(5R)-5-丁-3-烯-1-基二氢呋喃-2(3H)-酮 | 110793-80-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: (5R)-5-丁-3-烯-1-基二氢呋喃-2(3H)-酮
• 英文名称: (R)-5-(But-3-en-1-yl)dihydrofuran-2(3H)-one
• 英文别名: (5R)-5-but-3-enyloxolan-2-one
• CAS: 110793-80-1
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: BUGGYMCPMUQOPG-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R)-5-丁-3-烯-1-基二氢呋喃-2(3H)-酮 在 钯 氢气 作用下， 生成 (R)-5-正丁基二氢呋喃-2-酮
  参考文献：
  名称：

  某些寄生性黄蜂中卤素腺内酯的合成和绝对立体化学（膜翅目：:科）

  摘要：

  有效的合成和对映选择性气相色谱法已经证实了结构，并建立了寄生蜂（膜翅目：:科）中某些新型双环内酯（四氢呋喃呋喃酮）的绝对立体化学。共生的γ-内酯，辛酸-4-内酯和十二烷-4-内酯具有（R）-构型。

  DOI：

  10.1016/s0040-4039(97)00661-8
• 作为产物：
  描述：

  1,2-环氧基-5-己烯 在 (-)-chloro((1R,2R)-4,4',6,6'-tetra-tert-butyl-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato)manganese(III) 、 magnesium(II) chloride hexahydrate 、 sodium ethanolate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5R)-5-丁-3-烯-1-基二氢呋喃-2(3H)-酮
  参考文献：
  名称：

  Process Development of Halaven®: Synthesis of the C14-C35 Fragment via Iterative Nozaki-Hiyama-Kishi Reaction-Williamson Ether Cyclization

  摘要：

  Multikilogram manufacturing process of the Halaven (R) C14-C35 fragment is described. The synthesis features convergent assembly of subunits by iterative asymmetric Ni/Cr-mediated coupling executed in fixed equipment.

  DOI：

  10.1055/s-0032-1317920

文献信息

• [EN] INTERMEDIATES FOR THE PREPARATION OF HALICHONDRIN B<br/>[FR] INTERMEDIAIRES POUR LA PREPARATION D'HALICHONDRINE B
  申请人：EISAI CO LTD

  公开号：WO2005118565A1

  公开（公告）日：2005-12-15

  The present invention provides macrocyclic compounds, synthesis of the same and intermediates thereto. Such compounds, and compositions thereof, are useful for treating or preventing proliferative disorders Formula (F-4).

  本发明提供大环化合物，其合成以及中间体。这些化合物及其组合物对于治疗或预防增殖性疾病（F-4式）是有用的。
• 1,3-Asymmetric induction in the intramolecular [2+2] cycloaddition of alkene-keteniminium salts. Synthesis of (+)-gibberellic acid key intermediate
  作者：Pil-Jong Shim、Hee-Doo Kim

  DOI：10.1016/s0040-4039(98)02228-x

  日期：1998.12

  Optically active bicyclo[4.2.0]octan-7-ones were synthesized by stereoselective intramolecular [2+2] cycloaddition of alkene-keteniminium salt derived from L-glutamic acid, based on 1,3-asymmetric induction. Synthetic application toward (+)-gibberellic acid key intermediate was also described.

  光学活性的双环[4.2.0] octan-7-ones是通过立体选择性的分子内[2 + 2]环加成衍生自L-谷氨酸的烯烃-酮亚胺盐，基于1,3-不对称诱导而合成的。还描述了对（+）-赤霉素关键中间体的合成应用。
• INTERMEDIATES FOR THE PREPARATION OF ANALOGS OF HALICHONDRIN B
  申请人：Eisai R&D Management Co., Ltd.

  公开号：US20140163242A1

  公开（公告）日：2014-06-12

  Intermediates and methods of their use in the synthesis of analogs of halichondrin B are provided.

  提供了中间体及其在合成半乳霉素B类似物中的使用方法。
• Intermediates for the Preparation of Halichondrin B
  申请人：Austad Brian

  公开号：US20070244187A1

  公开（公告）日：2007-10-18

  The present invention provides macrocyclic compounds, synthesis of the same and intermediates thereto. Such compounds, and compositions thereof, are useful for treating or preventing proliferative disorders Formula (F-4).

  本发明提供了大环化合物、其合成方法和中间体。这些化合物及其组合物可用于治疗或预防增生性疾病。化学式如下（F-4）。
• A Direct Method for the Conversion of Terminal Epoxides into γ-Butanolides
  作者：Mohammad Movassaghi、Eric N. Jacobsen

  DOI：10.1021/ja025604c

  日期：2002.3.1

  A new and efficient process for the conversion of terminal epoxides to gamma-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine and boron trifluoride diethyl etherate in dichloromethane at 0 degrees C rapidly affords a cyclic keteneaminal that can be hydrolyzed and protodesilylated under mild conditions to provide the corresponding gamma-butanolide in high yield. The net transformation is equivalent to an acetate enolate opening of terminal epoxides. The formation of a cyclic keteneaminal as the direct addition product was observed by monitoring of the reaction by IR and NMR spectroscopy. Functionalized gamma-lactones were prepared by the interception of the reactive cyclic keteneaminal prior to hydrolysis. Reactions with enantiomerically enriched terminal epoxides provide the corresponding gamma-butanolides without loss of optical activity. The compatibility of the present methodology with a wide range of functional groups is noteworthy.