5-(R)-(furan-3-yl)-5-hydroxy-3-oxo-pentanoic acid methyl ester | 212969-19-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 5-(R)-(furan-3-yl)-5-hydroxy-3-oxo-pentanoic acid methyl ester
• 英文别名: (5R)-methyl 5-[furan-3-yl]-5-hydroxy-3-oxopentanoate；(5R)-5-(furan-3-yl)-5-hydroxy-3-oxo-pentanoic acid；methyl (5R)-5-(furan-3-yl)-5-hydroxy-3-oxopentanoate
• CAS: 212969-19-2
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: YAJHFXJSMLQLLG-SECBINFHSA-N

物化性质

• 沸点：
  225.1±23.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(R)-(furan-3-yl)-5-hydroxy-3-oxo-pentanoic acid methyl ester 在 lithium hydroxide 、 zinc(II) tetrahydroborate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 生成 (5R)-5-(furan-3-yl)-3,5-dihydroxy-2-methylpentanoic acid methyl ester
  参考文献：
  名称：

  Stereochemistry of Antiinflammatory Marine Sesterterpenes

  摘要：

  DOI：

  10.1002/(sici)1099-0690(200003)2000:6<947::aid-ejoc947>3.0.co;2-u
• 作为产物：
  描述：

  6-[(2R)-2-(furan-3-yl)-2-hydroxy-ethyl]-2,2-dimethyl-1,3-dioxin-4-one 以 甲醇 、 甲苯 为溶剂， 生成 5-(R)-(furan-3-yl)-5-hydroxy-3-oxo-pentanoic acid methyl ester
  参考文献：
  名称：

  首次对映选择性合成马诺利德：醛-二恶英对映选择性缩合的应用

  摘要：

  Manoalide是一种止痛和消炎性的酯基萜烯，是首次立体选择性地合成的。C-4立体生成中心已通过使用Ti（O i Pr）4 /（R）-（+）-二元醇复合物的对映选择性羟醛缩合在较早的阶段引入。

  DOI：

  10.1016/s0957-4166(99)00529-7

文献信息

• Enantioselective Synthesis of Pyranofuranone Moieties of Manoalide and Cacospongionolide B by Enzymatic and Chemical Approach
  作者：Margherita De Rosa、Annunziata Soriente、Guido Sodano、Arrigo Scettri

  DOI：10.1016/s0040-4020(00)00122-8

  日期：2000.3

  Two synthetic sequences leading to the pyranofuranone moieties of Manoalide and Cacospongionolide B in enantiomerically enriched forms are reported. The key steps involve either an enantioselective aldol condensation or an enzymatic resolution.

  报道了导致对映异构体富集形式的Manoalide和Cacospongionolide B的吡喃呋喃酮部分的两个合成序列。关键步骤涉及对映选择性羟醛缩合或酶促拆分。
• An efficient asymmetric aldol reaction of Chan's diene promoted by chiral Ti(IV)–BINOL complex
  作者：Annunziata Soriente、Margherita De Rosa、Marina Stanzione、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/s0957-4166(01)00150-1

  日期：2001.4

  1.3-Bis-(trimethylsilyloxy)-1-methoxy-buta-1,3-diene (Chan's diene) can be conveniently used in asymmetric aldol reaction with aromatic, heteroaromatic, alpha,beta -unsaturated and aliphatic aldehydes in the presence of catalytic amounts (2-8% mol) of chiral Ti(IV)/(R)-BINOL complex. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A new procedure for the enantioselective vinylogous aldol reaction of Chan’s diene
  作者：Rosaria Villano、Maria Rosaria Acocella、Antonio Massa、Laura Palombi、Arrigo Scettri

  DOI：10.1016/j.tetasy.2006.12.016

  日期：2006.12

  Chiral delta-hydroxy-delta-ketoesters are easily available through the enantio selective vinylogous aldol reaction of Chan's diene promoted by a SiCl4/chiral phosphoramide catalytic system. The procedure is conveniently exploited for a very rapid approach to (+)-kavain, a natural bio-active alpha-pyrone compound. (c) 2007 Elsevier Ltd. All rights reserved.
• An easy approach to chiral non-racemic 6-(furan-3-yl)-5,6-dihydro-pyran-2-ones
  作者：Annunziata Soriente、Margherita De Rosa、Patrizia Dovinola、Guido Sodano、Arrigo Scettri

  DOI：10.1016/s0957-4166(98)00210-9

  日期：1998.7

  Chiral non-racemic 6-(furan-3-yl)-pyran-2-one derivatives, key-intermediates in the preparation of compactin, manoalide and cacospongionolide subunits, are easily accessible through a rapid and convenient six-step sequence. (C) 1998 Elsevier Science Ltd. All rights reserved.
• First enantioselective synthesis of manoalide: application of aldehyde–dioxinone enantioselective condensation
  作者：Annunziata Soriente、Margherita De Rosa、Aniello Apicella、Arrigo Scettri、Guido Sodano

  DOI：10.1016/s0957-4166(99)00529-7

  日期：1999.12

  Manoalide, an analgesic and anti-inflammatory sesterterpene, has been stereoselectively synthesized for the first time. The C-4 stereogenic centre has been introduced in an early step by enantioselective aldol condensation using a Ti(OiPr)4/(R)-(+)-binol complex.

  Manoalide是一种止痛和消炎性的酯基萜烯，是首次立体选择性地合成的。C-4立体生成中心已通过使用Ti（O i Pr）4 /（R）-（+）-二元醇复合物的对映选择性羟醛缩合在较早的阶段引入。