1-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]-6-chloro-3-(prop-1-en-2-yl)-1H-indole | 1374605-97-6

• 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: 1-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]-6-chloro-3-(prop-1-en-2-yl)-1H-indole
• 英文别名: Tert-butyl 2-[tert-butyl(dimethyl)silyl]oxy-6-chloro-3-prop-1-en-2-ylindole-1-carboxylate
• CAS: 1374605-97-6
• 化学式: C₂₂H₃₂ClNO₃Si
• 分子量: 422.039
• InChiKey: WUDVYFVDLKPNGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]-6-chloro-3-(prop-1-en-2-yl)-1H-indole 、 di-tert-butyl (phenylmethylene)dicarbamate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以55%的产率得到(Z)-1-(tert-butoxycarbonyl)-3-(4-tert-butoxycarbonylamino-4-phenylbutan-2-ylidene)-6-chloroindolin-2-one
  参考文献：
  名称：

  3-Alkenyl-2-silyloxyindoles in Vinylogous Mannich Reactions: Synthesis of Aminated Indole-Based Scaffolds and Products

  摘要：

  The first Lewis acid catalyzed vinylogous Mukaiyama-type Mannich addition of 3-alkenyl-2-silyloxyindoles to in situ generated N-Boc imines has been established, which affords chiral alpha-alkylidene-delta-amino-2-oxindole products with good efficiency and complete gamma-site- and Z-selectivity. The reaction is wide in scope, as it can be applied with equal convenience to different silyloxyindole donors and aromatic or aliphatic aminal-derived aldimine acceptors. The utility of these scaffolds is demonstrated by their easy transformation into either spirocyclopropane oxindole,, or homotryptamine-like products, featuring nontraditional indole-based skeleton connections.

  DOI：

  10.1021/ol4036598
• 作为产物：
  描述：

  6-chloro-3-(propan-2-ylidene)indolin-2-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 1-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]-6-chloro-3-(prop-1-en-2-yl)-1H-indole
  参考文献：
  名称：

  3-Alkenyl-2-silyloxyindoles：一种使能但被低估的乙烯基碳亲核试剂的后代

  摘要：

  我们介绍了新型 3-alkenyl-2-silyloxyindole 亲核试剂，并通过开发前所未有的与芳香醛的乙烯基 Mukaiyama 型羟醛反应来证明它们的效用。该反应显示了出色的 γ 位点选择性和非对映选择性，并提供了在 C-3 位带有取代的环外双键的有价值的羟基化羟吲哚。进行了不对称催化版本的初步试验，它显示出对所需的乙烯醇醛产品有希望的对映选择性。

  DOI：

  10.1002/ejoc.201101446

文献信息

• Vinylogous Nucleophilic Substitution of the Hydroxy Group in Diarylmethanols with 3-Propenyl-2-silyloxyindoles: Towards the Synthesis of <i>α</i> -Alkylidene-<i>δ</i> -diaryl-2-oxindoles
  作者：Amol P. Jadhav、Amjad Ali、Ravi P. Singh

  DOI：10.1002/adsc.201601265

  日期：2017.5.2

  vinylogous substitution of the hydroxy group of diarylmethyl alcohols with 3‐alkenyl‐2‐silyloxyindoles, which affords broadly substituted α‐alkylidene‐δ‐diaryl‐2‐oxindole products with high efficiency and complete γ‐site and Z‐selectivity. The reaction displays very wide substrate scopes for both the reactants, benzhydryl alcohols and 3‐alkenyl‐2‐silyloxyindoles. The utility of the substituted adducts

  我们在此报告为二芳基醇的羟基基团的三氟甲磺酸铟催化插烯取代成3-链烯基-2- silyloxyindoles，一个高度立体选择性方法，该方法得到广泛地被取代的α -alkylidene- δ -diaryl -2-羟基吲哚产品具有高效率以及完整的γ位和Z选择性。对于反应物，二苯甲基醇和3-烯基-2-甲硅烷基氧基吲哚，反应显示出非常宽的底物范围。取代的加合物转化为其他有用的衍生物可显示其效用。
• 3-Alkenyl-2-silyloxyindoles: An Enabling, Yet Understated Progeny of Vinylogous Carbon Nucleophiles
  作者：Gloria Rassu、Vincenzo Zambrano、Rossella Tanca、Andrea Sartori、Lucia Battistini、Franca Zanardi、Claudio Curti、Giovanni Casiraghi

  DOI：10.1002/ejoc.201101446

  日期：2012.1

  We introduce novel 3-alkenyl-2-silyloxyindole nucleophiles and demonstrate their utility by developing an unprecedented vinylogous Mukaiyama-type aldol reaction with aromatic aldehydes. This reaction displays excellent levels of γ- site selectivity and diastereoselectivity and delivers valuable hydroxylated oxindoles bearing a substituted exocyclic double bond at the C-3 position. A preliminary trial

  我们介绍了新型 3-alkenyl-2-silyloxyindole 亲核试剂，并通过开发前所未有的与芳香醛的乙烯基 Mukaiyama 型羟醛反应来证明它们的效用。该反应显示了出色的 γ 位点选择性和非对映选择性，并提供了在 C-3 位带有取代的环外双键的有价值的羟基化羟吲哚。进行了不对称催化版本的初步试验，它显示出对所需的乙烯醇醛产品有希望的对映选择性。
• 3-Alkenyl-2-silyloxyindoles in Vinylogous Mannich Reactions: Synthesis of Aminated Indole-Based Scaffolds and Products
  作者：Beatrice Ranieri、Andrea Sartori、Claudio Curti、Lucia Battistini、Gloria Rassu、Giorgio Pelosi、Giovanni Casiraghi、Franca Zanardi

  DOI：10.1021/ol4036598

  日期：2014.2.7

  The first Lewis acid catalyzed vinylogous Mukaiyama-type Mannich addition of 3-alkenyl-2-silyloxyindoles to in situ generated N-Boc imines has been established, which affords chiral alpha-alkylidene-delta-amino-2-oxindole products with good efficiency and complete gamma-site- and Z-selectivity. The reaction is wide in scope, as it can be applied with equal convenience to different silyloxyindole donors and aromatic or aliphatic aminal-derived aldimine acceptors. The utility of these scaffolds is demonstrated by their easy transformation into either spirocyclopropane oxindole,, or homotryptamine-like products, featuring nontraditional indole-based skeleton connections.