4-(trifluoroacetylamino)benzo<1,2,5>thiadiazole | 149509-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4-(trifluoroacetylamino)benzo<1,2,5>thiadiazole
• 英文别名: 4-(1-pyrrolidinyl)benzo[c][1,2,5]thiadiazole；4-(pyrrolidin-1-yl)benzo[c][1,2,5]thiadiazole；4-pyrrolidin-1-yl-2,1,3-benzothiadiazole
• CAS: 149509-66-0
• 化学式: C₁₀H₁₁N₃S
• 分子量: 205.283
• InChiKey: ZCPUVWHNXODIHX-UHFFFAOYSA-N

物化性质

• 沸点：
  337.2±15.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.02
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(trifluoroacetylamino)benzo<1,2,5>thiadiazole 在 重氮苯磺酸 、 sodium hydroxide 、 sodium dithionite 作用下， 以 盐酸 为溶剂， 以8%的产率得到4-amino-7-(1-pyrrolidinyl)benzo[c][1,2,5]thiadiazole
  参考文献：
  名称：

  Preparation, Structure, and Amphoteric Redox Properties of p-Phenylenediamine-Type Dyes Fused with a Chalcogenadiazole Unit

  摘要：

  4,7-Bis(dialkylamino)benzo[c] [1,2,5]chalcogenadiazoles are a novel class of organic dyes that undergo reversible two-stage one-electron oxidation as well as one-electron reduction. They exhibit absorption maxima in the long-wavelength region, which are assigned as intramolecular charge transfer bands from the phenylenediamine moiety to the electron-accepting heterocycle. Their redox properties as well as molecular and crystal structures are affected by the alkyl substituents on the amino nitrogen and/or by the chalcogen atom (O, S, Se) in the heterocycle.

  DOI：

  10.1021/jo010808h
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride 、 potassium tert-butylate 、 氢溴酸 、 溴 作用下， 以 水 、 甲苯 为溶剂， 反应 12.0h， 生成 4-(trifluoroacetylamino)benzo<1,2,5>thiadiazole
  参考文献：
  名称：

  NEAR-INFRARED-ABSORBING DYE, OPTICAL FILTER, AND IMAGING DEVICE

  摘要：

  提供的是一种近红外吸收染料，可以增加可见光透射率，并具有近红外阻挡特性。该近红外吸收染料具有通过将染料溶解在二氯甲烷中测量的吸收特性，满足以下要求。在波长为400到800纳米的吸收光谱中，存在一个最大吸收波长λmax，位于670纳米或更高的波长区域。在最大吸收常数εA与光波长为430到550纳米的光的最大吸收常数εB之间建立以下关系表达式，其中εB/εA≥65。在光谱透射曲线中，当最大吸收波长λmax的透射率设定为1%时，波长为430到460纳米的光的平均透射率为94.0%或更高。

  公开号：

  US20180346729A1

文献信息

• Photophysical characterization and fluorescence cell imaging applications of 4-<i>N</i>-substituted benzothiadiazoles
  作者：Susanne Doloczki、Karl O. Holmberg、Ignacio Fdez. Galván、Fredrik J. Swartling、Christine Dyrager

  DOI：10.1039/d2ra01404a

  日期：——

  Herein we report the structure–photophysical relationship and cell imaging utility of a series of N-substituted benzothiadiazoles.

  我们在此报告了一系列N-取代苯并噻二唑的结构-光物理关系和细胞成像效用。
• Photocatalyst-free visible-light triggered amination of benzo[<i>c</i>][1,2,5]thiadiazole: direct C–N bond formation from C(sp²)–H bond
  作者：V. Murugesh、Patlolla Ravinder Reddy、Surya Prakash Singh

  DOI：10.1039/d2cc05811a

  日期：——

  The photoredox amination of arene protocols mostly comprises photocatalyst-mediated transformations. Herein, we presented the photocatalyst-free, visible-light promoted, direct conversion of C(sp2)–H to C(sp2)–N method. Multipurpose benzothiadiazoles are used as model synthons and secondary amines as aminating agents. Mechanistic study reveals that the radical reaction mechanism proceeds through nitrogen-centered

  芳烃协议的光氧化还原胺化主要包括光催化剂介导的转化。在此，我们介绍了无光催化剂、可见光促进的 C(sp 2 )–H 直接转化为 C(sp 2 )–N 的方法。多用途苯并噻二唑用作模型合成子，仲胺用作胺化剂。机理研究表明，自由基反应机制是通过以氮为中心的自由基生成，然后添加芳烃进行的，这在本发明的苯并噻二唑与仲胺的胺化方案中以原子经济方式得到证明。
• Suzuki, Takanori; Okubo, Tsuneyuki; Okada, Akihisa, Heterocycles, 1993, vol. 35, # 1, p. 395 - 406
  作者：Suzuki, Takanori、Okubo, Tsuneyuki、Okada, Akihisa、Yamashita, Yoshiro、Miyashi, Tsutomu

  DOI：——

  日期：——
• NEAR-INFRARED-ABSORBING DYE, OPTICAL FILTER, AND IMAGING DEVICE
  申请人：AGC Inc.

  公开号：US20180346729A1

  公开（公告）日：2018-12-06

  Provided is a near-infrared-absorbing dye increasing a visible light transmittance and having a near-infrared blocking characteristic. The near-infrared-absorbing dye has an absorption characteristic measured by dissolving the dye in dichloromethane satisfying the following requirements. ⋅In an absorption spectrum at a wavelength of 400 to 800 nm, there is a maximum absorption wavelength λ max in a wavelength region of 670 nm or more. ⋅The following relational expression is established between a maximum absorption constant ε A with respect to light with a wavelength of 430 to 550 nm and a maximum absorption constant ε B with respect to light with a wavelength of 670 nm or more, where ε B /ε A ≥65. ⋅In a spectral transmittance curve, an average transmittance of light with a wavelength of 430 to 460 nm is 94.0% or more when a transmittance at the maximum absorption wavelength λ max is set to 1%.

  提供的是一种近红外吸收染料，可以增加可见光透射率，并具有近红外阻挡特性。该近红外吸收染料具有通过将染料溶解在二氯甲烷中测量的吸收特性，满足以下要求。在波长为400到800纳米的吸收光谱中，存在一个最大吸收波长λmax，位于670纳米或更高的波长区域。在最大吸收常数εA与光波长为430到550纳米的光的最大吸收常数εB之间建立以下关系表达式，其中εB/εA≥65。在光谱透射曲线中，当最大吸收波长λmax的透射率设定为1%时，波长为430到460纳米的光的平均透射率为94.0%或更高。
• Preparation, Structure, and Amphoteric Redox Properties of <i>p</i>-Phenylenediamine-Type Dyes Fused with a Chalcogenadiazole Unit
  作者：Takanori Suzuki、Takashi Tsuji、Tsuneyuki Okubo、Akihisa Okada、Yoshiaki Obana、Takanori Fukushima、Tsutomu Miyashi、Yoshiro Yamashita

  DOI：10.1021/jo010808h

  日期：2001.12.1

  4,7-Bis(dialkylamino)benzo[c] [1,2,5]chalcogenadiazoles are a novel class of organic dyes that undergo reversible two-stage one-electron oxidation as well as one-electron reduction. They exhibit absorption maxima in the long-wavelength region, which are assigned as intramolecular charge transfer bands from the phenylenediamine moiety to the electron-accepting heterocycle. Their redox properties as well as molecular and crystal structures are affected by the alkyl substituents on the amino nitrogen and/or by the chalcogen atom (O, S, Se) in the heterocycle.