(E)-(3-(methylsulfonyl)prop-1-en-1-yl)benzene | 16215-16-0

• 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: (E)-(3-(methylsulfonyl)prop-1-en-1-yl)benzene
• 英文别名: [(E)-3-methylsulfonylprop-1-enyl]benzene
• CAS: 16215-16-0
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: FLZFIKYBSDONQJ-VMPITWQZSA-N

物化性质

• 沸点：
  391.3±31.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 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

• 作为产物：
  描述：

  E-(3-phenylallyl) methyl sulfide 在 双氧水 、 溶剂黄146 作用下， 生成 (E)-(3-(methylsulfonyl)prop-1-en-1-yl)benzene
  参考文献：
  名称：

  Baliah; Shanmuganathan, Journal of the Indian Chemical Society, 1958, vol. 35, p. 31,34

  摘要：

  DOI：

文献信息

• Direct Substitution of Primary Allylic Amines with Sulfinate Salts
  作者：Xue-Song Wu、Yan Chen、Man-Bo Li、Meng-Guang Zhou、Shi-Kai Tian

  DOI：10.1021/ja306407x

  日期：2012.9.12

  primary allylic amines was substituted directly by sulfinate salts with excellent regio- and stereoselectivities. In the presence of 0.1 mol % [Pd(allyl)Cl](2), 0.4 mol % 1,4-bis(diphenylphosphino)butane (dppb), and excess boric acid, a range of α-unbranched primary allylic amines were smoothly substituted with sodium sulfinates in an α-selective fashion to give structurally diverse allylic sulfones

  主要烯丙基胺中的 NH(2) 组被亚磺酸盐直接取代，具有出色的区域和立体选择性。在 0.1 mol % [Pd(allyl)Cl](2)、0.4 mol % 1,4-双（二苯基膦基）丁烷 (dppb) 和过量硼酸的存在下，一系列 α-无支链伯烯丙胺被顺利合成以α-选择性方式用亚磺酸钠取代，得到结构多样的烯丙基砜，收率良好，具有独特的 E 选择性。用 1,1'-bi-2-naphthol (BINOL) 代替 dppb 可以将不对称的 α-手性伯烯丙胺转化为相应的烯丙基砜，收率良好至极好，同时具有极好的 ee 保留率。重要的，
• Reciprocal-Activation Strategy for Allylic Sulfination with Unactivated Allylic Alcohols
  作者：Peizhong Xie、Zuolian Sun、Shuangshuang Li、Xinying Cai、Ju Qiu、Weishan Fu、Cuiqing Gao、Shisheng Wu、Xiaobo Yang、Teck-Peng Loh

  DOI：10.1021/acs.orglett.0c01747

  日期：2020.6.19

  A reciprocal-activation strategy for allylic sulfination with unactivated allylic alcohols was developed. In this reaction, the hydrogen bond interaction between allylic alcohols and sulfinic acids allowed for reciprocal activation, which enabled a dehydrative cross-coupling process to occur under mild reaction conditions. This reaction worked in an environmentally friendly manner, yielding water as

  已开发了一种与未活化的烯丙醇进行烯丙基硫化的相互活化策略。在该反应中，烯丙醇和亚磺酸之间的氢键相互作用使得相互活化，这使得在温和的反应条件下发生脱水交叉偶联过程。该反应以对环境友好的方式进行，产生水作为唯一的副产物。可以以良好的收率和优异的收率获得各种烯丙基砜，并且具有宽泛的官能团耐受性。在克级反应中，可以通过过滤方便地以高收率分离烯丙基砜。
• Novel Model Sulfur Compounds as Mechanistic Probes for Enzymatic and Biomimetic Oxidations
  作者：Alicia B. Peñéñory、Juan E. Argüello、Marcelo Puiatti

  DOI：10.1002/ejoc.200400382

  日期：2005.1

  is proposed that the mechanism of the biomimetic sulfoxidations of sulfides 1c and 2−5 by TPPFeIIICl is direct oxygen transfer. Three enzymes − Coprinus cinereus peroxidase (CiP), horseradish peroxidase (HRP) and chloroperoxidase (CPO) − were studied in the oxidation of sulfides 1a, 2, 4 and 5. The use of a racemic alkyl hydroperoxide in the CiP enzymatic oxidation of sulfides 5 and 2 yielded the corresponding

  为了测试硫化物自由基阳离子在仿生和酶促氧化中的中介作用，硫化物 PhSCH3 (1a)、PhSCH2Ph (1b)、PhSCHPh2 (1c)、PhSCPh3 (1d)、CH3SCHPh2 (2)、PhSCH2CH=CH2 (3)、PhSCH2CH =CHPh (4) 和 CH3SCH2CH=CHPh (5) 进行了研究，并将它们的结果与相应的化学电子转移 (CET) 和光致电子转移 (PET) 氧化所获得的结果进行了比较。在硝酸铈 (IV) 铵 (CAN) 存在下，CET 从 3-5 生成的自由基阳离子仅产生烷基阳离子和硫基自由基 (RS·) 的裂解产物，而 2·+ 提供了裂解产物，主要是 α -去质子化产品。硫化物 1a 和 1b 用 C(NO2)4 光化学处理只得到相应的亚砜，而裂解是 1c、2 和 5 光反应的主要途径，对于 1d，仅观察到后一个过程。这些结果支持我们选择硫化物 RSCHPh2、RSCH2CH=CHPh
• An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity
  作者：Gollapudi RAVI KUMAR、Chandra Rao DASIREDDY、Ravi VARALA、Vijay KOTRA、Hari Babu BOLLIKOLLA

  DOI：10.3906/kim-2003-10

  日期：——

  A series of nine methyl sulphones (3a–3i) starting from the aldehydes (1a–1i) were synthesized in two consecutive steps. In the first step, preparation of allyl alcohols (2a–2i) from their corresponding aldehydes by the reaction of sodium borohydride in methanol at room temperature is reported. Finally, methyl sulphones are synthesized by condensing sodium methyl sulfinates with allyl alcohols in the presence of BF3.Et2O in acetic acid medium at room temperature for about 2–3 h. The reaction conditions are simple, yields are high (85%–95%), and the products were obtained with good purity. All the synthesized compounds were characterized by their 1H, 13C NMR, and mass spectral analysis. All the title compounds were screened for antimicrobial activity. Among the compounds tested, the compound 3f has inhibited both Gram positive and Gram negative bacteria effectively and compound 3i has shown potent antifungal activity. These promising components may help to develop more potent drugs in the near future for the treatment of bacterial and fungal infections.

  以醛（1a-1i）为起点，通过两个连续步骤合成了一系列九种甲基砜（3a-3i）。第一步，在室温下通过硼氢化钠在甲醇中的反应从相应的醛制备烯丙基醇（2a-2i）。最后，在醋酸介质中，BF3.Et2O 存在下，室温下冷凝甲基亚磺酸钠与烯丙基醇，约 2-3 小时，合成甲基砜。反应条件简单，收率高（85%-95%），产物纯度好。所有合成化合物均通过 1H、13C NMR 和质谱分析进行了表征。对所有标题化合物进行了抗菌活性筛选。在测试的化合物中，化合物 3f 对革兰氏阳性菌和革兰氏阴性菌都有有效的抑制作用，而化合物 3i 则显示出强大的抗真菌活性。这些有前景的成分可能有助于在不久的将来开发出更多治疗细菌和真菌感染的特效药物。
• Allylsulfones through Palladium‐Catalyzed Allylic C−H Sulfonylation of Terminal Alkenes
  作者：Tingting Chen、Jassmin Lahbi、Gianluigi Broggini、Alexandre Pradal、Giovanni Poli

  DOI：10.1002/ejoc.202201493

  日期：2023.2.17

  distinct protocols for the preparation of allylsulfones via Pd(II)-catalyzed allylic C−H activation. While the former protocol consists of a direct Pd(II)-catalyzed oxidative C−H allylic sulfonylation in the presence of sulfinate anions, the latter involves a sequential one-pot Pd(II)-catalyzed C−H allylic acetoxylation followed by a Pd(0)-catalyzed sulfonylation.

  我们报告了两种不同的方案，用于通过 Pd(II) 催化的烯丙基 C−H 活化制备烯丙基砜。前者方案包括在亚磺酸盐阴离子存在下直接 Pd(II) 催化的氧化 C−H 烯丙基磺酰化，而后者涉及连续的一锅 Pd(II) 催化的 C−H 烯丙基乙酰氧基化，然后是 Pd (0)-催化磺酰化。