(9CI)-3-乙炔-2,5-二甲基噻吩 | 127798-29-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 中文名称: (9CI)-3-乙炔-2,5-二甲基噻吩
• 英文名称: 3-ethynyl-2,5-dimethylthiophene
• CAS: 127798-29-2
• 化学式: C₈H₈S
• 分子量: 136.218
• InChiKey: ZKVKXKISMSFNNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

反应信息

• 作为反应物：
  描述：

  (9CI)-3-乙炔-2,5-二甲基噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三氯硅烷 、 二异丙胺 、 三苯基膦 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 3-[2-(2,5-Dimethylthiophen-3-yl)-1-phenylphosphindol-3-yl]-2,5-dimethylthiophene
  参考文献：
  名称：

  [EN] ROBUST PHOTOCHROMIC COMPOUNDS WITH SILICON- OR PHOSPHORUS-CONTAINING HETEROCYCLIC RING AND PRODUCTION THEREOF
  [FR] COMPOSÉS PHOTOCHROMIQUES ROBUSTES COMPORTANT UN CYCLE HÉTÉROCYCLIQUE CONTENANT DU PHOSPHORE OU DU SILICIUM ET LEURS PROCÉDÉS DE PRODUCTION

  摘要：

  在一个实施方案中，提供了一种新型的含有二芳基乙烯的光致变色化合物，该化合物将含有硅或磷的杂环引入到二芳基乙烯主链的“乙烯”部分，已经显示出能够展现出可调节、稳健且热稳定的光致变色性能。同时，还提供了合成这些化合物的方法，以及这些化合物的用途，因为它们可以用作光记录材料和其他光功能设备中的光致变色层。

  公开号：

  WO2015188790A1
• 作为产物：
  描述：

  3-碘-2,5-二甲基噻吩 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 生成 (9CI)-3-乙炔-2,5-二甲基噻吩
  参考文献：
  名称：

  二芳基环丁烯的合成和光异构化

  摘要：

  通过钴催化的[2 + 2]环加成反应，由炔烃前体以20-70％的产率合成对称和不对称取代的二芳基环丁烯。反应在温和的条件下进行，并提供了获得不同取代的二芳基乙烯衍生物的途径。在紫外线/可见光照射下，所有二芳基环丁烯产物均经历可逆的光异构化。闭环异构体对再异构化表现出不同的热稳定性，半衰期为9至300小时。 二芳基乙烯-光开关-环丁烯-光致变色反应-[2 + 2]环加成

  DOI：

  10.1055/s-0030-1258435

文献信息

• Synthesis and polymerization of ethynylthiophenes and ethynylfurans containing trifluoromethyl groups
  作者：Masakazu Nishida、Shozo Fujii、Toshiki Aoki、Yoshio Hayakawa、Hiroshige Muramatsu、Tomohiko Morita

  DOI：10.1016/s0022-1139(00)82929-2

  日期：1990.3

  Fluorination of thiophenedicarboxylic acid with sulfur tetrafluoride in the presence of anhydrous hydrogen fluoride provided mono and bis(trifluoromethyl)thiophenes in moderate yields. Ethynylthiophenes and ethynylfurans containing trifluoromethyl groups were prepared via 2,2-dichloro-1-fluorovinyl compounds. In polymerizations using transition metal catalysts, 3-ethynylthiophenes gave polymers in

  在无水氟化氢存在下用四氟化硫氟化噻吩二甲酸可得到中等产率的单和双（三氟甲基）噻吩。通过2，2-二氯-1-氟乙烯基化合物制备含有三氟甲基的乙炔基噻吩和乙炔基呋喃。在使用过渡金属催化剂的聚合中，3-乙炔基噻吩以高收率得到聚合物，其可溶于THF和/或氟化合物，而2-乙炔基噻吩以低收率进行聚合。在γ射线诱导的聚合中，仅2，5-双（三氟甲基）-3-乙炔基噻吩提供了相应的聚合物。通过引入三氟甲基和甲基，提高了获得的聚合物的热分解温度。
• A Highly Efficient Silole-Containing Dithienylethene with Excellent Thermal Stability and Fatigue Resistance: A Promising Candidate for Optical Memory Storage Materials
  作者：Jacky Chi-Hung Chan、Wai Han Lam、Vivian Wing-Wah Yam

  DOI：10.1021/ja5101855

  日期：2014.12.10

  Diarylethene compounds are potential candidates for applications in optical memory storage systems and photoswitchable molecular devices; however, they usually show low photocycloreversion quantum yields, which result in ineffective erasure processes. Here, we present the first highly efficient photochromic silole-containing dithienylethene with excellent thermal stability and fatigue resistance. The photochemical quantum yields for photocyclization and photocycloreversion of the compound are found to be high and comparable to each other; the latter of which is rarely found in diarylethene compounds. These would give rise to highly efficient photoswitchable material with effective writing and erasure processes. Incorporation of the silole moiety as a photochromic dithienylethene backbone also was demonstrated to enhance the thermal stability of the closed form, in which the thermal backward reaction to the open form was found to be negligible even at 100 °C, which leads to a promising candidate for use as photoswitchable materials and optical memory storage.
• Palladium-Catalyzed Aminocarbonylation of Alkynes to Succinimides
  作者：Huizhen Liu、Genevieve P. S. Lau、Paul J. Dyson

  DOI：10.1021/jo502412v

  日期：2015.1.2

  Succinimide derivatives are useful building blocks for the synthesis of natural products and drugs. We describe an efficient route to succinimide derivatives comprising Pd(xantphos)Cl2-catalyzed aminocarbonylation of alkynes with aromatic or aliphatic amines in the presence of p-TsOH. The utility of this route is demonstrated with the synthesis of a large number of succinimide compounds including an important photochromic molecule.
• ROBUST PHOTOCHROMIC COMPOUNDS WITH SILICON- OR PHOSPHORUS-CONTAINING HETEROCYCLIC RING AND THE PRODUCTION THEREOF
  申请人：THE UNIVERSITY OF HONG KONG

  公开号：US20150361332A1

  公开（公告）日：2015-12-17

  In one embodiment, provided are a new class of diarylethene-containing photochromic compounds with the incorporation of silicon- or phosphorus-containing heterocycles into the “ethene” part of the diarylethene backbone that has been shown to be capable of displaying tunable, robust and thermally stable photochromic properties. Also provided are methods for synthesizing these compounds, as well as uses of these compounds as these compounds may be used as the photochromic layer in an optical recording material and other optical functioning devices.
• SILICON-BASED ENERGY STORAGE DEVICES WITH FUNCTIONAL THIOPHENE COMPOUNDS OR DERIVATIVES OF THIOPHENE CONTAINING ELECTROLYTE ADDITIVES
  申请人：Enevate Corporation

  公开号：US20200388881A1

  公开（公告）日：2020-12-10

  Electrolytes and electrolyte additives for energy storage devices comprising functional thiophene compounds are disclosed. The energy storage device comprises a first electrode and a second electrode, wherein at least one of the first electrode and the second electrode is a Si-based electrode, a separator between the first electrode and the second electrode, an electrolyte, and at least one electrolyte additive selected from a thiophene compound.