phenyl(1-tosyl-1H-indol-3-yl)methanol | 222306-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl(1-tosyl-1H-indol-3-yl)methanol
• 英文别名: [1-(4-Methylphenyl)sulfonylindol-3-yl]-phenylmethanol
• CAS: 222306-45-8
• 化学式: C₂₂H₁₉NO₃S
• 分子量: 377.464
• InChiKey: UNYIGAIOXWNRRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  phenyl(1-tosyl-1H-indol-3-yl)methanol 在 N-氟代双苯磺酰胺 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以24%的产率得到3-fluoro-1-(4-toluenesulfonyl)indole
  参考文献：
  名称：

  烯丙基醇的氟化反应中的不同反应性：通过碳-碳键裂解合成Z-氟烯烃

  摘要：

  在无催化剂条件下使用N-氟苯磺酰亚胺（NFSI）可以诱导烯丙基醇中未应变的碳-碳键非常规断裂。通过使用这种简单的方法，可以从环状和无环烯丙基醇中以高收率和高选择性获得各种官能化的Z-氟代烯烃。

  DOI：

  10.1039/c7sc00483d
• 作为产物：
  描述：

  phenyl(1-tosyl-1H-indol-3-yl)methanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 phenyl(1-tosyl-1H-indol-3-yl)methanol
  参考文献：
  名称：

  New selective nonsteroidal aromatase inhibitors: Synthesis and inhibitory activity of 2,3 or 5-(α-azolylbenzyl)-1H-indoles

  摘要：

  Six azolyl substituted indoles were synthesized and tested for their activity to inhibit two P450 enzymes: P450 arom and P450 17 alpha. It was observed that the introduction of alpha-imidazolylbenzyl chain at carbon 3 or 5 on indole nucleus led to very active molecules. Compounds 22, 23 and especially 33 demonstrate very high potential against P450 arom. Under our assay conditions of high substrate concentration the IC50 are 0.057, 0.0785 and 0.041 mu M,respectively. These compounds are moderate inhibitors against P450 17 alpha. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00737-9

文献信息

• Reactivity of indole-3-alkoxides in the absence of acids: Rapid synthesis of homo-bisindolylmethanes
  作者：Bhavani Shankar Chinta、Beeraiah Baire

  DOI：10.1016/j.tet.2016.10.067

  日期：2016.12

  properties of the alkoxides offered the direct and selective construction of bisindolylmethanes and indole-3-carbinols. This process shows very broad scope and represents the reagent (external) free, greener synthesis of structurally divergent bisindolylmethanes.

  据报道，原位生成的吲哚-3-醇盐（MgX或Li）具有空前的行为。调节醇盐的电子性质可以直接和选择性地构建双吲哚甲烷和吲哚-3-甲醇。该方法显示出非常广泛的范围，并且代表了无试剂（外部），绿色发散的结构不同的双吲哚甲烷的合成。
• Direct Synthesis of Indanes via Iron-Catalyzed Dehydrative Coupling/Friedel-Crafts Cyclization of Two Different Alcohols
  作者：Masahiro Sai

  DOI：10.1002/ejoc.201801573

  日期：2019.2.7

  A novel iron‐catalyzed cascade dehydrative coupling/Friedel–Crafts cyclization of two different alcohols to indanes has been developed. This approach is highly atom‐economic and environmentally benign, as it employs readily available alcohols as substrates and generates only water as byproduct.

  已经开发出了一种新颖的铁催化级联脱水偶联/两种不同醇与茚满的弗里德-克拉夫茨环化反应。这种方法具有高度的原子经济性和环境友好性，因为它采用了现成的醇作为底物，并且仅产生水作为副产物。
• Fluorinated Alcohol-Mediated S_N1-Type Reaction of Indolyl Alcohols with Diverse Nucleophiles
  作者：Hao Wen、Liang Wang、Lubin Xu、Zhihui Hao、Chang-Lun Shao、Chang-Yun Wang、Jian Xiao

  DOI：10.1002/adsc.201500500

  日期：2015.12.14

  This paper describes an efficient SN1-type reaction of 3-indolylmethanols with miscellaneous nucleophiles, featuring a catalyst-free procedure, low cost, wide substrate scope and mild reaction conditions. This approach provides green and efficient methods for the synthesis of diverse 3-substituted indolyl derivatives as well as unsymmetrical bisindolylmethanes and triarylmethanes.

  本文介绍了3-吲哚甲醇与杂种亲核试剂的高效S N 1型反应，具有无催化剂操作，成本低，底物范围宽和反应条件温和的特点。这种方法为合成各种3-取代的吲哚基衍生物以及不对称的双吲哚基甲烷和三芳基甲烷提供了绿色有效的方法。
• Catalyst-free dehydrative S_N1-type reaction of indolyl alcohols with diverse nucleophiles “on water”
  作者：Jian Xiao、Hao Wen、Liang Wang、Lubin Xu、Zhihui Hao、Chang-Lun Shao、Chang-Yun Wang

  DOI：10.1039/c5gc01838b

  日期：——

  An efficient dehydrative S_N1-type reaction of indolyl alcohols with diverse nucleophiles was developed using water as the solvent, affording versatile 3-indolyl derivatives in high yields. The advantages of being catalyst-free, environmentally benign, and wide substrate scope make it a promising method for preparation of indolyl compounds.

  利用水作为溶剂，开发了一种高效的无催化剂的脱水性SN1型反应，可将吲哚醇与多样的亲核试剂反应，产率高，得到多功能的3-吲哚衍生物。无需催化剂、环境友好且底物范围广泛的优点使其成为制备吲哚化合物的一种有前景的方法。
• Tris(pentafluorophenyl)borane-Catalyzed Alkylation of 1,3-Dicarbonyl Compounds with Benzylic Alcohols: Access to Oxygenated Heterocycles
  作者：Chada Reddy、Jonnalagadda Vijaykumar、René Grée

  DOI：10.1055/s-0030-1258214

  日期：2010.11

  rane has found to be an effective catalyst for the alkylation of 1,3-dicarbonyl compounds using benzylic alcohols as alkylating agents. Various 1,3-dicarbonyl compounds reacted cleanly with different benzylic alcohols to provide the corresponding monoalkylated products in good yield. In addition tris(pentafluorophenyl)borane efficiently promoted the C3 alkylation of 4-hydroxycoumarins. Further, several

  已经发现三（五氟苯基）硼烷是使用苄醇作为烷基化剂将1，3-二羰基化合物烷基化的有效催化剂。各种1,3-二羰基化合物可与不同的苄醇干净地反应，以高收率提供相应的单烷基化产物。另外，三（五氟苯基）硼烷有效地促进了4-羟基香豆素的C3烷基化。此外，已经使用所述方法学作为关键步骤制备了几种氧化的杂环，例如呋喃，4 H-色烯和呋喃香豆素。 三（五氟苯基）硼烷-1,3-二羰基化合物-苄醇-烷基化-杂环