(C8H6N)CH(Ts)(4-Cl-C6H4) | 1190880-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (C8H6N)CH(Ts)(4-Cl-C6H4)
• 英文别名: 3-[(4-chlorophenyl)-(4-methylphenyl)sulfonylmethyl]-1H-indole
• CAS: 1190880-06-8
• 化学式: C₂₂H₁₈ClNO₂S
• 分子量: 395.909
• InChiKey: NHVBJHVGZKECDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (C8H6N)CH(Ts)(4-Cl-C6H4) 、 (乙氧基羰基甲基)二甲基溴化硫鎓 在 potassium carbonate 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 12.0h， 以81%的产率得到ethyl 3-(4-chlorophenyl)spiro[cyclopropane-1,3'-indole]-2-carboxylate
  参考文献：
  名称：

  The Concise Synthesis of Spiro-Cyclopropane Compounds via the Dearomatization of Indole Derivatives

  摘要：

  A concise synthesis of spiro-cyclopropane compounds from indole derivatives and sulfur ylides has been developed via a dearomatization strategy. Moreover, the spiro-cyclopropane compounds could be conveniently transformed to rearomatized indole derivatives in the presence of acids.

  DOI：

  10.1021/ol500948r
• 作为产物：
  描述：

  吲哚 、 ethyl N-[(4-chlorophenyl)(tosyl)methyl]carbamate 在 indium(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以83%的产率得到(C8H6N)CH(Ts)(4-Cl-C6H4)
  参考文献：
  名称：

  InBr 3：适用于不同类型的Friedel-Crafts反应的多功能催化剂

  摘要：

  在室温下，在CH 2 Cl 2中，已开发出温和有效的InBr 3催化的杂芳族或富电子芳族化合物与α-酰胺基砜的Friedel-Crafts烷基化反应。产物进一步与杂芳族或富电子芳族化合物进行弗里德-克拉夫特烷基化反应，从而以高收率得到不对称或双对称的三芳基甲烷。α-酰胺基砜被用于合成不对称和双对称的三芳基甲烷。使用温和的反应条件，低催化负荷和高收率是本方法的优点。

  DOI：

  10.1021/jo9014613

文献信息

• Catalyst-free synthesis of 3-(1-arylsulfonylalkyl)indoles via three-component reaction of indoles, carbonyls, and arenesulfinic acids
  作者：Wenzhong Huang、Juan Yang、Xiangguang Li、Lin Yuan、Yinhai Ma、Qinglong Zhou、Deqiang Liang

  DOI：10.1080/10426507.2015.1100182

  日期：2016.5.3

  ABSTRACT A catalyst-free three-component reaction of indoles, carbonyls, and arenesulfinic acids performed at room temperature provides direct access to biologically important 3-(1-arylsulfonylalkyl)indoles. This process features mild conditions, low cost, broad substrate scope, and high yields, and mechanistically bis(indolyl)methanes were identified as the key intermediates. GRAPHICAL ABSTRACT

  摘要 在室温下进行的吲哚、羰基化合物和芳烃亚磺酸的无催化剂三组分反应提供了直接获得生物学上重要的 3-（1-芳基磺酰基烷基）吲哚的途径。该工艺具有条件温和、成本低、底物适用范围广、收率高等特点，在机理上双（吲哚基）甲烷被确定为关键中间体。图形概要
• Highly diastereo- and enantioselective synthesis of syn-β-substituted tryptophans via asymmetric Michael addition of a chiral equivalent of nucleophilic glycine and sulfonylindoles
  作者：Jiang Wang、Shengbin Zhou、Daizong Lin、Xiao Ding、Hualiang Jiang、Hong Liu

  DOI：10.1039/c1cc12619a

  日期：——

  The asymmetric synthesis of syn-beta-substituted tryptophan derivatives was carried out by the Michael addition of chiral equivalent of nucleophilic glycine with sulfonylindoles, and high diastereo- and enantioselectivities were achieved. The resulting adducts were readily converted to syn-beta-substituted tryptophans in 96% yield, indicating that the proposed method is a highly efficient route to

  通过将亲核甘氨酸的手性当量与磺酰吲哚的迈克尔加成，进行了β-取代色氨酸衍生物的不对称合成，并获得了高非对映选择性和对映选择性。所得的加合物易于以96％的产率转化为合成β-取代的色氨酸，表明所提出的方法是制备手性合成β-取代的色氨酸的高效途径。
• Ag-Catalyzed Diastereo- and Enantioselective Synthesis of β-Substituted Tryptophans from Sulfonylindoles
  作者：Bao-Hui Zheng、Chang-Hua Ding、Xue-Long Hou、Li-Xin Dai

  DOI：10.1021/ol100161n

  日期：2010.4.16

  The asymmetric catalytic synthesis of beta-substituted tryptophan derivatives was realized in high diastereo- and enantioselectivity by the reaction of glycine derivatives with sulfonylindoles in the presence of catalyst derived from AgCl and a commercially available chiral monodentate phosphoramidite ligand. The resulting adduct was readily converted to beta-substituted tryptophan in 95% overall yield for two steps, which presented a highly efficient route to chiral beta-substituted tryptophan.
• InBr₃: A Versatile Catalyst for the Different Types of Friedel−Crafts Reactions
  作者：Ponnaboina Thirupathi、Sung Soo Kim

  DOI：10.1021/jo9014613

  日期：2009.10.16

  Mild and efficient InBr3-catalyzed Friedel−Crafts alkylation of heteroaromatic or electron-rich aromatic compounds with α-amido sulfones at room temperature in CH2Cl2 has been developed. The products undergo further Friedel−Crafts alkylation with heteroaromatic or electron-rich aromatic compounds leading to unsymmetrical or bis-symmetrical triaryl methanes in good yield. α-Amido sulfones are employed

  在室温下，在CH 2 Cl 2中，已开发出温和有效的InBr 3催化的杂芳族或富电子芳族化合物与α-酰胺基砜的Friedel-Crafts烷基化反应。产物进一步与杂芳族或富电子芳族化合物进行弗里德-克拉夫特烷基化反应，从而以高收率得到不对称或双对称的三芳基甲烷。α-酰胺基砜被用于合成不对称和双对称的三芳基甲烷。使用温和的反应条件，低催化负荷和高收率是本方法的优点。
• The Concise Synthesis of Spiro-Cyclopropane Compounds via the Dearomatization of Indole Derivatives
  作者：Jing Luo、Bo Wu、Mu-Wang Chen、Guo-Fang Jiang、Yong-Gui Zhou

  DOI：10.1021/ol500948r

  日期：2014.5.16

  A concise synthesis of spiro-cyclopropane compounds from indole derivatives and sulfur ylides has been developed via a dearomatization strategy. Moreover, the spiro-cyclopropane compounds could be conveniently transformed to rearomatized indole derivatives in the presence of acids.