(E)-2-[2-(1-naphthyl)vinyl]benzothiazole | 30216-41-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-[2-(1-naphthyl)vinyl]benzothiazole
• 英文别名: 2-(2-naphthalen-1-yl-vinyl)-benzothiazole；2-[(E)-2-naphthalen-1-ylethenyl]-1,3-benzothiazole
• CAS: 30216-41-2
• 化学式: C₁₉H₁₃NS
• 分子量: 287.385
• InChiKey: GHHRACMERDGPLU-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-[2-(1-naphthyl)vinyl]benzothiazole 以1%的产率得到2-[(Z)-2-naphthalen-1-ylethenyl]-1,3-benzothiazole
  参考文献：
  名称：

  反式-顺式异构化引发的萘基乙烯基苯并恶唑类针状晶体的光诱导弯曲

  摘要：

  合成了含有苯并恶唑（NBO）和苯并噻唑（NBT）的新的二芳基乙烯衍生物。NBO和NBT的光诱导反式-顺式异构化发生在晶体中，并且仅诱导NBO的针状晶体向后弯曲，远离紫外光源。原子的运动被认为是在NBO的异构化过程中发生的; 因此，应变将在暴露于紫外线的晶体表面迅速产生并积累。应变的均匀释放导致针状晶体弯曲。光致反式-顺NBT的异构化效率太低，无法驱动晶体的运动，这可能是由于萘基与苯并噻唑之间的排斥力较大而引起的。这些结果为通过二芳基乙烯衍生物的单分子光化学反应将光能转化为分子晶体中的机械能提供了新的平台。

  DOI：

  10.1002/asia.201800380
• 作为产物：
  描述：

  (E)-2-[2-(1-naphthyl)vinyl]-3-tosyl-2,3-dihydro-1,3-benzothiazole 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到(E)-2-[2-(1-naphthyl)vinyl]benzothiazole
  参考文献：
  名称：

  钯-铜催化具有两个杂原子的苯并稠合杂环的合成：（E）-2-（2-芳基乙烯基）-3-甲苯基-2,3-二氢-1,3-苯并噻唑和（ E）-2-烷基（芳基）亚烷基-3,4-二氢-2H-1,4-苯并噻嗪。

  摘要：

  已开发出一种高度新颖，通用且方便的钯和铜催化方法，用于合成（E）-2-（2-芳基乙烯基）-3-甲苯磺酰基-2,3-二氢-1,3-苯并噻唑28- 40 3-（2-氨基苯硫基）丙-1-炔1在钯-铜催化下与芳基碘化物2-14反应生成双取代炔烃15-27，甲苯磺酸化后，在THF中在三乙胺存在下用CuI进行新型环化反应（E）-2-（2-芳基乙烯基）-3-甲苯基-2,3-二氢-1,3-苯并噻唑28-40，而不是预期的3-亚烷基-4-甲苯基-3,4-二氢-2H -1,4-苯并噻嗪41.反应具有很高的区域选择性和立体选择性。还报道了2-（2-芳基乙基）-3-甲苯基苯并噻唑啉42-47、2-（2-芳基乙烯基）苯并噻唑48-54和具有潜在生物学重要性的新型5-取代尿嘧啶衍生物55的合成。同样，S- [2-（N-prop-2'-炔基）氨基苯基] -N，N-二甲基硫代氨基甲酸酯58与芳基碘化物的钯铜催化的芳基化反

  DOI：

  10.1021/jo001783+

文献信息

• RESIN COMPOSITION FOR OPTICAL MOLDING
  申请人：Kuraray Noritake Dental Inc.

  公开号：EP3900693A1

  公开（公告）日：2021-10-27

  The present invention provides a resin composition for optical shaping that emits a weaker odor, enables easy fabrication of an object by virtue of its low viscosity, and can be made into a fabricated product having desirable toughness and water resistance when used for stereolithographic fabrication (particularly by vat stereolithography) and that is particularly suited for dental occlusal splints, mouth guards, and denture base materials. The present invention relates to a resin composition for optical shaping comprising: an α,β-unsaturated double bond group-containing compound (A) having a ring structure (a) containing a nitrogen atom; a (meth)acrylic acid ester compound (B) having a boiling point of 280°C or more at normal pressure, having a carbocyclic group, and having no nitrogen-containing heterocyclic group; a photopolymerization initiator (C); and optionally, a polyfunctional polymerizable monomer (E) having a molecular weight of 500 or less and not comprised in the α,β-unsaturated double bond group-containing compound (A) and the (meth)acrylic acid ester compound (B), wherein the content of the polyfunctional polymerizable monomer (E) having a molecular weight of 500 or less is 20 mass% or less relative to the total amount of polymerizable compounds comprised in the resin composition for optical shaping.

  本发明提供了一种用于光学整形的树脂组合物，该组合物散发的气味较弱，因其粘度低而易于制造物体，在用于立体光刻制造（特别是大桶立体光刻）时，可制成具有理想韧性和耐水性的制成品，特别适用于牙科咬合夹板、护齿板和义齿基底材料。本发明涉及一种用于光学塑形的树脂组合物，包括具有含氮原子的环结构 (a) 的含 α、β-不饱和双键基团的化合物 (A)；(甲基) 丙烯酸酯化合物 (B)，在常压下的沸点为 280°C 或更高，具有碳环基团，且不含含氮杂环基团；光聚合引发剂 (C)；以及可选的分子量为 500 或以下且不包含在含α，β-不饱和双键基团的化合物（A）和（甲基）丙烯酸酯化合物（B）中的多功能可聚合单体（E），其中分子量为 500 或以下的多功能可聚合单体（E）的含量占光学成型用树脂组合物中可聚合化合物总量的 20% 或以下。
• Photophysics, photochemistry and thermal stability of diarylethene-containing benzothiazolium species
  作者：Morad M. El-Hendawy、Tarek A. Fayed、Mohamed K. Awad、Niall J. English、Safaa Eldin H. Etaiw、Ahmed B. Zaki

  DOI：10.1016/j.jphotochem.2014.12.015

  日期：2015.3

  The photophysics, photochemistry and thermal stability of four 1-atyl-2-(N-methyl-2-benzothiazolium) ethene iodides (aryl: phenyl, 1-naphthyl, 9-phenanthryl and 9-anthryl) were studied. Although the absorption spectra are found to be hypsochromic-shifted, fluorescence spectra are bathochromic-shifted. The dipole moment in the relaxed excited state was found to be larger than that in the ground state. To investigate effects of N-methylation and the aryl-ring size, a detailed comparison was made between those in the present work (of charged compounds) and previous studies of their neutral analogues, with computed electron affinity and ionisation potentials serving to rationalise the experimentally observed bathochromic shifts in absorption and emission spectra. The kinetics of thermal isomerisation depend strongly on the nature of the aryl moiety and solvent; the larger the aryl ring, the slower the rate of isomerisation. The fastest isomerisation process was found to take place in MeOH. The anthryl derivative did not isomerize either by light- or heat-exposure, due to high energy barriers of rotation around the ethenic bond. Based on the significant blue-shift of the Z-isomer absorption maximum relative to that of the E-isomer, and the high percentage of Z-isomers in the photostationary state, these compounds may serve as potential promising candidates for optical data-storage applications. (C) 2015 Elsevier B.V. All rights reserved.
• RESIN COMPOSITION FOR OPTICAL SHAPING
  申请人：KURARAY NORITAKE DENTAL INC.

  公开号：US20220041777A1

  公开（公告）日：2022-02-10

  A resin composition for optical shaping comprising: an α,β-unsaturated double bond group-containing compound (A) having a ring structure (a) containing a nitrogen atom; a (meth)acrylic acid ester compound (B) having a boiling point of 280° C. or more at normal pressure, having a carbocyclic group, and having no nitrogen-containing heterocyclic group; a photopolymerization initiator (C); and optionally, a polyfunctional polymerizable monomer (E) having a molecular weight of 500 or less and not comprised in the α,β-unsaturated double bond group-containing compound (A) and the (meth)acrylic acid ester compound (B), wherein the content of the polyfunctional polymerizable monomer (E) having a molecular weight of 500 or less is 20 mass % or less relative to the total amount of polymerizable compounds comprised in the resin composition for optical shaping.
• [EN] RESIN COMPOSITION FOR OPTICAL MOLDING<br/>[FR] COMPOSITION DE RÉSINE POUR MOULAGE OPTIQUE<br/>[JA] 光造形用樹脂組成物
  申请人：KURARAY NORITAKE DENTAL INC

  公开号：WO2020129736A1

  公开（公告）日：2020-06-25

  本発明は、光造形（特に液槽光造形）によって造形したときに、臭気が少なく、低粘度で造形しやすく、かつ靭性及び耐水性に優れた造形物を得ることができ、特に歯科用咬合スプリント、マウスガード、義歯床材料に好適な光造形用樹脂組成物を提供する。本発明は、窒素原子を含有する環状構造（ａ）を有するα，β－不飽和二重結合基含有化合物（Ａ）、常圧沸点２８０℃以上で、炭素環基を有し、含窒素複素環基を有しない（メタ）アクリル酸エステル化合物（Ｂ）、光重合開始剤（Ｃ）、並びに、必要に応じて、前記α，β－不飽和二重結合基含有化合物（Ａ）及び前記（メタ）アクリル酸エステル化合物（Ｂ）に含まれない、分子量５００以下の多官能性重合性単量体（Ｅ）を含有し、前記分子量５００以下の多官能性重合性単量体（Ｅ）の含有量が、光造形用樹脂組成物に含まれる重合性化合物の総量に対して２０質量％以下である、光造形用樹脂組成物に関する。
• Light‐Induced Bending of Needle‐Like Crystals of Naphthylvinylbenzoxazole Triggered by <i>trans</i> – <i>cis</i> Isomerization
  作者：Jiang Peng、Jinyu Zhao、Kaiqi Ye、Hongqiang Gao、Jingbo Sun、Ran Lu

  DOI：10.1002/asia.201800380

  日期：2018.7.4

  strain led to the bending of needle‐like crystals. The light‐induced trans–cis isomerization efficiency of NBT was too low to drive the motion of crystals, which might have originated from the large repulsion between naphthyl and benzothiazole. These results provide a new platform for the transformation of light energy into mechanical energy in molecular crystals through the unimolecular photochemical

  合成了含有苯并恶唑（NBO）和苯并噻唑（NBT）的新的二芳基乙烯衍生物。NBO和NBT的光诱导反式-顺式异构化发生在晶体中，并且仅诱导NBO的针状晶体向后弯曲，远离紫外光源。原子的运动被认为是在NBO的异构化过程中发生的; 因此，应变将在暴露于紫外线的晶体表面迅速产生并积累。应变的均匀释放导致针状晶体弯曲。光致反式-顺NBT的异构化效率太低，无法驱动晶体的运动，这可能是由于萘基与苯并噻唑之间的排斥力较大而引起的。这些结果为通过二芳基乙烯衍生物的单分子光化学反应将光能转化为分子晶体中的机械能提供了新的平台。