[3-(phenylsulfonyl)prop-1-ene-1,1-diyl]dibenzene | 21378-26-7

• 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: [3-(phenylsulfonyl)prop-1-ene-1,1-diyl]dibenzene
• 英文别名: 3,3-Diphenyl-2-propenyl-phenyl-sulfon；(3,3-Diphenyl-2-propenyl)-phenyl sulfone；[3-(benzenesulfonyl)-1-phenylprop-1-enyl]benzene
• CAS: 21378-26-7
• 化学式: C₂₁H₁₈O₂S
• 分子量: 334.439
• InChiKey: CYVRTIAJWRWZAU-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  539.3±50.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  [3-(phenylsulfonyl)prop-1-ene-1,1-diyl]dibenzene 在 碘苯二乙酸 、 硫酸 、 水 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.33h， 以83%的产率得到1,2-diphenyl-3-(phenylsulfonyl)propan-1-one
  参考文献：
  名称：

  无金属条件下烯丙醇与亚磺酸多米诺反应的一锅法合成烯丙基砜，酮砜和三氟甲苯醇

  摘要：

  通过建立芳基烯丙醇的磺酰化反应，然后由碘代苯二乙酸酯（PIDA）促进氧化功能化，建立了无金属串联程序。烯丙基砜，γ-酮砜和三氟烯丙基烯丙醇可通过一次操作构建。该方法结合了磺酰基（芳基和triflyl）功能，并具有简单的后处理步骤。

  DOI：

  10.1002/chem.201500469
• 作为产物：
  描述：

  二苯甲酮 在 tetra-N-butylammonium tribromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 [3-(phenylsulfonyl)prop-1-ene-1,1-diyl]dibenzene
  参考文献：
  名称：

  水中烯丙基砜的一锅法无金属合成

  摘要：

  提出了烯丙醇和亚磺酸钠之间的一锅脱水交叉偶联反应，该反应以良好至优异的产率提供烯丙基砜。其广泛的底物范围包括对称和不对称的α,α-二芳基和α-芳基取代的烯丙醇以及芳基和烷基亚磺酸钠。对于不对称烯丙基底物， E异构体占主导地位，并具有优异的立体选择性。对照实验为提出的自由基介导机制提供了基础。无金属工艺采用廉价且市售的三溴化四丁基铵作为催化剂，H 2 O作为溶剂。这种简单、高效、弱毒、环境友好的策略的显着特点包括温和方便的操作条件和易于获得的起始原料。

  DOI：

  10.1021/acs.joc.3c01421

文献信息

• Cyclopropanecarboxylic acids and esters
  申请人：Roussel-UCLAF

  公开号：US03997586A1

  公开（公告）日：1976-12-14

  Novel cyclopropanecarboxylic acids and esters of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are selected from the group consisting of hydrogen, alkyl, aralkyl, aryl, alkenyl non-conjugated with the cyclopropane ring, alkenyl non-conjugated with the cyclopropane ring, cycloalkyl, cycloalkenyl and heterocyclic; R is selected from the group consisting of OH and OR' in which R' is selected from the group consisting of lower alkyl which may be substituted, benzyl which may be substituted on the phenyl or methylene portion, N-methylene-dicarboximide, (5-benzyl-furyl-3) methyl, and a cyclopentene of the formula ##STR2## WHEREIN R" is selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic; A is a bivalent alkyl radical selected from the group consisting of ##STR3## WHEREIN R.sub.1 is selected from the group consisting of hydrogen and lower alkyl, R.sub.2 and R.sub.3 are selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic and taken together with the carbon atom to which they are attached form a ring selected from the group consisting of carbon homo rings and unsaturated carbon homo rings of 3 to 7 carbon atoms and heterocyclic rings which may be substituted with lower alkyl or lower alkoxy and R.sub.2 and R.sub.3 may together form a polycyclic aromatic radical, R.sub.4 is lower alkyl, R.sub.5 is selected from the group consisting of hydrogen and lower alkyl and R.sub.4 and R.sub.5 together with the carbon atoms to which they are attached may form a saturated or unsaturated carbon homo ring or a heterocyclic ring, Y is selected from the group consisting of methylene and a saturated or unsaturated carbon chain and Y' is selected from the group consisting of methine and a saturated or unsaturated carbon chain with the proviso that when Z.sub.1 and Z.sub.2 are methyl and R.sub.1 is hydrogen, R.sub.2 is other than methyl and their preparation.

  新型环丙烷羧酸及其酯类化合物，其通式为##STR1##其中Z1和Z2选自氢、烷基、芳烷基、芳基、非共轭于环丙烷环的烯基、非共轭于环丙烷环的烯基、环烷基、环烯基和杂环；R选自OH和OR'，其中R'选自可能被取代的低级烷基、可能被取代在苯基或亚甲基部分的苄基、N-亚甲基二羧亚胺、(5-苄基-呋喃-3)甲基，以及通式为##STR2##的环戊烯，其中R"选自烷基、炔基、烯基、芳基、芳烷基、环烷基、环烯基和杂环；A为选自以下结构的二价烷基基团：##STR3##其中R1选自氢和低级烷基，R2和R3选自烷基、炔基、烯基、芳基、芳烷基、环烷基、环烯基和杂环，并与它们所连接的碳原子一起形成选自3至7个碳原子的碳同环和非饱和碳同环以及可能被低级烷基或低级烷氧基取代的杂环环，R2和R3可以一起形成多环芳香族基团，R4为低级烷基，R5选自氢和低级烷基，且R4和R5与它们所连接的碳原子一起可以形成饱和或非饱和碳同环或杂环环，Y选自亚甲基和饱和或非饱和碳链，Y'选自甲川基和饱和或非饱和碳链，但当Z1和Z2为甲基且R1为氢时，R2不得为甲基，以及它们的制备方法。
• Condensation Reactions of Sulfonylcarbanion
  作者：Yasusi Yamamoto、Tetuya Nisimura、Hitosi Nozaki

  DOI：10.1246/bcsj.44.541

  日期：1971.2

  following the change in the D-content during the reaction of 9-deuterioanthracene. The transformation of the negatively-charged σ-complex into the methylated product involves the concerted occurrence of a hydride shift and the elimination of the sulfinate anion. Meanwhile, the reaction of this carbanion with anthracene at a higher temperature yields the ethylated products of 9-ethyl-10-methyl- and 9,10-diethylanthracene

  苯磺酰基碳负离子 PhSO2CH2− 与 HMPA 中的蒽和吖啶反应得到甲基化产物，就像 DMSO 中的甲基亚磺酰基碳负离子 MeSOCH2− 一样。通过跟踪9-氘代蒽反应过程中D-含量的变化来研究反应机理。带负电荷的 σ 复合物向甲基化产物的转化涉及氢化物转移的协同发生和亚磺酸根阴离子的消除。同时，该碳负离子与蒽在较高温度下反应，除生成 9,10-二甲基蒽外，还生成 9-乙基-10-甲基-和 9,10-二乙基蒽的乙基化产物。碳负离子的其他缩合反应包括 (a) Ph2C=CH2, (b) PhC≡Cph, (c) Ph2CO, (d) PhCOCOPh, 和 (e) 2-氨基二苯甲酮，主要产物是 (a) (评论：
• A base-controlled regioselective synthesis of allyl and vinyl phenyl sulfones
  作者：Dibyendu Dana、Anibal R. Davalos、Gopal Subramaniam、Nisar Afzal、William H. Hersh、Sanjai Kumar

  DOI：10.1016/j.tetlet.2013.03.056

  日期：2013.5

  2-arylacetaldehydes in the presence of a catalytic excess of sodium hydride (1.1 equiv) yields allyl phenyl sulfones in excellent yield under mild reaction conditions. In contrast, when less than 1 equiv of sodium hydride (0.90 equiv) is used, the corresponding vinyl phenyl sulfones are obtained exclusively. The vinyl phenyl sulfones can be completely converted to allyl phenyl sulfones with only 0.2 equiv

  在催化过量的氢化钠（1.1当量）存在下，苯磺酰基甲基膦酸二乙酯与2-芳基乙醛的反应在温和的反应条件下以优异的收率得到烯丙基苯砜。相反，当使用少于1当量的氢化钠（0.90当量）时，仅获得相应的乙烯基苯基砜。仅用0.2当量的NaH就可以将乙烯基苯基砜完全转化为烯丙基苯基砜，这表明参与上述转化的第二种氢化物是催化性的。在这些反应中观察到的区域选择性控制提供了一种从相同的原料一步合成新型乙烯基和烯丙基苯基砜的通用方法。但是，该反应的区域选择性和立体选择性 当2-烷基乙醛与苯基磺酰基甲基膦酸二乙酯在相同的反应条件下反应时，它们的官能度不能保持。我们的结果表明，对于观察到的区域和立体选择性，需要由2-芳基乙醛反应形成的烯丙基砜中双键的扩展共轭。
• One‐Pot Synthesis of Allylic Sulfones, Ketosulfones, and Triflyl Allylic Alcohols from Domino Reactions of Allylic Alcohols with Sulfinic Acid under Metal‐Free Conditions
  作者：Xue‐Qiang Chu、Hua Meng、Xiao‐Ping Xu、Shun‐Jun Ji

  DOI：10.1002/chem.201500469

  日期：2015.8.3

  A metal‐free tandem procedure by using a sulfonylation reaction of aryl allylic alcohols followed by an iodobenzenediacetate (PIDA)‐promoted oxidative functionalization has been established. Allylic sulfones, γ‐ketosulfones, and triflyl allylic alcohols have been constructed in a single operation. The methodology incorporates the sulfonyl (both aryl and triflyl) functionality with a simple work‐up

  通过建立芳基烯丙醇的磺酰化反应，然后由碘代苯二乙酸酯（PIDA）促进氧化功能化，建立了无金属串联程序。烯丙基砜，γ-酮砜和三氟烯丙基烯丙醇可通过一次操作构建。该方法结合了磺酰基（芳基和triflyl）功能，并具有简单的后处理步骤。
• Novel cyclopropanecarboxylic acids and esters
  申请人：Roussel Uclaf

  公开号：US04206140A1

  公开（公告）日：1980-06-03

  Novel cyclopropanecarboxylic acids and esters of the formula ##STR1## wherein Z.sub.1 and Z.sub.2 are selected from the group consisting of hydrogen, alkyl, aralkyl, aryl, alkenyl non-conjugated with the cyclopropane ring, alkynyl non-conjugated with the cyclopropane ring, cycloalkyl, cycloalkenyl and heterocyclic; R is selected from the group consisting of OH and OR' in which R' is selected from the group consisting of lower alkyl which may be substituted, benzyl which may be substituted on the phenyl or methylene portion, N-methylene-dicarboximide, (5-benzyl-furyl-3) methyl, and a cyclopentene of the formula ##STR2## wherein R" is selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic; A is a bivalent alkyl radical selected from the group consisting of ##STR3## wherein R.sub.1 is selected from the group consisting of hydrogen and lower alkyl, R.sub.2 and R.sub.3 are selected from the group consisting of alkyl, alkynyl, alkenyl, aryl, aralkyl, cycloalkyl, cycloalkenyl and heterocyclic and taken together with the carbon atom to which they are attached form a ring selected from the group consisting of carbon homo rings and unsaturated carbon homo rings of 3 to 7 carbon atoms and heterocyclic rings which may be substitued with lower alkyl or lower alkoxy and R.sub.2 and R.sub.3 may together form a polycyclic aromatic radical, R.sub.4 is lower alkyl, R.sub.5 is selected from the group consisting of hydrogen and lower alkyl and R.sub.4 and R.sub.5 together with the carbon atoms to which they are attached may form a saturated or unsaturated carbon homo ring or a heterocyclic ring, Y is selected from the group consisting of methylene and a saturated or unsaturated carbon chain and Y' is selected from the group consisting of methine and a saturated or unsaturated carbon chain with the proviso that when Z.sub.1 and Z.sub.2 are methyl and R.sub.1 is hydrogen, R.sub.2 is other than methyl and their preparation.

  化合物的名称为新型环丙烷羧酸和酯，其化学式为##STR1##其中Z.sub.1和Z.sub.2选择自氢、烷基、芳基烷基、芳基、不与环丙烷环共轭的烯基、不与环丙烷环共轭的炔基、环烷基、环烯基和杂环；R选择自OH和OR'，其中R'选择自可以被取代的低烷基、可以在苯环或亚甲基部分上被取代的苄基、N-亚甲基-二酰亚胺、(5-苄基呋喃-3)甲基和化学式为##STR2##其中R"选择自烷基、炔基、烯基、芳基、芳基烷基、环烷基、环烯基和杂环；A是一个双价烷基基团，选择自##STR3##其中R.sub.1选择自氢和低烷基，R.sub.2和R.sub.3选择自烷基、炔基、烯基、芳基、芳基烷基、环烷基、环烯基和杂环，并与它们附着的碳原子一起形成选择自碳同系环和不饱和碳同系环的3至7个碳原子和杂环环，该杂环环可以用低烷基或低烷氧基取代，R.sub.2和R.sub.3可以共同形成多环芳香基团，R.sub.4是低烷基，R.sub.5选择自氢和低烷基，R.sub.4和R.sub.5与它们附着的碳原子一起可以形成饱和或不饱和的碳同系环或杂环，Y选择自亚甲基和饱和或不饱和的碳链，Y'选择自亚甲基和饱和或不饱和的碳链，但是当Z.sub.1和Z.sub.2为甲基且R.sub.1为氢时，R.sub.2除了甲基外，还有其他基团。这些化合物的制备方法也在描述中提及。