(S)-3-[(R)-bromo(phenyl)methyl]-1,3-dihydro-2-benzofuran-1-one | 1354005-01-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (S)-3-[(R)-bromo(phenyl)methyl]-1,3-dihydro-2-benzofuran-1-one
• 英文别名: (S)-3-[(R)-bromo(phenyl)methyl]isobenzofuran-1(3H)-one；(R)-3-[(S)-bromo(phenyl)methyl]isobenzofuran-1(3H)-one；(3S)-3-[(R)-bromo(phenyl)methyl]-3H-2-benzofuran-1-one
• CAS: 1354005-01-8
• 化学式: C₁₅H₁₁BrO₂
• 分子量: 303.155
• InChiKey: YAJWPQZVTMOWLU-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  (E)-2-styrylbenzoic acid 在 N-溴代丁二酰亚胺(NBS) 、 三苯基瞵硫 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (S)-3-[(R)-bromo(phenyl)methyl]-1,3-dihydro-2-benzofuran-1-one 、 (3R*,4S*)-4-bromo-3-phenylisochroman-1-one
  参考文献：
  名称：

  An Enantioselective Approach toward 3,4-Dihydroisocoumarin through the Bromocyclization of Styrene-type Carboxylic Acids

  摘要：

  A facile and enantioselective approach toward 3,4-dihydroisocoumarin was developed. The method involved an amino-thiocarbamate catalyzed enantioselective bromocyclization of styrene-type carboxylic acids, yielding 3-bromo-3,4-dihydroisocoumarins with good yields and ee's. 3-Bromo-3,4-dihydroisocoumarins are versatile building blocks for various dihydroisocoumarin derivatives in which the Br group can readily be modified to achieve biologically important 4-O-type and 4-N-type 3,4-dihydroisocoumarin systems. In addition, studies indicated that, by refining some parameters, the synthetically useful 5-exo phthalide products could be achieved with good yields and ee's.

  DOI：

  10.1021/jo202221c

文献信息

• Catalyst-Controlled Regio- and Stereoselective Bromolactonization with Chiral Bifunctional Sulfides
  作者：Ayano Tsuchihashi、Seiji Shirakawa

  DOI：10.1055/s-0037-1610716

  日期：2019.9

  Highly regioselective 5-exo bromolactonizations of stilbene-type carboxylic acids bearing electron-withdrawing substituents are achieved for the first time via the use of chiral bifunctional sulfide catalysts possessing a urea moiety. The chiral phthalide products are obtained in moderate to good enantioselectivities as the result of 5-exo cyclizations.

  通过使用具有尿素部分的手性双功能硫化物催化剂，首次实现了具有吸电子取代基的二苯乙烯型羧酸的高度区域选择性 5-外溴内酯化。作为 5-exo 环化的结果，手性苯酞产物以中等至良好的对映选择性获得。
• Trifluoroacetic acid catalyzed highly regioselective bromocyclization of styrene-type carboxylic acid
  作者：Tao Chen、Ying-Yeung Yeung

  DOI：10.1039/c6ob00756b

  日期：——

  A trifluoroacetic acid catalyzed highly 6-endo regioselective bromocyclization of styrene-type carboxylic acid has been developed. The resulting 3,4-dihydroisocoumarines are valuable building blocks in organic synthesis.

  已经开发了三氟乙酸催化苯乙烯型羧酸的高度6-内位区域选择性溴环化。所得的3,4-二氢异香豆素是有机合成中的重要组成部分。
• 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。