苯,1-溴-3-[(苯磺酰)甲基]- | 130891-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯,1-溴-3-[(苯磺酰)甲基]-
• 英文名称: 3-bromobenzyl phenyl sulfone
• 英文别名: 1-Bromo-3-[(phenylsulfonyl)methyl]benzene；1-(benzenesulfonylmethyl)-3-bromobenzene
• CAS: 130891-01-9
• 化学式: C₁₃H₁₁BrO₂S
• 分子量: 311.199
• InChiKey: UYMGKBXLDYZFOF-UHFFFAOYSA-N

物化性质

• 沸点：
  474.0±37.0 °C(Predicted)
• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  苯,1-溴-3-[(苯磺酰)甲基]- 在 [Pd(PPh₃)4)] copper(l) iodide 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 Pentadecacyclo[81.3.1.126,30.133,37.140,44.169,73.176,80.04,13.07,12.014,23.015,20.047,56.050,55.057,66.058,63]dononaconta-1(86),4(13),5,7,9,11,14(23),15,17,19,21,26,28,30(92),33(91),34,36,40(90),41,43,47(56),48,50,52,54,57(66),58,60,62,64,69,71,73(89),76,78,80(88),83(87),84-octatriacontaen-2,24,31,38,45,67,74,81-octayne
  参考文献：
  名称：

  Sulfoximine Version of Double Elimination Protocol for Synthesis of Chiral Acetylenic Cyclophanes

  摘要：

  A new strategy for constructing enantiopure acetylenic cyclophanes is described on the basis of one-pot double elimination reaction starting from dialdehydes and bis(sulfoximine)s. In this case, the conventional sulfone protocol affords poorer yields of the desired cyclophanes. Thus, arylene-ethynylene moieties with terminal sulfoximine or formyl functions are linked to binaphthyl cores and these building blocks are then subjected to double elimination reaction. The desired macrocycles are obtained in up to 35% yield. The corresponding Sonogashira coupling fails to afford cyclophanes indicative of effectiveness of the double elimination methodology.

  DOI：

  10.1002/1521-3765(20020503)8:9<2005::aid-chem2005>3.0.co;2-i
• 作为产物：
  描述：

  3-溴苄溴 、 sodium benzenesulfonate 以 N,N-二甲基甲酰胺 为溶剂， 生成 苯,1-溴-3-[(苯磺酰)甲基]-
  参考文献：
  名称：

  抗酸的不对称全合成。

  摘要：

  描述了使用生物启发的多烯环化策略进行的对乙酸的首次不对称全合成。获得了良好的收率和良好的不对称诱导。

  DOI：

  10.1021/ol800499p

文献信息

• Custom-Made Pyrene Photocatalyst-Promoted Desulfonylation of Arylethenyl Sulfones Using Green-Light-Emitting Diodes
  作者：Akihiro Orita、Hikaru Watanabe、Kazuki Nakajima、Kento Ekuni、Ryota Edagawa、Yuta Akagi、Yasuhiro Okuda、Kan Wakamatsu

  DOI：10.1055/s-0040-1706025

  日期：2021.9

  3,6,8-tetrabromopyrene with 4-[(–)-β-citronellyloxy]phenylethyne was employed to synthesize 1,3,6,8-tetra[4-(citronellyloxy)phenylethynyl]pyrene. The pyrene derivative catalyzed the reductive desulfonylation of ethenyl sulfones via visible-light irradiation (514 nm green light-emitting diodes) in the presence of i-Pr2NEt. The β-citronellyloxy groups provided the sufficient solubility to the highly

  1,3,6,8-四溴py与4-[（-）-β-香茅基氧基]苯基乙炔的Sonogashira偶联用于合成1,3,6,8-四[4-（香茅基氧基）苯基乙炔基]]。i衍生物在i -Pr 2 NEt存在下，通过可见光照射（514 nm绿色发光二极管）催化乙烯基砜的还原性脱磺酰化反应。β-香柠檬烯氧基为高度π-膨胀的pyr催化剂提供了足够的溶解度，并且它们的极性氧官能团使得可以通过柱色谱法容易地从产物中分离出催化剂。
• Syntheses of Diarylethenes by Perylene-catalyzed Photodesulfonylation from Ethenyl Sulfones
  作者：Hikaru Watanabe、Mai Takemoto、Kazumasa Adachi、Yasuhiro Okuda、Aki Dakegata、Takahide Fukuyama、Ilhyong Ryu、Kan Wakamatsu、Akihiro Orita

  DOI：10.1246/cl.200046

  日期：2020.4.5

  Diarylethenes were obtained from the corresponding ethenyl sulfones by photocatalyzed desulfonylation using UV or blue LEDs. When perylene and i-Pr2NEt were used as a photocatalyst and a sacrificing reagent, respectively, this desulfonylation proceeded smoothly to afford the desired ethenes with the functional groups such as chloro, alkoxy and heteroaromatic rings remaining untouched. The use of a flow photoreactor enabled this desulfonylation to proceed more rapidly to finish in an hour of residence time.

  通过使用UV或蓝光LED进行光催化脱磺反应，从相应的乙烯基砜中获得了二芳基乙烯。当使用苝和i-Pr2NEt分别作为光催化剂和牺牲剂时，这种脱磺反应顺利进行，得到的目标乙烯化合物中的功能团（如氯、烷氧基和杂芳环）保持不变。使用流动型光反应器使这种脱磺反应能够更快地完成，在停留时间为一小时内即可完成。
• Double Elimination Protocol for Convenient Synthesis of Dihalodiphenylacetylenes: Versatile Building Blocks for Tailor-Made Phenylene-Ethynylenes
  作者：Akihiro Orita、Kazuhiko Miyamoto、Mikio Nakashima、Fangguo Ye、Junzo Otera

  DOI：10.1002/adsc.200404014

  日期：2004.6

  Dihalodiphenylacetylenes are conveniently synthesized by a double elimination reaction of β-substituted sulfones which are readily obtained from halogen-substituted benzyl sulfone and benzaldehyde derivatives. Halogens can be incorporated at any desired positions in the diphenylacetylene skeleton simply by choosing the substitution position of the halogen on the aromatic rings of the starting compounds

  二卤代二苯基乙炔可通过β-取代的砜的双消除反应方便地合成，所述β-取代的砜容易从卤素取代的苄基砜和苯甲醛衍生物获得。仅通过选择起始化合物的芳环上卤素的取代位置，就可以在二苯乙炔骨架中的任何所需位置掺入卤素。由此获得的具有不同卤素取代基的二苯基乙炔由于卤素的不同反应性而经历了顺序的碳-碳键形成。因此，可以在任何位置的二苯基乙炔骨架上结合各种部分，从而可以设计各种具有调节的结构和组成的量身定制的亚苯基-亚乙炔基。
• 1,2-Diarylethenyl Sulfones: Readily-Prepared Masked Diarylethynes for Access to Aryleneethynylenes
  作者：Akihiro Orita、Junzo Otera、Takashi Doi、Daisuke Matsuo、Ryosuke Saijo

  DOI：10.1055/s-2007-990924

  日期：2008.1

  1,2-Di(halophenyl)ethenyl phenyl sulfones were prepared readily by successive treatment of halophenylmethyl sulfones with LiHMDS (lithium hexamethyldisilazide), halobenzaldehydes, diethyl chlorophosphate and LiHMDS. The di(halophenyl)ethenyl sulfones thus obtained were transformed successfully to aryleneethynylenes by Sonogashira coupling with arylethyne followed by LiHMDS-promoted elimination of phenylsulfinic acid.

  通过用六甲基二硅氮化锂（LiHMDS）、卤代苯甲醛、氯磷酸二乙酯和六甲基二硅氮化锂连续处理卤代苯甲基砜，可以很容易地制备出 1,2-二（卤苯基）乙烯基苯砜。这样得到的二（卤苯基）乙烯基砜通过与芳基乙炔的 Sonogashira 偶联，然后在 LiHMDS 的促进下消除苯亚磺酸，成功地转化为芳基乙炔。
• Templated Synthesis of End-Functionalized Graphene Nanoribbons through Living Ring-Opening Alkyne Metathesis Polymerization
  作者：Stephen von Kugelgen、Ilya Piskun、James H. Griffin、Christopher T. Eckdahl、Nanette N. Jarenwattananon、Felix R. Fischer

  DOI：10.1021/jacs.9b01805

  日期：2019.7.17

  the sequence, and the end groups of GNRs. Here, we report the living chain-growth synthesis of chevron-type GNRs (cGNRs) templated by a poly-(arylene ethynylene) precursor prepared through ring-opening alkyne metathesis polymerization (ROAMP). The strained triple bonds of a macrocyclic monomer serve both as the site of polymerization and the reaction center for an annulation reaction that laterally

  原子精确自下而上合成的石墨烯纳米带（GNR）是下一代电子材料的有希望的候选者。将这些高度可调的半导体结合到复杂的器件架构中，需要开发合成工具来控制 GNR 的绝对长度、序列和端基。在这里，我们报告了通过开环炔复分解聚合 (ROAMP) 制备的聚（亚芳基乙炔）前体模板化的 V 型 GNR（cGNR）的活性链生长合成。大环单体的应变三键既是聚合位点，也是环化反应的反应中心，环化反应横向延伸共轭主链，得到具有预定长度和端基的 cGNR。