(2,4-dichlorophenyl)(1H-indol-3-yl)methanol | 1554540-95-2

• 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: (2,4-dichlorophenyl)(1H-indol-3-yl)methanol
• CAS: 1554540-95-2
• 化学式: C₁₅H₁₁Cl₂NO
• 分子量: 292.164
• InChiKey: PTBPBXCPNDFTGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (2,4-dichlorophenyl)(1H-indol-3-yl)methanol 在 咪唑 、 C₇₂H₄₅NO₆P₂ 作用下， 以 四氢呋喃 为溶剂， 反应 72.5h， 生成
  参考文献：
  名称：

  Enantioselective Synthesis of Triarylmethanes by Chiral Imidodiphosphoric Acids Catalyzed Friedel–Crafts Reactions

  摘要：

  The first enantioselective synthesis of pyrrolyl-substituted triarylmethanes has been accomplished using a novel imidodiphosphoric acid catalyst, which is derived from two (R)BINOL frameworks with different 3,3'-substituents. This strategy was also expanded to the synthesis of bis(indolyl)-substituted triarylmethanes with high enantioselectivities, which could only be obtained with moderate ee values in previous reports. These two efficient Friedel-Crafts alkylation processes feature low catalyst loading, broad functional group compatibilities, and the potential to provide practical pathways for the synthesis of enantioenriched bioactive triarylmethanes.

  DOI：

  10.1021/ol403680c
• 作为产物：
  描述：

  吲哚 、 2,4-二氯苯甲醛 在 四甲基胍 作用下， 以 水 为溶剂， 反应 24.0h， 生成 (2,4-dichlorophenyl)(1H-indol-3-yl)methanol
  参考文献：
  名称：

  Enantioselective Synthesis of Triarylmethanes by Chiral Imidodiphosphoric Acids Catalyzed Friedel–Crafts Reactions

  摘要：

  The first enantioselective synthesis of pyrrolyl-substituted triarylmethanes has been accomplished using a novel imidodiphosphoric acid catalyst, which is derived from two (R)BINOL frameworks with different 3,3'-substituents. This strategy was also expanded to the synthesis of bis(indolyl)-substituted triarylmethanes with high enantioselectivities, which could only be obtained with moderate ee values in previous reports. These two efficient Friedel-Crafts alkylation processes feature low catalyst loading, broad functional group compatibilities, and the potential to provide practical pathways for the synthesis of enantioenriched bioactive triarylmethanes.

  DOI：

  10.1021/ol403680c

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。
• Fluorinated alcohol-mediated [4 + 3] cycloaddition reaction of indolyl alcohols with cyclopentadiene
  作者：Jian Liu、Liang Wang、Xiaoxiao Wang、Lubin Xu、Zhihui Hao、Jian Xiao

  DOI：10.1039/c6ob01953f

  日期：——

  + 3] cycloaddition reaction of 3-indolylmethanols with cyclopentadiene in hexafluoroisopropanol (HFIP), which is catalyst-free and inexpensive, and offers mild reaction conditions, wide substrate scope and convenient workup. This methodology provides the first catalyst- and additive-free [4 + 3] cycloaddition reactions of indolyl alcohols, offering a green and efficient method for the synthesis of cyclohepta[b]indole

  本文介绍了3-吲哚基甲醇与环戊二烯在六氟异丙醇（HFIP）中的高效[4 + 3]环加成反应，该反应无催化剂且价格低廉，并且提供了温和的反应条件，宽泛的底物范围和方便的后处理方法。该方法学提供了吲哚醇的第一个无催化剂和无添加剂的[4 + 3]环加成反应，为合成环庚[ b ]吲哚衍生物提供了一种绿色而有效的方法。