2-(2-Methyl-2,3-dihydroinden-1-ylidene)propanedinitrile | 1046786-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(2-Methyl-2,3-dihydroinden-1-ylidene)propanedinitrile
• CAS: 1046786-28-0
• 化学式: C₁₃H₁₀N₂
• 分子量: 194.236
• InChiKey: OIFMSXCFHNIPHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-Methyl-2,3-dihydroinden-1-ylidene)propanedinitrile 、 2-cyclopropyl-1-benzenesulfonyldifluoromethylbenzo[b]thiophenium triflate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 0.75h， 以52%的产率得到
  参考文献：
  名称：

  S-（（苯磺酰基）二氟甲基）噻吩盐：β-酮酸酯，β-二酮和二氰基亚烷基的碳选择性亲电二氟甲基化

  摘要：

  S -（（苯磺酰基）二氟甲基）噻吩盐是通过三氟甲磺酸催化邻乙炔基芳基二氟甲基硫烷的分子内环化反应而设计和制备的。发现噻吩盐作为将CF 2 H基团引入sp 3杂交的碳亲核试剂（如β-酮酸酯和二氰基亚烷基）的亲电子二氟甲基化试剂非常有效。的（苯磺酰基）二氟甲基可容易地转化为CF 2温和反应条件下小时。在双（金鸡纳）生物碱的存在下也实现了对映选择性亲电二氟甲基化。

  DOI：

  10.1002/anie.201309875

文献信息

• Efficient Access to Extended Yagupolskii-Umemoto-Type Reagents: Triflic Acid Catalyzed Intramolecular Cyclization of ortho-Ethynylaryltrifluoromethylsulfanes
  作者：Andrej Matsnev、Shun Noritake、Yoshinori Nomura、Etsuko Tokunaga、Shuichi Nakamura、Norio Shibata

  DOI：10.1002/anie.200905225

  日期：2010.1.12

  King of the ring: S‐(trifluoromethyl)benzo[b]thiophenium salts 1, as analogues of Yagupolskii–Umemoto type reagents, were synthesized by novel triflic acid catalyzed intramolecular cyclization of ortho‐ethynylaryltrifluoromethylsulfanes 2. 1 j is especially useful for the electrophilic trifluoromethylation of β‐ketoesters and dicyanoalkylidenes.

  环中之王：S-（三氟甲基）苯并[b]噻吩盐1作为Yagupolskii–Umemoto型试剂的类似物，是通过新颖的三氟甲磺酸催化的邻乙炔基芳基三氟甲基硫烷2的分子内环化反应合成的。1 j对于亲电性特别有用β-酮酸酯和二氰基亚烷基的三氟甲基化。
• Fluorinated Johnson Reagent for Transfer-Trifluoromethylation to Carbon Nucleophiles
  作者：Shun Noritake、Norio Shibata、Shuichi Nakamura、Takeshi Toru、Motoo Shiro

  DOI：10.1002/ejoc.200800419

  日期：2008.7

  A novel reagent, [(oxido)phenyl(trifluoromethyl)-λ4-sulfanylidene]dimethylammonium tetrafluoroborate has been developed for the electrophilic trifluoromethylation of carbon nucleophiles. The reagent was designed as a trifluorinated version of a Johnson-type methyl-transfer reagent. The firstexample of vinylogous trifluoromethylation of dicyanoalkylidenes is also demonstrated.(© Wiley-VCH Verlag GmbH

  一种新型试剂[(氧化)苯基(三氟甲基)-λ4-亚硫基]二甲基四氟硼酸铵已被开发用于碳亲核试剂的亲电三氟甲基化。该试剂被设计为约翰逊型甲基转移试剂的三氟化版本。还展示了二氰基亚烷基的乙烯基三氟甲基化的第一个例子。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• TRIFLUOROMETHYLTHIOPHENIUM DERIVATIVE SALT, METHOD FOR PRODUCING THE SAME, AND METHOD FOR PRODUCING TRIFLUOROMETHYL-CONTAINING COMPOUNDS USING THE SAME
  申请人：Shibata Norio

  公开号：US20120130090A1

  公开（公告）日：2012-05-24

  A trifluoromethylthiophenium derivative salt useful as synthetic intermediates for pharmaceuticals and agrochemicals, a method for producing the same, and a method for producing trifluoromethyl-containing compounds using the same are provided. An S-(trifluoromethyl)-benzo[b]thiophenium derivative salt is represented by the following general formula (1): wherein R 1 , R 2 , R 3 , and R 4 are each independently a hydrogen atom, a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a methoxy group, an ethoxy group, a linear, branched, or cyclic alkyloxy group having 3 to 10 carbon atoms, a fluorine atom, a chlorine atom, a bromine atom, a nitro group, or a cyano group, R 5 is a methyl group, an ethyl group, a linear, branched, or cyclic alkyl group having 3 to 10 carbon atoms, a phenyl group, or a substituted phenyl group, and X − represents an anion. Various trifluoromethyl-containing compounds are produced using a method for producing the S-(trifluoromethyl)-benzo[b]thiophenium derivative salt, and using the S-(trifluoromethyl)-benzo[b]thiophenium derivative salt as a trifluoromethylating agent.

  本发明提供一种三氟甲基噻吩盐衍生物，可用作制药和农药的合成中间体，以及其制备方法和使用该盐衍生物制备含三氟甲基化合物的方法。S-(三氟甲基)-苯并[b]噻吩盐衍生物由下列普通式（1）表示：其中，R1、R2、R3和R4各自独立地是氢原子、甲基基团、乙基基团、具有3至10个碳原子的线性、支链或环烷基基团、甲氧基基团、乙氧基基团、具有3至10个碳原子的线性、支链或环烷氧基基团、氟原子、氯原子、溴原子、硝基或氰基，R5是甲基基团、乙基基团、具有3至10个碳原子的线性、支链或环烷基基团、苯基或取代苯基，X-表示阴离子。使用制备S-(三氟甲基)-苯并[b]噻吩盐衍生物的方法以及使用S-(三氟甲基)-苯并[b]噻吩盐衍生物作为三氟甲基化试剂可以制备各种三氟甲基含量的化合物。
• NONLINEAR OPTICAL MATERIAL COMPOSITION AND METHOD OF MANUFACTURE
  申请人：Yamamoto Michiharu

  公开号：US20100152338A1

  公开（公告）日：2010-06-17

  Embodiments of the present disclosure provide non-linear optical compounds and compositions comprising a silole-derivative. In an embodiment, the silole derivative comprises a chromophore including a structure represented by Formula (A): wherein each Of R 1 , R 2 , R 3 , and R 4 are independently selected from the group consisting of a hydrogen atom, a C 1-10 linear alkyl group, a C 1-10 branched alkyl group, a C 5-10 aryl group, a heteroaryl group, an alkene group, an alkyne group, a cycloalkene, a cycloalkyne, and a substituted or unsubstituted heteroatom and X 1 and X 2 are each independently selected from the group consisting of O, S, and Se. Compositions formed from embodiments of the silole derivative may be used in non-linear optical devices, particularly passive and active optical waveguides.
• [EN] NONLINEAR OPTICAL MATERIAL COMPOSITION AND METHOD OF MANUFACTURE<br/>[FR] COMPOSITION DE MATÉRIAU OPTIQUE NON LINÉAIRE ET PROCÉDÉ DE FABRICATION
  申请人：NITTO DENKO CORP

  公开号：WO2008109701A1

  公开（公告）日：2008-09-12

  [EN] Embodiments of the present disclosure provide non-linear optical compounds and compositions comprising a silole-derivative. In an embodiment, the silole derivative comprises a chromophore including a structure represented by Formula (A): wherein each Of R₁, R₂, R₃, and R₄ are independently selected from the group consisting of a hydrogen atom, a C_1-10 linear alkyl group, a C_1-10 branched alkyl group, a C_5-10 aryl group, a heteroaryl group, an alkene group, an alkyne group, a cycloalkene, a cycloalkyne, and a substituted or unsubstituted heteroatom and X₁ and X₂ are each independently selected from the group consisting of O, S, and Se. Compositions formed from embodiments of the silole derivative may be used in non-linear optical devices, particularly passive and active optical waveguides.
  [FR] L'invention concerne des composés optiques non linéaires et des compositions comprenant un dérivé de silole. Dans un mode de réalisation, le dérivé de silole comprend un chromophore comprenant une structure représentée par la formule (A) : dans laquelle chacun de R¹, R², R³ et R⁴ est indépendamment choisi dans le groupe constitué d'un atome d'hydrogène, d'un groupe alkyle linéaire en C₁ à ₁₀, d'un groupe alkyle ramifié en C_{1 à 10}, d'un groupe aryle en C_{5 à 10}, d'un groupe hétéroaryle, d'un groupe alcène, d'un groupe alcyne, d'un groupe cycloalcène, d'un groupe cycloalcyne et d'un hétéroatome substitué ou non substitué et X₁ et X₂ sont chacun indépendamment choisis dans le groupe constitué de O, S et Se. Des compositions formées à partir des modes de réalisation du dérivé de silole peuvent être utilisées dans des dispositifs optiques non linéaires, en particulier des guides d'onde optiques passifs et actifs.