(2R,4S)-5-hydroxy-2-methyl pentan-4-olide | 53078-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2R,4S)-5-hydroxy-2-methyl pentan-4-olide
• 英文别名: (3R,5S)-(+)-trans-5-hydroxymethyl-3-methyl-4,5-dihydro-2(3H)-furanone；3R,5S-5-hydroxymethyl-3-methyl-4,5-dihydro-2(3H)-furanone；(3R,5S)-5-(hydroxylmethyl)-3-methyldihydrofuran-2(3H)-one；Nbtgwkzofhsact-uhnvwzdzsa-；(3R,5S)-5-(hydroxymethyl)-3-methyloxolan-2-one
• CAS: 53078-05-0
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: NBTGWKZOFHSACT-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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,4S)-5-hydroxy-2-methyl pentan-4-olide 在 palladium on activated charcoal 盐酸 、 sodium azide 、 15-冠醚-5 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， -30.0~25.0 ℃ 、800.0 kPa 条件下， 反应 22.5h， 生成 3R,5S-5-aminomethyl-3-methyl-4,5-dihydro-2(3H)-furanone-hydrochloride
  参考文献：
  名称：

  Enantiopure DAVA-derivatives-part III. Synthesis of all 4 stereoisomers of 2-methyl-4-hydroxy-5-aminopentanoic acid (2-Me-4-OH-DAVA).

  摘要：

  A stereoselective synthesis of the 4 stereoisomers of 2-methyl-4-hydroxy-5-amino-pentanoic acid namely 2R,4S-9a, 2S,4S-9b, ent-9a and ent-9b is presented, starting from the known lactones S-1 and R-l, which are readily available from L- and D-glutamic acid. Only ent-9b shows affinity for GABA(B)-receptor sites.

  DOI：

  10.1016/s0957-4166(00)86022-x
• 作为产物：
  描述：

  5-(羟基甲基)二氢-2(3H)-呋喃酮 在 水 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 反应 3.0h， 生成 (2R,4S)-5-hydroxy-2-methyl pentan-4-olide
  参考文献：
  名称：

  Enantiopure DAVA-derivatives-part III. Synthesis of all 4 stereoisomers of 2-methyl-4-hydroxy-5-aminopentanoic acid (2-Me-4-OH-DAVA).

  摘要：

  A stereoselective synthesis of the 4 stereoisomers of 2-methyl-4-hydroxy-5-amino-pentanoic acid namely 2R,4S-9a, 2S,4S-9b, ent-9a and ent-9b is presented, starting from the known lactones S-1 and R-l, which are readily available from L- and D-glutamic acid. Only ent-9b shows affinity for GABA(B)-receptor sites.

  DOI：

  10.1016/s0957-4166(00)86022-x

文献信息

• Radical Additions of Alkyl 2-Haloalkanoates and 2-Haloalkanenitriles to Alkenes Initiated by Electron Transfer from Copper in Solvent-Free Systems
  作者：Jürgen O. Metzger、Ralf Mahler、Gerald Francke

  DOI：10.1002/jlac.199719971119

  日期：1997.11

  Alkyl 2-iodoalkanoates 2, and 2-iodoalkanenitriles 15 were added, with copper powder, to the 1-alkenes 1a, e, f, and h, and to the alkenes 1b, c, d, and g with a 1,2-dialkyl substituted double bond, to give, respectively, γ-lactones and 4-iodoalkanenitriles in very good yields. No solvent was used. The reaction is a free radical addition initiated by electron transfer from copper to the activated iodoalkane

  将2-碘代链烷酸烷基酯2和2-碘代链烷腈15与铜粉一起添加到1-链烯1a，e，f和h中，并添加到具有1,2-的链烯1b，c，d和g中。二烷基取代的双键，以非常好的收率分别得到γ-内酯和4-碘代烷基亚腈。不使用溶剂。该反应是由电子从铜转移到活化的碘代烷烃引发的自由基加成。使用各个溴代化合物的产率较低。通过向反应混合物中添加化学计量的碘化钠，原位形成碘化合物，可以提高产率。如果是溴溴丙二酸甲酯，则为6，证明不需要添加碘化钠。通过考虑在碘转移到手性加合物自由基过程中形成的过渡态取代基的空间相互作用，合理化了相对的1，3-不对称诱导引起的加成反应的非对映选择性。
• A transition metal-catalyzed enyne metathesis for the preparation of pyrrolizidine alkaloid core: Application towards the total synthesis of stemaphylline
  作者：Praveen Kumar、Md. Ataur Rahman、Ashanul Haque、Jhillu Singh Yadav

  DOI：10.1016/j.tetlet.2021.152906

  日期：2021.3

  In this paper, we disclose an efficient route for the synthesis of pyrrolizidine alkaloid core and its application towards the total synthesis of stemaphylline. The key pyrrolizidine core was achieved with Ru-carbene catalyzed ring closing enyne metathesis (RCEM). The effect of different types and amounts of Ru-carbene catalysts, solvents and temperature were systematically studied. The advantage of

  在本文中，我们公开了一种合成吡咯烷核生物碱核心的有效途径，并将其应用于柳杉碱的全合成。关键的吡咯嗪核核心是通过Ru-卡宾催化的闭环烯炔复分解（RCEM）实现的。系统研究了不同类型和数量的Ru-卡宾催化剂，溶剂和温度的影响。该方法的优点包括一次操作即可构建吡咯烷核生物碱核心。
• Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters
  作者：Sara Drioli、Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/s0957-4166(00)00057-4

  日期：2000.4

  Enantiomerically pure 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters are prepared by enzymatic resolution of the chiral racemic esters. Their stereochemistry as well as their absolute configurations have been established by chemical correlation. The influence of the alkoxycarbonyl group at C-2 and that of the methyl group at C-4 on the sign of the Cotton effect in their CD spectra have been investigated. Formation of enantiomerically pure hydroxydiesters, precursors of the above-mentioned gamma-lactones, by baker's yeast reduction of the corresponding ketodiesters was unsatisfactory. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Nishida, Yoshihiro; Konno, Masao; Fukushima, Yuko, Agricultural and Biological Chemistry, 1986, vol. 50, # 1, p. 191 - 194
  作者：Nishida, Yoshihiro、Konno, Masao、Fukushima, Yuko、Ohrui, Hiroshi、Meguro, Hiroshi

  DOI：——

  日期：——
• Enantiopure DAVA-derivatives-part III. Synthesis of all 4 stereoisomers of 2-methyl-4-hydroxy-5-aminopentanoic acid (2-Me-4-OH-DAVA).
  作者：Claus Herdeis、Karen Lütsch

  DOI：10.1016/s0957-4166(00)86022-x

  日期：1993.1

  A stereoselective synthesis of the 4 stereoisomers of 2-methyl-4-hydroxy-5-amino-pentanoic acid namely 2R,4S-9a, 2S,4S-9b, ent-9a and ent-9b is presented, starting from the known lactones S-1 and R-l, which are readily available from L- and D-glutamic acid. Only ent-9b shows affinity for GABA(B)-receptor sites.

表征谱图