(2S)-2-methyl-1,2-pentanediol | 133964-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-methyl-1,2-pentanediol
• 英文别名: (2S)-2-methylpentane-1,2-diol；(S)-2-Methylpentan-1,2-diol
• CAS: 133964-47-3
• 化学式: C₆H₁₄O₂
• 分子量: 118.176
• InChiKey: XERGTCWVYOKNAV-LURJTMIESA-N

物化性质

• 沸点：
  195.0±8.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-methyl-1,2-pentanediol 在 20percent Pd(OH)2 on carbon 4 A molecular sieve 、 Celite 、 三氟化硼乙醚 、 氢气 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 58.0h， 生成 tert-butyl (2S)-2-((1S,2S)-2-methoxy-2-methyl-1-((tritylsulfenyl)amino)pentyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  Enantioselective Synthesis of Antiinfluenza Compound A-315675

  摘要：

  Drug discovery efforts at Abbott Laboratories have led to the identification of influenza neuraminidase inhibitor A-315675 (1) as a candidate for development as an antiinfluenza drug. A convergent, stereoselective synthesis of this highly functionalized pyrrolidine is reported that utilizes pyrrolinone 2 as the key intermediate. The C5, C6 stereochemistry was established through a diastereoselective condensation of chiral imine compound 3 with silyloxypyrrole 4 to give pyrrolinone 2. The stereochemical outcome of this reaction depended critically on the choice of the imine functional group (FG), with tritylsulfenyl and (R)-toluenesulfinyl providing the desired products in good yields as crystalline intermediates. Conversion of pyrrolinone 2 into 1 was accomplished in seven subsequent steps, including Michael addition of cis-1-propenylcuprate at C4 and introduction of a cyano group as a carboxylic acid equivalent at C2.

  DOI：

  10.1021/jo0162890
• 作为产物：
  描述：

  (2E)-2-methyl-2-penten-1-ol 在 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 D-(-)-酒石酸二甲酯 、 三乙胺 、 三甲氧基磷 作用下， 以 四氢呋喃 、 癸烷 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2S)-2-methyl-1,2-pentanediol
  参考文献：
  名称：

  Enantioselective Synthesis of Antiinfluenza Compound A-315675

  摘要：

  Drug discovery efforts at Abbott Laboratories have led to the identification of influenza neuraminidase inhibitor A-315675 (1) as a candidate for development as an antiinfluenza drug. A convergent, stereoselective synthesis of this highly functionalized pyrrolidine is reported that utilizes pyrrolinone 2 as the key intermediate. The C5, C6 stereochemistry was established through a diastereoselective condensation of chiral imine compound 3 with silyloxypyrrole 4 to give pyrrolinone 2. The stereochemical outcome of this reaction depended critically on the choice of the imine functional group (FG), with tritylsulfenyl and (R)-toluenesulfinyl providing the desired products in good yields as crystalline intermediates. Conversion of pyrrolinone 2 into 1 was accomplished in seven subsequent steps, including Michael addition of cis-1-propenylcuprate at C4 and introduction of a cyano group as a carboxylic acid equivalent at C2.

  DOI：

  10.1021/jo0162890

文献信息

• SPIRO-OXINDOLE MDM2 ANTAGONISTS
  申请人：Wang Shaomeng

  公开号：US20110112052A1

  公开（公告）日：2011-05-12

  Provided herein are compounds, compositions, and methods in the field of medicinal chemistry. The compounds and compositions provided herein relate to spiro-oxindoles which function as antagonists of the interaction between p53 and MDM2, and their use as therapeutics for the treatment of cancer and other diseases.

  本文提供了关于药物化学领域的化合物、组合物和方法。本文提供的化合物和组合物涉及作为p53和MDM2相互作用拮抗剂的螺环氧吲哌酮，并且它们作为治疗癌症和其他疾病的药物的用途。
• Process for the preparation of substituted pyrrolidine neuraminidase inhibitors
  申请人：——

  公开号：US20030055297A1

  公开（公告）日：2003-03-20

  A process for the preparation of neuraminidase inhibitors having structural formula (28) 1 or therapeutically acceptable salts thereof, in which R 1 is alkyl, cycloalkyl, cycloalkylalkyl, or arylalkyl; R 2 is alkyl, cycloalkyl, cycloalkylalkyl, or arylalkyl; R 4 is alkyl, cycloalkyalkyl, or aryl-(C 2 -C 4 -alkyl); R 10 is methyl, ethyl, iso-propyl, or vinyl; and R 12 is hydrogen or alkyl and intermediates useful for the process are disclosed.

  一种用于制备具有结构式（28）1或其治疗上可接受的盐的神经氨酸酶抑制剂的方法，其中R1是烷基，环烷基，环烷基烷基或芳基烷基；R2是烷基，环烷基，环烷基烷基或芳基烷基；R4是烷基，环烷烷基或芳基（C2-C4-烷基）；R10是甲基，乙基，异丙基或乙烯基；和R12是氢或烷基，公开了用于该方法的中间体。
• <i>C</i>-Metallierte chirale Aloxide als d²- und d<b>3</b>-Reagenzien für die Synthese enantiomerenreiner Produkte (EPC-Synthese)
  作者：Carmen Nájera、Miguel Yus、Dieter Seebach

  DOI：10.1002/hlca.19840670135

  日期：1984.2.1

  C-Metallated Chiral Alkoxides as d2–-and d3 -Regents for the Synthesis of Enantiomerically Pure Compounds (EPC-Synthesis)

  C-金属化的手性醇盐，作为d 2-和d 3-试剂用于对映体纯化合物的合成（EPC合成）
• Inhibitors of neuraminidases
  申请人：——

  公开号：US20040097471A1

  公开（公告）日：2004-05-20

  Disclosed are compounds of the formula: 1 which are useful for inhibiting neuraminidases from disease-causing microorganisms, especially, influenza neuraminidase. Also disclosed are compositions and methods for preventing and treating diseases caused by microorganisms having a neuraminidase, processes for preparing the compounds and synthetic intermediates used in these processes.

  本发明涉及以下式子的化合物：1，该化合物对于抑制疾病引起微生物的神经氨酸酶，特别是流感神经氨酸酶非常有用。本发明还涉及预防和治疗由具有神经氨酸酶的微生物引起的疾病的组合物和方法，以及用于制备这些化合物和合成中间体的过程。
• NAJERA, C.;YUS, M.;SEEBACH, D., HELV. CHIM. ACTA, 1984, 67, N 1, 289-300
  作者：NAJERA, C.、YUS, M.、SEEBACH, D.

  DOI：——

  日期：——