2-(bromomethyl)-3-(phenylsulfonyl)-1-propene | 129800-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(bromomethyl)-3-(phenylsulfonyl)-1-propene
• 英文别名: 2-(bromomethyl)-2-propenyl phenyl sulfone；(2-bromomethyl-prop-2-ene-1-sulfonyl)-benzene；Benzene, [[2-(bromomethyl)-2-propenyl]sulfonyl]-；2-(bromomethyl)prop-2-enylsulfonylbenzene
• CAS: 129800-98-2
• 化学式: C₁₀H₁₁BrO₂S
• 分子量: 275.166
• InChiKey: WBSHCYNWADKVBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(bromomethyl)-3-(phenylsulfonyl)-1-propene 在 barium dihydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (1E,3E)-1-benzenesulfonyl-2-methyl-4-phenylbuta-1,3-diene
  参考文献：
  名称：

  γ-Allyl Phosphinoyl Phenyl Sulfone (GAPPS):  A Conjunctive Reagent for the Synthesis of EE, EZ, and ET 1,3-Dienes

  摘要：

  A three-operation conjunctive strategy is available for the synthesis of EE, EZ, and ET dienes. This protocol employs a sequential Wadsworth-Emmons reaction using a GAPPS reagent followed by alkylation of an allylic sulfone anion, and finally ligand-mediated, palladium-catalyzed desulfonylation.

  DOI：

  10.1021/ja0377596
• 作为产物：
  描述：

  1-(phenylsulfonyl)-2-methyl-2-propene 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以48%的产率得到2-(bromomethyl)-3-(phenylsulfonyl)-1-propene
  参考文献：
  名称：

  γ-Allyl Phosphinoyl Phenyl Sulfone (GAPPS):  A Conjunctive Reagent for the Synthesis of EE, EZ, and ET 1,3-Dienes

  摘要：

  A three-operation conjunctive strategy is available for the synthesis of EE, EZ, and ET dienes. This protocol employs a sequential Wadsworth-Emmons reaction using a GAPPS reagent followed by alkylation of an allylic sulfone anion, and finally ligand-mediated, palladium-catalyzed desulfonylation.

  DOI：

  10.1021/ja0377596

文献信息

• Carbocyclic HIV protease inhibitors
  申请人：Hoffmann-La Roche Inc.

  公开号：US06632826B1

  公开（公告）日：2003-10-14

  The present invention is concerned with novel HIV protease Inhibitors of formula I as individual isomers, racemates, non-racemic mixtures or mixtures of diastereoisomers; wherein n, R1 and R4 are as described herein. The compounds of formula I are peptide mimetics which act as inhibitors of the HIV aspartyl protease, an essential enzyme in the replicative life cycle of HIV.

  本发明涉及一种新型HIV蛋白酶抑制剂，其化学式为I型，可以是单体异构体、外消旋体、非外消旋混合物或二对映异构物的混合物；其中n、R1和R4如本文所述。化合物I的化学式是肽类模拟物，作为HIV天冬氨酸蛋白酶的抑制剂，这是HIV复制生命周期中不可或缺的酶。
• Michael reactions of allylic sulfones with nitroolefins. Regio- and stereochemical control
  作者：Eugene Ghera、Efrat Ben-Yaakov、Tamar Yechezkel、Alfred Hassner

  DOI：10.1016/s0040-4039(00)79071-x

  日期：1992.5

  Michael addition of allylsulfone carbanions to nitroolefins where shown to be sensitive to substitution in both the donor and the acceptor. While sulfone 10 gave predominantly products of γ-addition with aromatic nitroolefins, addition to aliphatic nitroolefins produced almost exclusively α-adducts. In the presence of an OH function in the sulfone (see 13) only (Z) γ-adducts were observed, while a

  烯丙基砜碳负离子在硝基烯烃上的迈克尔加成反应对供体和受体均表现出对取代敏感的作用。砜10主要产生与芳族硝基烯烃的γ-加成产物，而除了脂族硝基烯烃外，几乎仅产生α-加合物。在砜中存在OH功能的情况下（参见13），仅观察到（Z）γ加合物，而溴取代基则逆转了区域化学反应。
• Synthesis of chiral non-racemic 2-arylpyrrolines by a [3+2] cycloaddition route
  作者：Thiagarajan Balasubramanian、Alfred Hassner

  DOI：10.1016/0040-4039(96)01176-8

  日期：1996.8

  A new and efficient diastereoselective (upto 76% de) synthesis of 2-aryl-3-pyrroline derivatives 3a-f has been achieved by [3+2] cycloaddition of allylsulfone 1 and non-racemic sulfinimines 2. Separation of the diastereomers led to optically pure 2(R)-pyrrolines (62–72% yield). The N-sulfinyl auxiliary can be removed with TFA.

  通过[3 + 2]烯丙基砜1和非外消旋亚胺2的环加成反应，实现了2-芳基-3-吡咯啉衍生物3a-f的新的高效非对映选择性（高达76％de）合成。非对映异构体的分离导致产生光学纯的2（R）-吡咯啉（62-72％的产率）。N-亚磺酰基助剂可以用TFA除去。
• Asymmetric synthesis of substituted cyclopentanes via Michael initiated ring closure reactions
  作者：Tamar Yechezkel、Eugene Ghera、Namakkal G. Ramesh、Alfred Hassner

  DOI：10.1016/0957-4166(96)00301-1

  日期：1996.8

  Michael initiated ring closure reactions of bromosulfone 1 and γ-oxygenated (E)-α,β-unsaturated esters, which lead stereohomogeneously to trisubstituted methylenecylopentanes, proceed also with good facial selectivity. The use of nonracemic enoate 1 4 in these reactions led to the synethesis of enantiomerically pure cylcopentanone 1 7. The reason for the preferred anti-selective. Michael addition of

  Michael引发了溴砜1和γ-氧化的（E）-α，β-不饱和酯的闭环反应，这些反应立体异构地导致三取代的亚甲基环戊二烯，并且具有良好的面部选择性。在这些反应中使用非外消旋的烯酸酯1 4导致对映体纯净的环戊烷酮1 7的合成。首选抗选择性的原因。讨论了烯丙基和烷基α-苯基磺酰基锂化试剂对烯酸酯1 4的迈克尔加成反应。
• Stereoselective Addition of Sulfone Carbanions to C=N: A Critical Dependence on the Stability and Reactivity of the Amide Anions in MIRC Reactions
  作者：Alfred Hassner、Diana Usak、Ramaiah Kumareswaran、Oded Friedman

  DOI：10.1002/ejoc.200300781

  日期：2004.6

  selective synthesis of functionalized 4-methylenepyrrolidines by tuning the electron-withdrawing group (ArSO2, COOEt, ArSO) attached to the acceptor imine nitrogen atom during addition of allyl sulfone carbanions. Sulfone carbanion additions to 2H-azirines were also examined. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  通过在添加烯丙基砜碳负离子过程中调节与受体亚胺氮原子相连的吸电子基团（ArSO2、COOEt、ArSO），开发了一种选择性合成功能化 4-亚甲基吡咯烷的方法。还检查了添加到 2H-氮杂环中的砜碳负离子。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)