2,2-Bis(phenylsulfonyl)-1-(2'-furyl)ethene | 40978-76-5

• 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: 2,2-Bis(phenylsulfonyl)-1-(2'-furyl)ethene
• 英文别名: Furfuryliden-α,α-(bis-phenylsulfonyl)-methan；2-(2,2-bis(phenylsulfonyl)vinyl)furan；1,1-bis-benzenesulfonyl-2-furan-2-yl-ethene；2-[2,2-Bis(benzenesulfonyl)ethenyl]furan
• CAS: 40978-76-5
• 化学式: C₁₈H₁₄O₅S₂
• 分子量: 374.438
• InChiKey: PCYDGDVLPZTWMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-Bis(phenylsulfonyl)-1-(2'-furyl)ethene 在 过氧化氢苯甲酰 、 四丁基硫酸氢铵 sodium hydroxide 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 、 sodium amalgam 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 21.0h， 生成 4,5-Diethyl-6-methyl-3-<3-(2'-furyl)propyl>-2H-pyran-2-one
  参考文献：
  名称：

  Intramolecular [4 + 3]-cycloadditions of photochemically generated oxyallyl zwitterions: a route to functionalized cyclooctanoid skeletons

  摘要：

  [4 + 3]-Cycloaddition of photochemically generated, 4-pyrone derived oxyallyl zwitterions and furans was examined as a potential approach to keto-bridged cyclooctenes. In one case, intermolecular cycloaddition proceeded to give adduct 3 with complete diastereoselectivity and in moderate yield, but the reaction was not general. Substrates 5a-i were then prepared in one to three steps from either 3-methyl-4H-pyran-4-ones or 3-hydroxy-2-methyl-4H-pyran-4-one, and their viability in intramolecular [4 + 3]-cycloadditions was examined. Substrates 5a-e, in which the tether was attached to the incipient zwitterion via a carbon, underwent cycloaddition to give [4 + 3]-cycloadducts 7 and 8 in varying yields, along with small amounts of cage compound 9. In contrast, 5f-i, in which the tether was attached to the incipient zwitterion via an oxygen, gave only solvent-trapping products 10. In one case (5e), isomeric pyran-2-ones 11e/12e were produced in addition to [4+3]-cycloadduct 8e and cage compound 9e. Moreover, it was found that 11e and 12e both underwent subsequent photochemical crossed [4 + 4]-cycloadditions to give lactone-bridged cyclooctadienes 13e and 14e. The structures of 11e/12e and their [4 + 4]-cycloadducts were confirmed by synthesis of each of the 2-pyrones via alternative routes.

  DOI：

  10.1021/jo00076a047
• 作为产物：
  描述：

  糠醛 、 双苯磺酸甲烷 以 甲醇 为溶剂， 生成 2,2-Bis(phenylsulfonyl)-1-(2'-furyl)ethene
  参考文献：
  名称：

  Intramolecular [4 + 3]-cycloadditions of photochemically generated oxyallyl zwitterions: a route to functionalized cyclooctanoid skeletons

  摘要：

  [4 + 3]-Cycloaddition of photochemically generated, 4-pyrone derived oxyallyl zwitterions and furans was examined as a potential approach to keto-bridged cyclooctenes. In one case, intermolecular cycloaddition proceeded to give adduct 3 with complete diastereoselectivity and in moderate yield, but the reaction was not general. Substrates 5a-i were then prepared in one to three steps from either 3-methyl-4H-pyran-4-ones or 3-hydroxy-2-methyl-4H-pyran-4-one, and their viability in intramolecular [4 + 3]-cycloadditions was examined. Substrates 5a-e, in which the tether was attached to the incipient zwitterion via a carbon, underwent cycloaddition to give [4 + 3]-cycloadducts 7 and 8 in varying yields, along with small amounts of cage compound 9. In contrast, 5f-i, in which the tether was attached to the incipient zwitterion via an oxygen, gave only solvent-trapping products 10. In one case (5e), isomeric pyran-2-ones 11e/12e were produced in addition to [4+3]-cycloadduct 8e and cage compound 9e. Moreover, it was found that 11e and 12e both underwent subsequent photochemical crossed [4 + 4]-cycloadditions to give lactone-bridged cyclooctadienes 13e and 14e. The structures of 11e/12e and their [4 + 4]-cycloadducts were confirmed by synthesis of each of the 2-pyrones via alternative routes.

  DOI：

  10.1021/jo00076a047

文献信息

• Enantiocontrolled Synthesis of β‐Branched α‐Amino Acids by Using Cu ^I ‐Catalyzed 1,4‐Addition of Glycine Imines to β‐Substituted <i>gem</i> ‐Diactivated Olefins
  作者：Jorge Hernández‐Toribio、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1002/chem.201100374

  日期：2011.5.27

  Branching out! The catalytic asymmetric conjugate addition of glycinate Schiff bases to β‐substituted gem‐diactivated Michael acceptors under proton transfer conditions gives a variety of β‐branched α‐amino acids (see scheme; Dpm=diphenylmethylene, EWG=electron‐withdrawing group) with excellent levels of diastereo‐ (typically syn/anti >90:10) and enantiocontrol (90–99 % ee).

  分支出！催化不对称共轭加成的甘氨酸Schiff碱至β -取代的宝石-diactivated质子转移条件下迈克尔受体给出的各种β-α支链氨基酸（参见方案; DPM =二苯基亚甲基，EWG =吸电子基团）具有优良的非对映体水平（通常是syn / anti > 90:10）和对映体控制（90–99％  ee）。
• Organocatalytic Michael Addition of Aldehydes to Vinyl Sulfones: Enantioselective α-Alkylations of Aldehydes and Their Derivatives
  作者：Qiang Zhu、Yixin Lu

  DOI：10.1021/ol8019296

  日期：2008.11.6

  Organocatalytic asymmetric Michael reaction of unmodified aldehydes to vinyl sulfones catalyzed by silylated biarylprolinol afforded the desired Michael products with exceptional enantioselectivity. The described enantioselective addition to vinyl sulfones, in combination with desulfonation, offers a unique, asymmetric entry to alpha-alkylated aldehydes and their derivatives.

  甲硅烷基化的联芳基脯氨醇催化的未修饰醛与乙烯基砜的有机催化不对称迈克尔反应提供了所需的迈克尔产物，且具有出色的对映选择性。所述的乙烯基砜的对映选择性加成与脱硫结合提供了α-烷基化醛及其衍生物的独特，不对称入口。
• ZIEGLER E.; RUEF W.; ZWAINZ J. G., Z. NATURFORSCH. <ZENB-AX>, 1975, 30B, NO 9-10, 755-759
  作者：ZIEGLER E.、 RUEF W.、 ZWAINZ J. G.

  DOI：——

  日期：——
• Intramolecular [4 + 3]-cycloadditions of photochemically generated oxyallyl zwitterions: a route to functionalized cyclooctanoid skeletons
  作者：F. G. West、Claudia Hartke-Karger、Daniel J. Koch、Cynthia E. Kuehn、A. M. Arif

  DOI：10.1021/jo00076a047

  日期：1993.11

  [4 + 3]-Cycloaddition of photochemically generated, 4-pyrone derived oxyallyl zwitterions and furans was examined as a potential approach to keto-bridged cyclooctenes. In one case, intermolecular cycloaddition proceeded to give adduct 3 with complete diastereoselectivity and in moderate yield, but the reaction was not general. Substrates 5a-i were then prepared in one to three steps from either 3-methyl-4H-pyran-4-ones or 3-hydroxy-2-methyl-4H-pyran-4-one, and their viability in intramolecular [4 + 3]-cycloadditions was examined. Substrates 5a-e, in which the tether was attached to the incipient zwitterion via a carbon, underwent cycloaddition to give [4 + 3]-cycloadducts 7 and 8 in varying yields, along with small amounts of cage compound 9. In contrast, 5f-i, in which the tether was attached to the incipient zwitterion via an oxygen, gave only solvent-trapping products 10. In one case (5e), isomeric pyran-2-ones 11e/12e were produced in addition to [4+3]-cycloadduct 8e and cage compound 9e. Moreover, it was found that 11e and 12e both underwent subsequent photochemical crossed [4 + 4]-cycloadditions to give lactone-bridged cyclooctadienes 13e and 14e. The structures of 11e/12e and their [4 + 4]-cycloadducts were confirmed by synthesis of each of the 2-pyrones via alternative routes.