3-(4-hydroxybenzyl)indole | 136672-21-4

• 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: 3-(4-hydroxybenzyl)indole
• 英文别名: 4-(1H-indol-3-ylmethyl)phenol
• CAS: 136672-21-4
• 化学式: C₁₅H₁₃NO
• 分子量: 223.274
• InChiKey: UFLSRBOSXIURIY-UHFFFAOYSA-N

物化性质

• 沸点：
  449.0±25.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  吲哚 、 对羟基苯甲醇 以 邻二甲苯 为溶剂， 反应 22.0h， 以75%的产率得到3-(4-hydroxybenzyl)indole
  参考文献：
  名称：

  可重复使用的Pt纳米簇催化剂将吲哚与伯醇进行常规和选择性C-3烷基化

  摘要：

  铂规则：异构，通过转移氢化的条件下进行与可重复使用的Pt /θ-Al系的脂肪族和芳族醇吲哚不含添加剂的C-3选择性烷基化2 ö 3催化剂（参见方案; TON =周转数）。

  DOI：

  10.1002/chem.201302464

文献信息

• CuI-Catalyzed Selective 3-Alkylation of Indoles with <i>N</i> -Tosylhydrazones and the I₂ -Mediated Further Cyclization to Chromeno[2,3-<i>b</i> ]Indoles
  作者：Chun-Bao Miao、Yan-Fang Sun、He Wu、Xiao-Qiang Sun、Hai-Tao Yang

  DOI：10.1002/adsc.201800206

  日期：2018.7.4

  The CuI‐catalyzed reaction of indoles with N‐tosylhydrazones derived from the ortho‐/para‐hydroxybenzaldhydes affords selectively the C‐3 alkylated products rather than the N‐alkylated products. In addition, the I2‐mediated cyclization of the generated C‐3 alkylated products allows the concise synthesis of chromeno[2,3‐b]indole derivatives.

  吲哚与碘化亚铜催化反应Ñ -tosylhydrazones从派生邻- /对-hydroxybenzaldhydes得到选择性地将Ç -3烷基化产物，而不是Ñ烷基化产品。此外，生成的C-3烷基化产物的I 2介导的环化反应可简化chromeno [2,3- b ]吲哚衍生物的合成。
• Molecular modeling parameters predict antioxidant efficacy of 3-indolyl compounds
  作者：H. G. Shertzer、M. Wilson Tabor、I. T. D. Hogan、Stephen J. Brown、Malcolm Sainsbury

  DOI：10.1007/s002040050346

  日期：1996.10.14

  Many dietary constituents, such as indole-3-carbinol, are chemoprotective in toxicity and carcinogenicity: bioassays, Indole-Li-carbinol and related congeners appear to prefect partly via radical and electrophile scavenging. To develop better chemoprotective indoles with lower intrinsic toxicity, we performed molecular graphic and quantum-mechanical analyses of model indolyl compounds to ascertain the determinant molecular features for antioxidant activity. We examined eight structurally related 3-indolyl compounds for relationships between antioxidation potential (using in vitro lipid peroxidation assays) and electronic, polar, and steric parameters, including bond dissociation energies, bond lengths, dipole moments, electronic charge densities, and molecular size parameters. Electronic features of the 3-methylene carbon and 1-nitrogen were not predictive of antioxidative potency due to extensive charge delocalization of the cation radical following electron abstraction from the nitrogen, Antioxidant efficacy of 3-indolyl compounds was most strongly predicted by molecular size parameters and by the energy of electron abstraction as calculated from the difference in heat of formation between the parent compound and its cation radical, A highly predictive multiple linear regression correlation model (r(2) = 0.97) was obtained using the parameters of heal of formation, molecular weight, log P, and diplole moment.
• PROCESSES AND HOST CELLS FOR GENOME, PATHWAY, AND BIOMOLECULAR ENGINEERING
  申请人：enEvolv, Inc.

  公开号：EP3027754A1

  公开（公告）日：2016-06-08
• [EN] PROCESSES AND HOST CELLS FOR GENOME, PATHWAY, AND BIOMOLECULAR ENGINEERING<br/>[FR] PROCÉDÉS ET CELLULES HÔTES POUR INGÉNIERIE BIOMOLÉCULAIRE, GÉNOMIQUE ET DE LA VOIE
  申请人：ENEVOLV INC

  公开号：WO2015017866A1

  公开（公告）日：2015-02-05

  The present disclosure provides compositions and methods for genomic engineering.
• General and Selective C-3 Alkylation of Indoles with Primary Alcohols by a Reusable Pt Nanocluster Catalyst
  作者：S. M. A. Hakim Siddiki、Kenichi Kon、Ken-ichi Shimizu

  DOI：10.1002/chem.201302464

  日期：2013.10.18

  The platinum rule: Heterogeneous, additive‐free C‐3 selective alkylation of indoles by aliphatic and aromatic alcohols proceeded under transfer hydrogenation conditions with the reusable Pt/θ‐Al2O3 catalyst (see scheme; TON=turnover number).

  铂规则：异构，通过转移氢化的条件下进行与可重复使用的Pt /θ-Al系的脂肪族和芳族醇吲哚不含添加剂的C-3选择性烷基化2 ö 3催化剂（参见方案; TON =周转数）。