tert-butyl (4,4-dibutoxycyclohexa-2,5-dien-1-ylidene)carbamate | 1613485-27-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: tert-butyl (4,4-dibutoxycyclohexa-2,5-dien-1-ylidene)carbamate
• CAS: 1613485-27-0
• 化学式: C₁₉H₃₁NO₄
• 分子量: 337.459
• InChiKey: NTPFIZWBBSTOBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  57.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3-二甲基吲哚 、 tert-butyl (4,4-dibutoxycyclohexa-2,5-dien-1-ylidene)carbamate 在 (11bS)-4-羟基-2,6-二[2,4,6-三(异丙基)苯基]-二萘并[2,1-d:1',2'-f][1,3,2]二氧杂磷杂卓4-氧化物 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以81%的产率得到tert-butyl (S)-(4-butoxy-3-(2,3-dimethyl-3H-indol-3-yl)phenyl)carbamate
  参考文献：
  名称：

  通过串联反应实现的2,3-二取代的吲哚的有机催化不对称芳香脱芳香化

  摘要：

  吲哚的有机催化不对称芳基脱芳香化反应是通过涉及2，3-二取代的吲哚和醌亚胺缩酮的两种串联方法实现的。一种方法利用对映选择性级联1,4加成/消除醇的反应，另一种方法采用单锅串联芳基化脱芳香化/转移氢化序列。在这两种情况下，均以高收率和出色的立体选择性（所有dr> 95：5，最高99％ee）生成带有全碳四元立体异构中心的对映异构体纯的吲哚衍生物 。

  DOI：

  10.1002/anie.201408551

文献信息

• Catalytic asymmetric chemodivergent arylative dearomatization of tryptophols
  作者：Chun Ma、Ting Zhang、Jia-Yu Zhou、Guang-Jian Mei、Feng Shi

  DOI：10.1039/c7cc06547g

  日期：——

  The first catalytic asymmetric arylative dearomatization of tryptophols has been established. By using quinone imine ketals as aryl group surrogates and modulating the reaction conditions, the cascade reaction of tryptophols with quinone imine ketals in the presence of chiral phosphoric acid afforded two series of arylative dearomatization products with generally high yields (up to 99%), excellent

  已经建立了对三酚的第一个催化不对称芳基脱芳香化反应。通过使用醌亚胺缩酮作为芳基替代物并调节反应条件，在手性磷酸存在下，三苯酚与醌亚胺缩酮的级联反应提供了两个系列的芳基脱芳香化产品，收率通常很高（高达99％），非常好非对映选择性和对映选择性（所有> 95：5 dr，90％至99％ee）以化学选择性方式进行。
• Organocatalytic Chemo- and Regioselective Oxyarylation of Styrenes via a Cascade Reaction: Remote Activation of Hydroxyl Groups
  作者：Yu-Chen Zhang、Fei Jiang、Shu-Liang Wang、Feng Shi、Shu-Jiang Tu

  DOI：10.1021/jo500859b

  日期：2014.7.3

  The first organocatalytic oxyarylation of styrenes has been established through a cascade of vinylogous Michael adclition/alkoxyl transfer reactions of o- or p-hydroxylstyrenes with quinone imine ketals. The process leads to a highly chemo- and regioselective oxyarylation of styrenes and provides access to m-alkylated anilines in generally high yields and excellent diastereoselectivity (up to 99% yield, >95:5 dr). An investigation of the reaction pathway revealed that the existence and position of the hydroxyl group of styrene played crucial roles in the cascade reaction, suggesting that the two reactants were simultaneously activated by binaphthyl-derived phosphoric acid via hydrogen bonding interactions and long-distance conjugative effects. In addition, the activating group of the hydroxyl functionality in the products can be easily removed or transformed, demonstrating the applicability and utility of this strategy in styrene oxyarylation and in the synthesis of styrene-based compounds.