(S)-3-(1H-indol-3-yl)-butanal

• 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: (S)-3-(1H-indol-3-yl)-butanal
• 英文别名: (3S)-3-(1H-indol-3-yl)butanal
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: MLGJCWGLXXAKQX-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-3-(1H-indol-3-yl)-butanal 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 3-(1H-indol-3-yl)butan-1-ol
  参考文献：
  名称：

  α，β-不饱和醛对吲哚的高效不对称有机催化弗里德-克拉夫茨烷基化†

  摘要：

  有人提出了一种改进的有机催化剂，N-异丙基联吡咯烷2a，用于α，β-不饱和醛与吲哚的不对称Friedel-Crafts烷基化反应。新的有机催化剂很容易促进对映选择性烷基化反应，仅使用2摩尔％的催化剂负载量，即可以高至高收率（80-93％ee）提供高至高收率（62-89％）的3-烷基化的吲哚。

  DOI：

  10.1039/c0ob00016g
• 作为产物：
  描述：

  吲哚 、 巴豆醛 在 三氟甲磺酸 、 (2S,2'S,3R,3'R)-3,3'-bis(benzyloxy)-1-isopropyl-2,2'-bipyrrolidine 作用下， 以 甲醇 为溶剂， 反应 36.17h， 生成 (R)-3-(1H-indol-3-yl)-butanal 、 (S)-3-(1H-indol-3-yl)-butanal
  参考文献：
  名称：

  α，β-不饱和醛对吲哚的高效不对称有机催化弗里德-克拉夫茨烷基化†

  摘要：

  有人提出了一种改进的有机催化剂，N-异丙基联吡咯烷2a，用于α，β-不饱和醛与吲哚的不对称Friedel-Crafts烷基化反应。新的有机催化剂很容易促进对映选择性烷基化反应，仅使用2摩尔％的催化剂负载量，即可以高至高收率（80-93％ee）提供高至高收率（62-89％）的3-烷基化的吲哚。

  DOI：

  10.1039/c0ob00016g

文献信息

• Enantioselective Organocatalytic Indole Alkylations. Design of a New and Highly Effective Chiral Amine for Iminium Catalysis
  作者：Joel F. Austin、David W. C. MacMillan

  DOI：10.1021/ja017255c

  日期：2002.2.1

  "privileged" structure with representation in over 3000 natural isolates and 40 medicinal agents of diverse therapeutic action. A new strategy for asymmetric access to this important pharmacaphore has been accomplished that involves the amine catalyzed alkylation of indoles with alpha,beta-unsaturated aldehydes. Central to these studies has been the design of a new chiral amine catalyst that exhibits

  吲哚骨架已被广泛认为是一种“特权”结构，在超过 3000 种天然分离株和 40 种具有不同治疗作用的药物中具有代表性。已经完成了一种不对称访问这种重要药理学的新策略，该策略涉及胺催化的吲哚与 α、β-不饱和醛的烷基化。这些研究的核心是设计一种新的手性胺催化剂，该催化剂对亚胺催化具有更高的反应性和选择性。这种新型 (2S,5S)-5-苄基-2-叔丁基-咪唑啉酮催化剂能够以高产率和优异水平将多种吲哚体系共轭加成到多种 α,β-不饱和醛中对映控制（70-97% 产率，84-97% ee）。
• Enantioselective Friedel‐Crafts Alkylation of Indoles with  <i>α, β</i> ‐Unsaturated Aldehydes Catalyzed by Recyclable Second‐generation MacMillan Catalysts
  作者：Mohd Jubair Aalam、Deepa、Surendra Singh

  DOI：10.1002/ejoc.202200978

  日期：2022.11.18

  An efficient protocol for enantioselective Friedel-Crafts alkylation reaction was develoved using recoverable second-generation MacMillan catalysts in the presence of trifluoroacetic acid as a co-catalyst.

  在三氟乙酸作为助催化剂的情况下，使用可回收的第二代 MacMillan 催化剂开发了一种有效的对映选择性 Friedel-Crafts 烷基化反应方案。
• Enantioselective Friedel–Crafts alkylations catalysed by well-defined iridium and rhodium half-sandwich complexes
  作者：Daniel Carmona、María Pilar Lamata、Antonio Sánchez、Fernando Viguri、Luis A. Oro

  DOI：10.1016/j.tetasy.2011.05.003

  日期：2011.4

  Aqua-complexes (S-M,R-C)-[C-p*M((R)-prophos)(H2O)][SbF6](2)(M = Rh 1, Ir 2) catalysed the alkylation of alpha,beta-unsaturated aldehydes with aromatics and heteroaromatics but in some cases, mixtures of products were obtained. Complexes 1 and 2 were also used to activate nitroalkenes for the Friedel-Crafts alkylation of a variety of aromatics and heteroaromatics, in particular, 1,3,5-trimethoxybenzene. For this substrate, the monoalkylated adduct was obtained in quantitative yield with enantioselectivities of up to 73% ee being achieved. The intermediate catalyst/nitroalkene was isolated and characterized and the complex catalyst/adduct was detected spectroscopically. From these data a plausible catalytic cycle is proposed. (C) 2011 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of a Highly Potent Selective Serotonin Reuptake Inhibitor. An Application of Imidazolidinone Catalysis to the Alkylation of Indoles with an α,β-Disubstituted α,β-Unsaturated Aldehyde
  作者：H. Dalton King、Zhaoxing Meng、Derek Denhart、Ronald Mattson、Roy Kimura、Dedong Wu、Qi Gao、John E. Macor

  DOI：10.1021/ol051000c

  日期：2005.8.1

  [GRAPHICS]The synthesis of the highly potent and selective serotonin reuptake inhibitor 1 (BMS-594726) is described. In the key construction step, an enantioselective alkylation of the indole nucleus with an a-branched alpha,beta-unsaturated aldehyde 7 was accomplished utilizing MacMillan's imidazolidinone catalyst 3b. A rationale is presented for the unexpected stereochemical result, as well as the novel reactivity of the alpha-branched substrate.
• An Efficient Enantioselective Method for Asymmetric Friedel-Crafts Alkylation of Indoles with α,β-Unsaturated Aldehydes
  作者：Liang Hong、Lei Wang、Chao Chen、Bangzhi Zhang、Rui Wang

  DOI：10.1002/adsc.200800710

  日期：2009.3

  Abstractmagnified imageThe Lewis base‐Lewis base bifunctional catalytic system has been developed and successfully applied to the asymmetric Friedel–Crafts alkylation of indoles with α,β‐unsaturated aldehydes. The reactions are promoted by chiral diphenylprolinol trimethylsilyl ether in the presence of triethylamine. By this protocol, optically active 3‐substituted indoles can be obtained in an organocatalytic process that is free of Lewis or protic acid in high yields with up to 98% ee. Besides, this reaction could be carried out on a gram scale without any loss in the enantioselectivity.