6-bromohexahydrocyclopenta[b]furan-2-one | 904891-50-5

• 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: 6-bromohexahydrocyclopenta[b]furan-2-one
• 英文别名: rel-(3aR,6S,6aS)-6-Bromohexahydro-2H-cyclopenta[b]furan-2-one；(3aR,6S,6aS)-6-bromo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• CAS: 904891-50-5
• 化学式: C₇H₉BrO₂
• 分子量: 205.051
• InChiKey: DHQQTUQHDOPHKE-ZDLURKLDSA-N

物化性质

• 沸点：
  324.2±25.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-环戊烯基-1-乙酸 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氘代氯仿 为溶剂， 反应 0.5h， 以91%的产率得到6-bromohexahydrocyclopenta[b]furan-2-one
  参考文献：
  名称：

  Ortho-substituted iodobenzenes as novel organocatalysts for bromination of alkenes

  摘要：

  合适的位向取代碘苯作为有机催化剂，通过溴碘烷的中间体，将电亲元素溴从N-溴代苏氨酸酰亚胺转移到烯烃上。

  DOI：

  10.1039/b604130b

文献信息

• Amidines as potent nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
  作者：Simon M. Ahmad、D. Christopher Braddock、Gemma Cansell、Stephen A. Hermitage、Joanna M. Redmond、Andrew J.P. White

  DOI：10.1016/j.tetlet.2007.06.112

  日期：2007.8

  (+/-)-iso-Amarine is a potent organocatalyst at 1 mol% loading for both the bromoacetoxylation of alkenes with added acetic acid and bromolactonisation of unsaturated carboxylic acids with stoichiometric NBS as the electrophilic bromine source. A simple bromoamidine with an N-Br bond has been characterised crystallographically for the first time. Asymmetric induction in the bromination reactions with enantiopure amidines was zero. (c) 2007 Elsevier Ltd. All rights reserved.

  “(+/-)-iso-Amine是一种在1 mol%负载下对烯烃的溴代乙酰氧基化反应（使用乙酸作为添加剂）以及不饱和羧酸的溴酯化反应（使用当量的NBS作为亲电溴源）的高效有机催化剂。首次通过晶体学方法表征了一种简单的具有N-Br键的溴代脒结构。使用对映体纯的脒类催化剂的溴化反应中，不对称诱导效应为零。©2007 Elsevier Ltd. 保留所有权利。”
• Novel catalytic bromolactonization of alkenoic acids using iodobenzene and Oxone®
  作者：Yan He、Ye Pu、Bo Shao、Jie Yan

  DOI：10.1002/jhet.617

  日期：2011.5

  The novel catalytic reaction for bromolactonization of alkenoic acids is reported. When iodobenzene is used as recyclable catalyst in combination with Oxone® as terminal oxidant, the cyclization of various 4‐pentenoic acids with sodium bromide is easily carried out in CF3CH2OH at room temperature and giving five‐membered bromolactones in good yields. J. Heterocyclic Chem., 2011.

  报道了用于烯酸的溴内酯化的新型催化反应。当碘代苯与Oxone®作为末端氧化剂一起用作可循环使用的催化剂时，在室温下于CF 3 CH 2 OH中可以轻松地将各种4-戊烯酸与溴化钠进行环化，并以高收率得到五元溴内酯。J.杂环化​​学.2011。
• Catalytic asymmetric bromolactonization reactions using (DHQD)2PHAL-benzoic acid combinations
  作者：Alan Armstrong、D. Christopher Braddock、Alexander X. Jones、Stacy Clark

  DOI：10.1016/j.tetlet.2013.10.043

  日期：2013.12

  Catalytic (DHQD)2PHAL as modified by added benzoic acid, is an off-the-shelf catalyst-additive combination for effecting catalytic asymmetric bromolactonization reactions. This combination delivers bromolactones with asymmetric induction at a comparable level to bespoke catalysts previously optimized for particular substrate classes.

  由添加的苯甲酸改性的催化（DHQD）2 PHAL是用于实现催化不对称溴化反应的现成催化剂-添加剂组合。这种组合可提供与以前为特定底物类型优化的定制催化剂相当的不对称诱导溴内酯。
• Study on the Bromolactonisation of Alkenoic Acids with (Diacetoxyiodo)Benzene
  作者：Yan He、Zhenping Yang、Jie Yan

  DOI：10.3184/030823410x12682297999384

  日期：2010.3

  A study on the bromolactonisation of alkenoic acids is reported. When various pent-4-enoic acids reacted with (diacetoxyiodo)benzene (DIB) and lithium bromide in CH3OH at room temperature, most of the five-membered bromolactones were obtained in good to excellent yields in short times. Some had two diastereoisomers. When but-3-enoic acid and trans-hex-3-enoic acid were treated under the same conditions

  报道了关于烯酸的溴内酯化的研究。当各种戊 4-烯酸与（二乙酰氧基碘）苯 (DIB) 和溴化锂在 CH3OH 中在室温下反应时，大多数五元溴内酯在短时间内以良好到极好的收率获得。有些具有两种非对映异构体。当丁-3-烯酸和反式-己-3-烯酸在相同条件下处理时，后处理后仅发现不饱和内酯。然而，当 6-5-烯酸处于相同条件时，目标六元溴内酯未能成功分离。
• Dimethylformamide, dimethylacetamide and tetramethylguanidine as nucleophilic organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes
  作者：Simon M. Ahmad、D. Christopher Braddock、Gemma Cansell、Stephen A. Hermitage

  DOI：10.1016/j.tetlet.2006.12.042

  日期：2007.2

  Dimethylformamide, dimethylacetamide and tetramethylguanidine were found to act as increasingly active catalysts for the bromolactonisation of gamma,delta- and delta,epsilon-unsaturated carboxylic acids with N-bromosuccinimide. The catalysts are readily removed in the work-up by washing with water to provide the pure bromolactone products without the need for column chromatography. Catalysis of the intermolecular bromoacetoxylation of alkenes with acetic acid and NBS by TMG was also demonstrated. (c) 2006 Elsevier Ltd. All rights reserved.