(3S,4R)-3-Hydroxy-4-(iodomethyl)-γ-butyrolactone | 159811-83-3

• 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: (3S,4R)-3-Hydroxy-4-(iodomethyl)-γ-butyrolactone
• 英文别名: cis-4-Hydroxy-5-(iodomethyl)-4,5-dihydro-2(3H)-furanone；(4S,5R)-4-hydroxy-5-(iodomethyl)oxolan-2-one
• CAS: 159811-83-3
• 化学式: C₅H₇IO₃
• 分子量: 242.013
• InChiKey: QJIYRZUTCSEHHG-IMJSIDKUSA-N

物化性质

• 沸点：
  395.9±27.0 °C(predicted)
• 密度：
  2.139±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (3S,4R)-3-Hydroxy-4-(iodomethyl)-γ-butyrolactone 在 2,6-二甲基吡啶 、 正丁基锂 、 偶氮二异丁腈 、 三正丁基氢锡 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 56.0h， 生成 (E/Z)-(2S,3S)-3-<(tert-Butyldimethylsilyl)oxy>-5-octen-2-ol
  参考文献：
  名称：

  New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds

  摘要：

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].

  DOI：

  10.1021/jo00103a008
• 作为产物：
  描述：

  (S)-N-Benzyl-N-methyl-3-acetoxy-4-pentenamide 在 phosphate buffer (0.1 N, pH 7) 、 碘 作用下， 以 乙二醇二甲醚 、 水 、 丙酮 为溶剂， 反应 39.0h， 生成 (3S,4R)-3-Hydroxy-4-(iodomethyl)-γ-butyrolactone
  参考文献：
  名称：

  New Synthesis of All Four Isomers of 3-Hydroxy-4-methyl-.gamma.-butyrolactone by Stereoselective Intramolecular Lactonization. Application to Asymmetric Synthesis of Biologically Active Compounds

  摘要：

  A new synthesis of all four isomeric 3-hydroxy-4-methyl-gamma-butyrolactones (11, ent-11, 12, ent-12) has been performed. The former two were prepared via stereoselective iodolactonization, which favors the cis-3,4-disubstituted system (16a and ent-16a), of N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-13, readily available by resolution of the racemate by lipase-mediated transesterification; and the latter two were prepared via stereoselective oxylactonization, which favors the trans-3,4-disubstituted system [(3R,4S)-20a and ent-(3R,4S)-20a], of O-TBDMS-protected N-benzyl-N-methyl-3-hydroxy-4-pentenamides (R)- and (S)-14. Butyrolactones 11 and 12 have been readily transformed into biologically active compounds [(-)-blastmycinolactol (27), (-)-NFX-2 (2), (-)-NFX-4 (3), lipid metabolites 9 and 10, and the sex pheromone (-)-(2S,3S)-2,3-octanediol (30)].

  DOI：

  10.1021/jo00103a008

文献信息

• Iodocyclization of allylic alcohol derivatives containing internal nucleophiles. Control of stereoselectivity by substituents in the acyclic precursors
  作者：A. Richard Chamberlin、Milana Dezube、Patrick Dussault、Mark C. McMills

  DOI：10.1021/ja00356a020

  日期：1983.9

  La reaction d'acides hydroxy-3 alcene-4oiques avec l'iode en milieu biphasique neutre donne une cyclisation stereoselective habituellement en cis-hydroxy-3 iodo-4 lactone. Effet des substituants

  La 反应 d'acides hydroxy-3 alcene-4oiques avec l'iode en milieu biphasique neutre donne une 环化立体选择性习惯 en cis-hydroxy-3 iodo-4 内酯。替代物的作用
• Stereoselective iodolactonization of acyclic unsaturated 3-hydroxyacids
  作者：A.Richard Chamberlin、Milana Dezube、Patrick Dussault

  DOI：10.1016/s0040-4039(01)82994-4

  日期：1981.1
• Concise Syntheses of Natural .gamma.-Butyrolactones, (+)-trans-Whisky Lactone, (+)-trans-Cognac Lactone, (-)-Methylenolactocin, (+)-Nephrosteranic Acid, and (+)-Roccellaric Acid Using Novel Chiral Butenolide Synthons
  作者：Hiroki Takahata、Yasuhiro Uchida、Takefumi Momose

  DOI：10.1021/jo00122a051

  日期：1995.9

  cis-4-Hydroxy-5-(iodomethyl)-4,5-dihydro-2(3H)-furanones (1 and ent-1) were converted by cross-coupling with several Grignard-derived cuprates followed by benzoylation and base-induced elimination into new chiral butenolides 12, 14, ent-14, 20, and 27. The sequential conjugate addition-quenching of these butenolides under complete stereocontrol provided several polysubstituted gamma-butyrolactones including flavor components [(+)-trans-whisky lactone (3) and (+)-trans-cognac lactone (4)], the antitumor antibiotic lactone (-)-methylenolactocin (5), and lichen components [(+)-nephrosteranic acid (7) and (+)-roccellaric acid (8)].
• Stereoselective methylation of β-hydroxylactone dianions
  作者：A.Richard Chamberlin、Milana Dezube

  DOI：10.1016/s0040-4039(00)87531-0

  日期：1982.1
• CHAMBERLIN, A. R.;DEZUBE, M.;DUSSAULT, P., TETRAHEDRON LETT., 1981, 22, N 46, 4611-4614
  作者：CHAMBERLIN, A. R.、DEZUBE, M.、DUSSAULT, P.

  DOI：——

  日期：——