DL-trans-4-acetoxy-2-cyclopentenol | 60410-17-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: DL-trans-4-acetoxy-2-cyclopentenol
• 英文别名: (1R,4R)-4-hydroxycyclopent-2-en-1-yl acetate；[(1R,4R)-4-hydroxycyclopent-2-en-1-yl] acetate
• CAS: 60410-17-5
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: IJDYOKVVRXZCFD-BQBZGAKWSA-N

物化性质

• 沸点：
  208.0±40.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  DL-trans-4-acetoxy-2-cyclopentenol 在 potassium cyanide 、 四氧化锇 、 偶氮二甲酸二异丙酯 、 水 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 26.5h， 生成 (1R,3R,4S)-4-(6-chloro-9H-purin-9-yl)-4-hydroxy-2,3-(isopropylidenedioxy)cyclopent-1-one
  参考文献：
  名称：

  The 4′,4′-difluoro analog of 5′-noraristeromycin: A new structural prototype for possible antiviral drug development toward orthopoxvirus and cytomegalovirus

  摘要：

  As a surrogate for 4'-hydroxy-5'-noraristeromycin and related carbocyclic nucleosides, an efficient, enantiodivergent synthetic route to both enantiomers of 5-(6-amino-9H-purin-9-yl)-3,3-difluorocyclopentane-1,2-diol (6 and ent-6) has been developed from a common starting material ((+)-(IR,4S)-4-hydroxy-2-cyclopenten-1-yl acetate, 10). Both compounds were assayed versus a series of viruses. The only response found was for compound 6 toward vaccinia and cowpox (EC50 Of 143 and 94 mu M, respectively) and human cytomegalovirus (EC50 of 6.2 mu M). Both compounds were non-cytotoxic. While not as active as cidofovir toward the orthopox viruses and ganciclovir toward cytomegalovirus, compound 6 offers a new structural prototype upon which to build for uncovering new agents effective against these viral types. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.044
• 作为产物：
  描述：

  2,4-戊二酮,1,5-二氯 在 Grubbs catalyst first generation 、 正丁基锂 、 [(S)-2,2'-双(二苯基磷)-1,1'-联萘]二氯化钌(II) 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 DL-trans-4-acetoxy-2-cyclopentenol
  参考文献：
  名称：

  Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones

  摘要：

  Protected 4-hydroxycyclopentenones (4-HCPs) constitute an important class of intermediates in chemical synthesis. A route to this class of compound has been developed. Key steps include Noyori reduction (which establishes the stereochemistry of the product), ring-closing metathesis, and simple functional group conversions to provide a set of substituted 4-HCPs in either enantiomeric form.

  DOI：

  10.1021/jo402539p

文献信息

• Stable and easily available sulfide surrogates allow a stereoselective activation of alcohols
  作者：Jérémy Merad、Ján Matyašovský、Tobias Stopka、Bogdan R. Brutiu、Alexandre Pinto、Martina Drescher、Nuno Maulide

  DOI：10.1039/d1sc01602d

  日期：——

  Isothiouronium salts are easily accessible and stable compounds. Herein, we report their use as versatile deoxasulfenylating agents enabling a stereoselective, thiol-free protocol for synthesis of thioethers from alcohols. The method is simple, scalable and tolerates a broad range of functional groups otherwise incompatible with other methods. Late-stage modification of several pharmaceuticals provides

  异硫脲鎓盐是容易获得且稳定的化合物。在本文中，我们报道了它们作为通用的脱氧亚磺酰化剂的用途，从而能够从醇类中合成立体选择性，无硫醇的方案。该方法简单，可扩展，并且可以承受广泛的官能团，否则这些官能团将与其他方法不兼容。几种药物的后期修饰可提供生物相关分子的多种类似物。进行的实验深入了解了反应机理。
• Preparative Bioorganic Chemistry; 8.¹Efficient Enzymatic Preparation of (1<i>R</i>,4<i>S</i>)-(+)-4-Hydroxy-2-cyclopentenyl Acetate
  作者：Takeshi Sugai、Kenji Mori

  DOI：10.1055/s-1988-27454

  日期：——

  An efficient method for the preparation of (1R,4S)-(+)- 4-hydroxy-2-cyclopentenyl acetate, a useful chiral starting material for the synthesis of prostaglandins, is described. A mixture of cis- and trans-3,5-diacetoxycyclopentene, readily obtainable on a preparative laboratory scale, was used as the substrate for the hydrolysis with commercially available pig pancreatic lipase (PPL). PPL hydrolyzed the substrate enantioselectively and substrate-selectively, yielding mainly the (+)-cis-monoacetate and trans-diacetate (Method A). The former was recrystallized to give the diastereomerically and optically pure (+)- cis-monoacetate. Ester exchange of cis/trans mixture of the diacetate in an organic solvent using enzymes as batch or flow system was also investigated (Method B). Method A was applicable to 0.25 mol of substrate, and yielded 0.127 mol (18 g, 51%) of optically pure (+)-monoacetate with recycling recovered materials.

  描述了一种高效制备(1R,4S)-(+)-4-羟基-2-环戊烯基乙酸酯的方法，这是一种用于合成前列腺素的有用手性起始材料。使用的底物是cis和trans-3,5-二乙酰氧基环戊烯的混合物，这种混合物可以在实验室规模上轻松获得。将其用商业可得的猪胰脂肪酶（PPL）水解。PPL对底物进行了选择性水解，主要产生(+) - cis-单乙酸酯和trans-二乙酸酯（方法A）。前者经过重结晶得到立体异构体和光学纯的(+) - cis-单乙酸酯。还研究了在有机溶剂中利用酶进行的cis/trans-二乙酸酯混合物的酯交换，采用批量或流动系统（方法B）。方法A适用于0.25摩尔的底物，产生0.127摩尔（18克，51%）的光学纯(+) - 单乙酸酯，并回收再利用材料。
• [EN] PROCESS FOR MAKING BERAPROST<br/>[FR] PROCÉDÉ DE PRÉPARATION DE BÉRAPROST
  申请人：UNITED THERAPEUTICS CORP

  公开号：WO2017027706A1

  公开（公告）日：2017-02-16

  A method is described for making single isomers of synthetic beraprost diol, a key intermediate for making 314-d isomer of beraprost. The method requires fewer steps than the known methods for making these compounds and can be used to scale up the reaction more easily to produce commercial quantities.

  本文描述了一种制备合成beraprost二醇单异构体的方法，这是制备314-d异构体beraprost的关键中间体。该方法比已知方法需要更少的步骤，并且可以更容易地扩大反应规模以生产商业数量。
• PROCESS FOR MAKING BERAPROST
  申请人：United Therapeutics Corporation

  公开号：US20180037563A1

  公开（公告）日：2018-02-08

  A method is described for making single isomers of synthetic beraprost diol, a key intermediate for making 314-d isomer of beraprost. The method requires fewer steps than the known methods for making these compounds and can be used to scale up the reaction more easily to produce commercial quantities.

  本文描述了一种制备合成贝拉前列素二醇单异构体的方法，该方法是制备314-d异构体贝拉前列素的关键中间体。该方法所需步骤比已知方法少，可以更容易地扩大反应规模以生产商业数量。
• [EN] NOVEL PYRROLO[2,3-D]PYRIMIDINES AND THEIR USE AS TYROSINE KINASE INHIBITORS<br/>[FR] NOUVELLES PYRROLO(2,3-D)PYRIMIDINES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE TYROSINE KINASE
  申请人：NOVARTIS AG

  公开号：WO1997028161A1

  公开（公告）日：1997-08-07

  (EN) Described are pyrrolo[2,3-d]pyrimidines of formula (I) wherein R1-R4 are as defined in the description. The compounds have valuable pharmaceutical properties and are effective especially as tyrosine protein kinase inhibitors. They can be used in warm-blooded animals in the treatment of bone diseases and other diseases that can be favourably influenced by the inhibition of tyrosine protein kinase.(FR) Cette invention concerne des pyrrolo(2,3-d)pyrimidines représentées par la formule (I) dans laquelle R1, R2, R3 et R4 sont définis dans le descriptif de l'invention. Ces composés possèdent d'intéressantes propriétés pharmaceutiques et s'avèrent particulièrement efficaces en tant qu'inhibiteurs de tyrosine protéine kinase. Ils peuvent permettre de traiter, chez des animaux à sang chaud, des maladies des os et d'autres maladies qui sont favorablement influencées par l'inhibition d'une tyrosine protéine kinase.

  描述了式(I)中R1-R4如描述中定义的吡咯并[2,3-d]嘧啶。这些化合物具有有价值的药物特性，特别是作为酪氨酸蛋白激酶抑制剂非常有效。它们可以用于温血动物中，治疗骨疾病和其他可以通过抑制酪氨酸蛋白激酶而受益的疾病。