Candida rugosa.

  对映体纯的（+）-以及（-）-阿霉素可以从4-乙酰氨基-环戊-2-烯的（+）-或（-）-丁基（或己基）羧酸酯开始合成；这些羧酸盐很容易通过用来自假丝酵母的脂肪酶水解从它们相应的外消旋物中获得。
• Substituent and solvent effects in the 1,3-dipolar cycloadditions for synthesis of anti-influenza agent peramivir and its analog
  作者：Chien-Liang Chen、Tzu-Wei Chiu、Yung-Wen Chen、Jim-Min Fang

  DOI：10.1016/j.tet.2019.06.023

  日期：2019.8

  anti-influenza drug targeting the virus neuraminidase. The (3 + 2) cycloaddition reaction of 2-ethylbutanenitrile oxide with the cyclopentene dipolarophile derived from Vince lactam is a key step in the conventional synthesis of peramivir. Our study showed that conducting the (3 + 2) cycloaddition reactions with either aliphatic or aromatic nitrile oxide in hexane solution provided high percentage of the desired

  流感仍然是人类的健康问题。Peramivir是FDA批准的针对病毒神经氨酸酶的抗流感药物。2-乙基丁烯腈氧化物与衍生自文斯内酰胺的环戊烯双极性亲和剂的（3 + 2）环加成反应是常规合成帕拉米韦的关键步骤。我们的研究表明，与脂肪族或芳香族腈氧化物在己烷溶液中进行（3 + 2）环加成反应可提供较高百分比的所需区域异构体，并且具有吸电子性质的N-取代基也有利于区域选择性。这项研究还证明了（-）-peramivir和具有苯基取代3-戊基部分的类似物的另一种合成途径。
• Adenosine deaminase resistant antiviral purine arabinonucleosides
  申请人：Regents of the University of Minnesota

  公开号：US04383114A1

  公开（公告）日：1983-05-10

  The preparation of 9-[.alpha.-(2.alpha.,3.beta.-dihydroxy-4.alpha.-(hydroxymethyl) cyclopentyl)]-6-substituted purines: ##STR1## and their derivatives wherein R is amino, mercapto, methylmercapto, hydroxy, halogen, or substituted amino: ##STR2## wherein R' and R" may be the same or different and are hydrogen, methyl, ethyl, propyl or phenyl. The compounds exhibit anti-viral and antitumor activity and are resistant to adenosine deaminase. Acid salts and esters of the purine nucleosides have also been prepared.

  9-[.alpha.-(2.alpha.,3.beta.-二羟基-4.alpha.-(羟甲基)环戊基)]-6-取代嘌呤的制备：##STR1##及其衍生物，其中R是氨基、巯基、甲硫基、羟基、卤素或取代氨基：##STR2##其中R'和R"可能相同或不同，是氢、甲基、乙基、丙基或苯基。这些化合物具有抗病毒和抗肿瘤活性，并且对腺苷脱氨酶具有抗性。此外，嘌呤核苷酸的酸盐和酯也已制备。
• Adenosine deaminase resistant antiviral purine nucleosides and method of
  申请人：The Regents of the University of Minnesota

  公开号：US04223156A1

  公开（公告）日：1980-09-16

  The preparation of (+)-9-[.alpha.-(2.alpha.,3.beta.-dihydroxy-4.alpha.-(hydroxymethyl)cyclope ntyl)]-6-substituted purines: ##STR1## and (+)-3-[.alpha.-(2.alpha.,3.beta.-dihydroxy-4.alpha.-(hydroxymethyl)cyclope ntyl)]7-substituted-v-triazolo[4,5d]pyrimidines: ##STR2## and their derivatives wherein R is amino, mercapto, methylmercapto, hydroxy, halogen, or substituted amino: ##STR3## wherein R' and R" may be the same or different and are of hydrogen, methyl, ethyl, propyl or phenyl. The preparation of the single intermediate from which either of these series of compounds may be synthesized is also disclosed. The compounds exhibit antiviral and antitumor activity.

  (+)-9-[.alpha.-(2.alpha.,3.beta.-二羟基-4.alpha.-(羟甲基)环戊基)]-6-取代嘌呤的制备方法：##STR1## 和(+)-3-[.alpha.-(2.alpha.,3.beta.-二羟基-4.alpha.-(羟甲基)环戊基)]7-取代-v-三唑[4,5d]嘧啶的制备方法：##STR2## 以及它们的衍生物，其中R为氨基、巯基、甲硫基、羟基、卤素或取代氨基：##STR3## 其中R'和R"可以相同也可以不同，分别为氢、甲基、乙基、丙基或苯基。本文还披露了制备这两系列化合物的单一中间体的方法。这些化合物具有抗病毒和抗肿瘤活性。