cis-1-methyl-4-(2-methylsulfanylvinyl)benzene | 55059-14-8

• 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: cis-1-methyl-4-(2-methylsulfanylvinyl)benzene
• 英文别名: cis-2-(4-methylphenyl)-1-methylthioethylene；methyl(4-methylstyryl)sulfane；(Z)-1-Methylthio-2-(4-methylphenyl)ethylen；1-methyl-4-[(Z)-2-methylsulfanylethenyl]benzene
• CAS: 55059-14-8
• 化学式: C₁₀H₁₂S
• 分子量: 164.271
• InChiKey: UUOBEZAFKAWOIC-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-1-methyl-4-(2-methylsulfanylvinyl)benzene 在 甲烷磺酸 作用下， 生成 cis-β-(4-Methyl-styryl)-methyl-sulfon
  参考文献：
  名称：

  Wegener, Wolfgang; Palm, Dietrich; Schleinitz, Klaus-Dieter, Zeitschrift fur Chemie, 1982, vol. 22, # 6, p. 218 - 219

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲苯基乙炔 在 acetylacetonatodicarbonylrhodium(l) 、 正丁基锂 、 氢气 、 6,6′-[(3,3′-二叔丁基-5,5′-二甲氧基-1,1′-二苯基-2,2′-二基)双(氧)]双(二苯并[d,f][1,3,2]二噁磷杂庚英) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， -78.0~40.0 ℃ 、500.01 kPa 条件下， 反应 18.5h， 生成 cis-1-methyl-4-(2-methylsulfanylvinyl)benzene
  参考文献：
  名称：

  炔基硫醚的加氢甲酰化：生成 α-磺基丙烯醛的立体和区域选择性途径

  摘要：

  描述了在温和条件下铑催化的炔基硫醚的加氢甲酰化反应。该方法可以获得具有良好区域选择性（α/β 比例高达 89/11）的 α-硫基丙烯醛，并且适用于各种取代的底物。它甚至对更复杂的底物（例如半胱氨酸和胆固醇衍生物）也有效。为了证明所得产物的合成潜力，选择(Z)-3-环己基-2-甲基硫基丙烯醛为例，将其硫原子选择性氧化成相应的亚砜或砜。在氧化过程中，酸促进双键从 (Z) 异构化为 (E)。然后将获得的三种硫基、亚磺酰基和磺酰基官能化丙烯醛用作亲二烯体以制备环己烯甲醛。

  DOI：

  10.1002/adsc.202301349

文献信息

• Selective Synthesis of cis-α,β-Unsaturated Sulfoxides and Sulfides by the Horner-Wittig Reaction with Bis(2,2,2-trifluoroethyl)phosphono Sulfoxides and Aromatic Aldehydes
  作者：Keisuki Kokin、Shuji Tsuboi、Jiro Motoyoshiya、Sadao Hayashi

  DOI：10.1055/s-1996-4268

  日期：1996.5

  cis-α,β-Unsaturated sulfoxides were predominantly formed in the Horner-Wittig reaction with bis(2,2,2-trifluoroethyl)phosphono sulfoxides and aromatic aldehydes, while the reaction of the corresponding sulfides showed trans- or lower cis-selectivity. The reduction of cis-α,β-unsaturated sulfoxides with tributylphosphine in carbon tetrachloride gave cis-vinyl sulfides with retention of stereochemistry.

  在与双(2,2,2-三氟乙基)磷酸亚磺酰和芳香醛的霍纳-维蒂格反应中，主要形成了顺-α,β-不饱和亚磺酰，而相应硫化物的反应则表现出反式或较低的顺选择性。用三丁基磷在四氯化碳中还原顺-α,β-不饱和亚磺酰产生了保持立体化学的顺-乙烯基硫化物。
• Cobalt modified N-doped carbon nanotubes for catalytic CC bond formation <i>via</i> dehydrogenative coupling of benzyl alcohols and DMSO
  作者：Jinlei Li、Guoliang Liu、Lijun Shi、Qi Xing、Fuwei Li

  DOI：10.1039/c7gc02335a

  日期：——

  The development of heterogeneous, cost-effective and environmentally benign catalysts to construct CC bonds is highly desirable.

  开发多元化、具有成本效益且环境友好的催化剂来构建C-C键是非常可取的。
• Aldehyde to Ketone Homologation Enabled by Improved Access to Thioalkyl Phosphonium Salts
  作者：Meghan Fragis、Jackson L. Deobald、Srinivas Dharavath、Jeffrey Scott、Jakob Magolan

  DOI：10.1021/acs.orglett.1c01189

  日期：2021.6.18

  to competing redox chemistry with sulfoxides. Here we circumvent this problem to achieve a formal phosphine Pummerer reaction that offers thioalkyl phosphonium salts that, in turn, give rise to diverse vinyl sulfides via Wittig olefinations. Thirty vinyl sulfides are thus prepared from (alkylthioalkyl)triphenyl phosphonium salts and aldehydes. The hydrolysis of these vinyl sulfides offers an efficient

  由于与亚砜的氧化还原化学竞争，膦以前不能用作 Pummerer 型亲核试剂。在这里，我们绕过这个问题以实现正式的膦普默勒反应，该反应提供硫代烷基鏻盐，进而通过 Wittig 烯化产生多种乙烯基硫化物。因此由(烷硫基烷基)三苯基鏻盐和醛制备三十种乙烯基硫化物。这些乙烯基硫化物的水解提供了醛到酮的高效且多功能的两步单碳同系化。
• Desulfonylation of α-Methylthio-α,β-unsaturated Sulfones. A New Route to One Carbon Homologation of Aromatic Aldehydes
  作者：Xian Huang、Han-Zhong Zhang

  DOI：10.1055/s-1989-27143

  日期：——

  α-Methylthio-α,β-unsaturated sulfones 3 prepared from aromatic aldehydes 1 and sulfone 2 react with sodium hydrogen telluride in ethanol to undergo reductive desulfonylation to give vinyl sulfides 4 with certain extent of stereospecificity. A new route to one carbon homologation of aromatic aldehydes 1 to 5 is achieved by hydrolysis of 4 with titanium tetrachloride.

  由芳香醛 1 和砜 2 制备的δ-甲硫基-δ,δ-不饱和砜 3 与碲化氢钠在乙醇中发生还原性脱磺反应，生成具有一定立体特异性的乙烯基砜 4。芳香醛 1 至 5 的单碳同源化新途径是通过 4 与四氯化钛的水解来实现的。
• ORGANIC TRANSISTOR, COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL FOR NON-LIGHT-EMITTING ORGANIC SEMICONDUCTOR DEVICE, MATERIAL FOR ORGANIC TRANSISTOR, COATING LIQUID FOR NON-LIGHT-EMITTING ORGANIC SEMICONDUCTOR DEVICE, METHOD FOR MANUFACTURING ORGANIC TRANSISTOR, METHOD FOR MANUFACTURING ORGANIC SEMICONDUCTOR FILM, ORGANIC SEMICONDUCTOR FILM FOR NON-LIGHT-EMITTING ORGANIC SEMICONDUCTOR DEVICE, AND METHOD FOR SYNTHESIZING ORGANIC SEMICONDUCTOR MATERIAL
  申请人：Fujifilm Corporation

  公开号：EP3125322A1

  公开（公告）日：2017-02-01

  Provided are an organic transistor with high carrier mobility having a semiconductor active layer containing a compound which is represented by the following formula and has a molecular weight of equal to or less than 3,000, a compound, an organic semiconductor material for a non-light-emitting organic semiconductor device, a material for an organic transistor, a coating solution for a non-light-emitting organic semiconductor device, a method for manufacturing an organic transistor, a method for manufacturing an organic semiconductor film, an organic semiconductor film for a non-light-emitting organic semiconductor device, and a method for manufacturing an organic semiconductor material. (X represents an oxygen, sulfur, selenium, or tellurium atom or NR5; Y and Z each represents CR6, an oxygen, sulfur, selenium, or nitrogen atom, or NR7; a ring containing Y and Z is an aromatic heterocycle; any one of R1 and R2 and the aromatic heterocycle containing Y and Z or any one of R3 and R4 and a benzene ring may be bonded to each other through a specific divalent linking group; R1, R2, and R5 to R8 each represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heteroaryl group; R3 and R4 each represent an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or heteroaryl group; and each of m and n is an integer of 0 to 2.)

  本发明提供了一种具有高载流子迁移率的有机晶体管，该晶体管的半导体有源层含有分子量等于或小于3000的下式表示的化合物、化合物、用于非发光有机半导体器件的有机半导体材料、用于有机晶体管的材料、用于非发光有机半导体器件的涂层溶液、制造有机晶体管的方法、制造有机半导体薄膜的方法、用于非发光有机半导体器件的有机半导体薄膜以及制造有机半导体材料的方法。 (X代表氧原子、硫原子、硒原子或碲原子或NR5；Y和Z各自代表CR6、氧原子、硫原子、硒原子或氮原子或NR7；含有Y和Z的环是芳香杂环；R1和R2中的任一个与含有Y和Z的芳香杂环或R3和R4中的任一个与苯环可通过特定的二价连接基团相互键合；R1、R2 和 R5 至 R8 分别代表氢原子、烷基、烯基、炔基、芳基或杂芳基；R3 和 R4 分别代表烷基、烯基、炔基、芳基或杂芳基；以及 m 和 n 分别为 0 至 2 的整数。)