(2R)-4-hydroxy-2-(2-phenylethyl)-2-propyl-3H-pyran-6-one | 221129-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R)-4-hydroxy-2-(2-phenylethyl)-2-propyl-3H-pyran-6-one
• CAS: 221129-55-1
• 化学式: C₁₆H₂₀O₃
• 分子量: 260.333
• InChiKey: BQCOYEHIANYPOM-MRXNPFEDSA-N

物化性质

• 沸点：
  421.6±45.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (2R)-4-hydroxy-2-(2-phenylethyl)-2-propyl-3H-pyran-6-one 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 5-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-5H-dibenzo[b,f]azepine 、 palladium 10% on activated carbon 、 氢气 、 ytterbium(III) triflate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 31.0h， 生成 (6R)-3-[(1R)-1-(3-Aminophenyl)propyl]-5,6-dihydro-4-hydroxy-6-(2-phenylethyl)-6-propyl-2H-pyran-2-one
  参考文献：
  名称：

  CN116730993

  摘要：

  公开号：

文献信息

• Synthesis of [¹⁴C] - and [¹³C₆]-labeled tipranavir and its potential hydroxyl metabolite and the glucuronide conjugate
  作者：Bachir Latli、Matt Hrapchak、John A. Easter、Wayne T. Stolle、Karl Grozinger、Dhileepkumar Krishnamurthy、Chris H. Senanayake

  DOI：10.1002/jlcr.1528

  日期：2008.7

  Tipranavir or Aptivus® is a non-peptidic protease inhibitor approved for the combination treatment with ritonavir of HIV infection. Tipranavir labeled with radioactive and stable isotopes of carbon was required for drug metabolism (excretion, distribution, and absorption) studies and to develop bioanalytical methods needed for the support of clinical studies. [7-14C]-Benzoic acid and uniformly labeled benzoic acid (ring-13C6 99 at% 13C) were used to prepare [14C]- and [13C6]-labeled tipranavir, respectively. Radioactively labeled tipranavir was prepared with a specific activity of 54 mCi/mmol (2GBq/mmol); it was necessary to dilute its specific activity with unlabeled tipranavir to 28 mCi/mmol (46.45 µCi/mg) because of its instability. The N-hydroxyl metabolite (12) and the glucuronide conjugate (13), the most abundant metabolites of tipranavir (when administered in conjunction with ritonavir) were also synthesized. Copyright © 2008 John Wiley & Sons, Ltd.

  替普瑞那韦或 Aptivus® 是一种非肽蛋白酶抑制剂，已被批准与利托那韦联合治疗艾滋病病毒感染。在进行药物代谢（排泄、分布和吸收）研究和开发支持临床研究所需的生物分析方法时，需要使用放射性和稳定碳同位素标记的替普瑞那韦。[7-14C]-苯甲酸和均匀标记的苯甲酸（环-13C6 99 at% 13C）分别用于制备[14C]-和[13C6]-标记的替拉那韦。放射性标记的替拉那韦的比活度为 54 mCi/mmol（2GBq/mmol）；由于其不稳定性，必须用未标记的替拉那韦将其比活度稀释至 28 mCi/mmol（46.45 µCi/mg）。此外，还合成了替拉那韦最丰富的代谢物 N- 羟基代谢物 (12) 和葡萄糖醛酸结合物 (13)（与利托那韦同时服用时）。Copyright © 2008 John Wiley & Sons, Ltd. All Rights Reserved.
• Process for the synthesis of an antiviral compound
  申请人：Honeywell International, Inc.

  公开号：US20040110957A1

  公开（公告）日：2004-06-10

  In a process comprising synthesizing pyranes including [R—(R*,R*)]-N-[3-[1-[5,6-dihydro-4-hydroxy-2-oxo-6-(2-phenylethyl)-6-propyl-2H-pyran-3-yl]propyl]phenyl]-5-(trifluoromethyl)-2-pyridinesulfonamide the present invention comprises the improvements comprising: (a) providing a racemic mixture of 3-hydroxy-3-(2-phenylethyl)-hexanoate ethyl acetate by reacting said 1-phenyl-hexan-3-one with ethylbromoacetate under Reformatsky conditions; and (b) separating (R)-3-hydroxy-3-(2-phenylethyl)-hexanoic acid in enantiomeric excess by saponification and reverse resolution of the racemate of step (a) to produce a resolved product. In addition, the present invention comprises a reverse resolution process for separating an enantiomer from a mixture of enantiomers.

  本发明涉及合成吡喃类化合物的方法，包括合成 [R—(R*,R*)]-N-[3-[1-[5,6-二氢-4-羟基-2-氧代-6-(2-苯乙基)-6-丙基-2H-吡喃-3-基]丙基]苯基]-5-(三氟甲基)-2-吡啶磺酰胺的改进。所述改进包括：(a)通过在Reformatsky条件下将1-苯基己酮与溴乙酸乙酯反应，提供3-羟基-3-(2-苯乙基)己酸乙酯的外消旋体混合物；(b)通过皂化和反向分离步骤(a)的外消旋体，分离出(R)-3-羟基-3-(2-苯乙基)己酸，以产生一个分离的产物。此外，本发明还涉及从对映体混合物中分离对映体的反向分离方法。
• [EN] PROCESS TO PRODUCE 4-HYDROXY-2-OXO-PYRANE DERIVATES USEFUL AS PROTEASE INHIBITORS<br/>[FR] PROCEDE DE PRODUCTION DE DERIVES DE 4-HYDROXY-2-OXO-PYRANE UTILES EN TANT QU'INHIBITEURS DE PROTEASE
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：WO1999012919A1

  公开（公告）日：1999-03-18

  (EN) Disclosed is a novel process and novel intermediates to prepare [R-(R*,R*) ]-N-[3-[1-[5, 6-dihydro-4-hydroxy -2-oxo-6-(2-phenylethyl) -6-propyl-2H-pyran-3- yl]propyl]phenyl]-5- (trifluoromethyl)-2- pyridinesulfonamide (XIX) which is a protease inhibitor useful in treating humans infected with the HIV virus.(FR) L'invention concerne un nouveau procédé de préparation et de nouveaux produits intermédiaires permettant de préparer [R-(R*,R*) ]-N-[3-[1-[5, 6-dihydro-4-hydroxy -2-oxo-6-(2-phényléthyl) -6-propyl-2H-pyran-3- yl]propyl]phényl]-5- (trifluorométhyl)-2- pyridinesulfonamide (XIX), qui est un inhibiteur de protéase utile pour traiter les humains atteints du virus VIH.

  揭示了一种新的工艺和新的中间体，用于制备[R-(R*,R*)]-N-[3-[1-[5,6-二氢-4-羟基-2-氧代-6-(2-苯乙基)-6-丙基-2H-吡喃-3-基]丙基]苯基]-5-(三氟甲基)-2-吡啶磺酰胺(XIX)，该化合物是一种蛋白酶抑制剂，可用于治疗感染HIV病毒的人类。
• Immunoassays, Haptens, Immunogens and Antibodies for Anti-HIV Therapeutics
  申请人：Valdez Johnny

  公开号：US20070218486A1

  公开（公告）日：2007-09-20

  This invention provides compounds, methods, immunoassays, and kits relating to active, metabolically sensitive (“met-sensitive”) moieties of anti-HIV therapeutics, such as HIV protease inhibitors (PI), HIV nucleoside reverse transcriptase inhibitors (NRTI) and HIV entry inhibitors (EII).

  本发明提供了与抗HIV治疗中的活性、代谢敏感（“代谢敏感”）分子相关的化合物、方法、免疫测定和试剂盒，例如HIV蛋白酶抑制剂（PI）、HIV核苷类逆转录酶抑制剂（NRTI）和HIV进入抑制剂（EII）。
• Cellular accumulation of phosphonate analogs of hiv protease inhibitor compounds
  申请人：Arimilli N. Murty

  公开号：US20070010489A1

  公开（公告）日：2007-01-11

  Phosphonate substituted compounds with HIV protease inhibitory properties having use as therapeutics and for other industrial purposes are disclosed. The compositions inhibit 5 HIV protease activity and/or are useful therapeutically for the treatment of AIDS and other antiviral infections, as well as in assays for the detection of HIV protease.

  本发明揭示了具有HIV蛋白酶抑制剂性质的膦酸酯取代化合物，其具有作为治疗剂和其他工业用途的用途。该组合物抑制5型HIV蛋白酶活性和/或在治疗艾滋病和其他抗病毒感染方面具有治疗作用，以及在检测HIV蛋白酶方面的检测中有用。