(1H-indol-3-yl)(p-tolyl)methanol | 944686-02-6

• 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: (1H-indol-3-yl)(p-tolyl)methanol
• 英文别名: 1H-indol-3-yl-(4-methylphenyl)methanol
• CAS: 944686-02-6
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: SLFAVWMMVBOCNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  36.02
• 氢给体数：
  2.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1H-indol-3-yl)(p-tolyl)methanol 在 二氢吡啶 、 对甲苯磺酸 作用下， 以 氯仿 为溶剂， 反应 0.08h， 以92%的产率得到3-(4-methylbenzyl)-1H-indole
  参考文献：
  名称：

  通过无金属转移氢化制取C-3烷基取代的吲哚的高效途径

  摘要：

  开发了通过3-吲哚甲醇的完全无金属催化转移加氢制取C-3烷基取代的吲哚的高效途径。该过程是通过在布朗斯台德酸的存在下原位形成的乙烯基亚胺基中间体进行的，汉茨酯用作还原剂。在较大的基材范围内，还原效果非常好，几乎在所有情况下，成品率均超过90％。

  DOI：

  10.1016/j.tetlet.2014.05.064
• 作为产物：
  描述：

  (1H-吲哚-3-基)-对甲苯-甲酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (1H-indol-3-yl)(p-tolyl)methanol
  参考文献：
  名称：

  Synthesis, Structure and Studies of Meso ‐Triaryl 22‐Oxabenzonorroles

  摘要：

  AbstractThe first examples of meso‐triaryl 22‐oxabenzonorroles were synthesized in 18–21% yields by oxidation of appropriate meso‐triaryl oxabenzobilane. The key precursors, the meso‐triaryl oxabenzobilanes were synthesized readily by treating 16‐oxatripyrrane with (1H‐indol‐3‐yl)(p‐tolyl)methanol under acid catalyzed conditions. The meso‐triaryl 22‐oxabenzonorroles were obtained in free base form by following our simple straight‐forward synthetic strategy. The X‐ray structure obtained for meso‐tritolyl 22‐oxabenzonorroles revealed that the indole ring was deviated by an angle of 41.27° from the mean plane. The NMR studies supported the presence of diatropic ring current effect as inner NH and CH protons were observed in the upfield region. The absorption spectra of 22‐oxabenzonorroles exhibited one strong Soret band and four weak Q‐bands. The electrochemical studies revealed that the macrocycles are electron rich and undergo easier oxidations. The DFT and TD‐DFT studies were in agreement with the experimental observations and NICS and HOMA values supports the aromatic nature of meso‐triaryl oxabenzonorroles.

  DOI：

  10.1002/asia.202200744

文献信息

• 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。
• Silica Gel Mediated Friedel–Crafts Alkylation of 3‐Indolylmethanols with Indoles: Synthesis of Unsymmetrical Bis(3‐indolyl)methanes
  作者：Yongzhen Zou、Cuili Chen、Xianxiao Chen、Xiaoxiang Zhang、Weidong Rao

  DOI：10.1002/ejoc.201700088

  日期：2017.4.26

  An efficient and expedient approach for the synthesis of unsymmetrical 3,3′-Bis-indolylmethanes via silica gel-mediated Friedel-Crafts alkylation of 3-indolylmethanols with diverse indoles is described. The synthetic utility of this transformation was demonstrated by reusing silica gel up to 10 times without apparent loss of reactivity .

  描述了通过硅胶介导的具有不同吲哚的 3-吲哚甲醇的 Friedel-Crafts 烷基化合成不对称 3,3'-双-吲哚甲烷的有效和方便的方法。通过重复使用硅胶 10 次而没有明显的反应性损失，证明了这种转化的合成效用。
• The Direct Asymmetric Alkylation of α-Amino Aldehydes with 3-Indolylmethanols by Enamine Catalysis
  作者：Zhi-Lei Guo、Jia-Hui Xue、Li-Na Fu、Shun-En Zhang、Qi-Xiang Guo

  DOI：10.1021/ol503318c

  日期：2014.12.19

  This work describes an efficient α-alkylation reaction of α-amino aldehydes with 3-indolylmethanols. In the promotion of catalyst 3f, the target products were obtained in high yields (up to 99%), good diastereoselectivities (up to 88:12), and excellent enantioselectivities (up to 96% ee). The direct alkylation products can be readily converted into other tryptophan derivatives without the loss of stereoselectivities

  这项工作描述了α-氨基醛与3-吲哚基甲醇的有效α-烷基化反应。在促进催化剂3f中，以高收率（最高99％），良好的非对映选择性（最高88:12）和优异的对映选择性（最高96％ee）获得目标产物。直接烷基化产物可以容易地转化为其他色氨酸衍生物，而不会失去立体选择性。
• Multifold C–C Coupling and Unorthodox Cyclization Catalysis for Selective Synthesis of Indolotriarylmethanes, Indolocarbazoles, and Their Analogues: A Control Experiment Study
  作者：Tuluma Das、Sudipto Debnath、Rituparna Maiti、Dilip K. Maiti

  DOI：10.1021/acs.joc.6b02689

  日期：2017.1.6

  The selective construction of medicinally and synthetically important indole-based unsymmetrical triarylmethanes using indoles and aldehydes is challenging because the significant nucleophilicity of indole leads to C–C coupling with an azafulvene intermediate to build up the alternative bis(indolyl)methane products, which may be useful synthons. A new, straightforward, ligand-free CuII catalytic strategy

  使用吲哚和醛选择性构建具有医学和合成意义的重要的基于吲哚的不对称三芳基甲烷是具有挑战性的，因为吲哚的显着亲核性会导致氮杂富烯中间体与C-C偶联，从而形成替代的双（吲哚基）甲烷产物。有用的合成子。新型，直接，无配体的Cu II通过将包括醛，吲哚和芳基硼酸的三个反应伙伴进行组装的双重C–C偶联，建立了不对称的吲哚三芳基甲烷和新的双吲哚基苯甲酰基类似物易于合成的催化策略。更重要的是，在有机碱和空中分子氧作为化学计量氧化剂的情况下，使用对称的双吲哚基苯甲酰基甲烷，利用CC裂解进行CC裂解的多重CC偶联环化反应，开发了这种方法。与简单的环缩合物吲哚并咔唑的形成相反，它经历了空前的选择性假四组分串联氧化环化反应，并由1,3-二羰基化合物裂解生成有价值的稠合5,7-二氢吲哚[2,3- b]。通过活性亚甲基残基的两个吲哚C（sp 2）–H和一个C（sp 3）–H键的官能化来合成]咔唑。为了更好地理解新反应