3-叔丁氧基甲基-4-氟-3-羟基丁酸叔丁酯 | 916069-73-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 3-叔丁氧基甲基-4-氟-3-羟基丁酸叔丁酯
• 英文名称: 3-tert-butoxymethyl-4-fluoro-3-hydroxybutyric acid tert-butyl ester
• 英文别名: tert-butyl 3-(fluoromethyl)-3-hydroxy-4-[(2-methylpropan-2-yl)oxy]butanoate
• CAS: 916069-73-3
• 化学式: C₁₃H₂₅FO₄
• 分子量: 264.338
• InChiKey: DRAWEGQBRUGFGE-UHFFFAOYSA-N

物化性质

• 沸点：
  331.9±42.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-叔丁氧基甲基-4-氟-3-羟基丁酸叔丁酯 在 [Ru(OAc)2((R)-3,5-t-Bu-MeOBIPHEP)] 、 硫酸 、 氢气 、 乙酸酐 、 三乙胺 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， -10.0~60.0 ℃ 、1.5 MPa 条件下， 反应 31.5h， 生成 (S)-4-fluoromethyldihydro-3H-furan-2-one
  参考文献：
  名称：

  Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety

  摘要：

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.

  DOI：

  10.1021/op200019k
• 作为产物：
  描述：

  叔丁基缩水甘油醚 在 氟化氢二聚体阴离子 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 三乙二醇 为溶剂， 反应 8.0h， 生成 3-叔丁氧基甲基-4-氟-3-羟基丁酸叔丁酯
  参考文献：
  名称：

  Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety

  摘要：

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.

  DOI：

  10.1021/op200019k

文献信息

• Process for the preparation of (S)-4-fluoromethyl-dihydro-furan-2-one useful in the preparation of the DPP-IV inhibitor (S)-1 ((2S,3S,11bS)-2-amino-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2h-pyrido[2,1-a] isoquinolin-3-yl)-4-fluoromethyl-pyrrolidin-2-one
  申请人：Abrecht Stefan

  公开号：US20060270853A1

  公开（公告）日：2006-11-30

  This invention relates to a process of the preparation of the novel intermediate (S)-4-fluoromethyl-dihydro-furan-2-one of the formula and with its use for the manufacture of pyrido[2,1-a]isoquinoline derivatives of the formula which are useful for the treatment and/or prophylaxis of diseases which are associated with DPP IV.

  本发明涉及制备新中间体(S)-4-氟甲基-二氢呋喃-2-酮的方法，其化学式为：并利用该中间体制备式为：的吡啶[2,1-a]异喹啉衍生物，这些衍生物对于治疗和/或预防与DPP IV相关的疾病是有用的。
• Process for the preparation of (S)-4-fluoromethyl-dihydro-furan-2-one useful in the preparation of the DPP-IV inhibitor (S)-1 ((2S,3S,11bS)-2-amino-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2H-pyrido[2,1-a] isoquinolin-3-yl)-4-fluoromethyl-pyrrolidin-2-one
  申请人：Hoffman-La Roche Inc.

  公开号：US07619101B2

  公开（公告）日：2009-11-17

  This invention relates to a process of the preparation of the novel intermediate (S)-4-fluoromethyl-dihydro-furan-2-one of the formula and with its use for the manufacture of pyrido[2,1-a]isoquinoline derivatives of the formula which are useful for the treatment and/or prophylaxis of diseases which are associated with DPP IV.

  本发明涉及一种制备新型中间体(S)-4-氟甲基二氢呋喃-2-酮的方法，并利用其制造式为的吡啶并[2,1-a]异喹啉衍生物，用于治疗和/或预防与DPP IV相关的疾病。
• PREPARATION OF (S)-4-FLUOROMETHYL-DIHYDRO-FURAN-2-ONE
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1893595B1

  公开（公告）日：2008-09-03
• US7619101B2
  申请人：——

  公开号：US7619101B2

  公开（公告）日：2009-11-17
• [EN] PREPARATION OF (S)-4-FLUOROMETHYL-DIHYDRO-FURAN-2-ONE<br/>[FR] PRÉPARATION DE (S)-4-FLUOROMÉTHYL-DIHYDRO-FURAN-2-ONE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2006125728A1

  公开（公告）日：2006-11-30

  [EN] This invention relates to a process of the preparation of the novel intermediate (S)-4-fluoromethyl-dihydro-furan-2-one of the formula (I) and with its use for the manufacture of pyrido[2,1-a] isoquinoline derivatives of the formula (II) which are useful for the treatment and / or prophylaxis of diseases which are associated with DPP IV.
  [FR] Procédé de préparation du nouvel intermédiaire (S)-4-fluorométhyl-dihydro-furan-2-one de formule (I) et utilisation dudit intermédiaire pour la production de dérivés de pyrido[2,1-a]isoquinoline de formule (II) qui sont utiles pour le traitement et / ou la prophylaxie de maladies associées à DPP IV.