4-benzyl-2-(3,4,5-trimethoxyphenyl)-4H-1,3-oxazol-5-one | 1072120-51-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-benzyl-2-(3,4,5-trimethoxyphenyl)-4H-1,3-oxazol-5-one
• CAS: 1072120-51-4
• 化学式: C₁₉H₁₉NO₅
• 分子量: 341.364
• InChiKey: HROGKRVOOUHCAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-benzyl-2-(3,4,5-trimethoxyphenyl)-4H-1,3-oxazol-5-one 、 1-ethynyl-1H,3H-oxazolo[3,4-a]indol-3-one 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 三乙胺 、 2,6-二[(4S)-4-苯基-2-恶唑啉基]吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以77%的产率得到N-((1S,2R)-2-benzyl-1-ethynyl-3-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-yl)-3,4,5-trimethoxybenzamide
  参考文献：
  名称：

  通过吲哚基铜-亚烯基中间体的催化不对称[3 + 2]环空反应：吡咯并[1,2-a]吲哚的非对映和对映选择性组装。

  摘要：

  通过吲哚基铜-亚烯基两亲中间体的催化不对称脱羧[3 + 2]环已得到开发。该协议为具有重要的非对映和对映选择性（高达> 20：1 dr和> 99％ee）的具有相邻季四级和三级立体生成中心的生物学上重要的吡咯并[1,2- a ]吲哚的合成提供了一种简单的方法。另外，吡咯并[1,2- a ]吲哚的多样性导向合成是通过含炔的环加合物的多用途转化而实现的。

  DOI：

  10.1021/acs.orglett.0c01594

文献信息

• Highly Stereoselective [4+2] Cycloaddition of Azlactones to β,γ-Unsaturated α-Ketoesters Catalyzed by an Axially Chiral Guanidine Base
  作者：Masahiro Terada、Hiroyuki Nii

  DOI：10.1002/chem.201003015

  日期：2011.2.7

  cycloaddition reaction of azlactones with β,γ‐unsaturated α‐ketoesters was demonstrated by taking advantage of the multiple reactive sites on the azlactone with the use of an axially chiral guanidine‐base catalyst. The most likely reaction pathway involves three consecutive steps to provide a facile access to α‐amino δ‐lactones with a sugar framework in a highly stereoselective manner (see scheme).

  甜蜜的催化！利用轴向手性胍基催化剂，通过利用氮杂内酯上的多个反应位点，证明了氮杂内酯与β，γ-不饱和α-酮酸酯的对映体和非对映选择性环加成反应。最可能的反应途径包括三个连续的步骤，以高度立体选择性的方式（使用方案）轻松获得带有糖骨架的α-氨基δ-内酯。
• Asymmetric synthesis of pyrrolo[1,2-a]indoles via organocatalytic [3 + 2] annulation of substituted 2-vinylindoles with azlactones
  作者：Wulin Yang、Hao Wang、Zirong Pan、Zhong Li、Weiping Deng

  DOI：10.1016/j.cclet.2019.09.008

  日期：2020.3

  Abstract The chiral phosphoric acid catalyzed asymmetric [3 + 2] annulation of substituted 2-vinylindoles with azlactones has been established. This reaction represented a practical approach for the synthesis of structurally diverse pyrrolo[1,2-a]indoles with two vicinal stereocenters including one tetrasubstituted stereocenter in good yields and good stereoselectivities under mild conditions.

  摘要建立了手性磷酸催化含氮内酯取代的2-乙烯基吲哚的不对称[3 + 2]环化反应。该反应代表了在温和条件下以良好的产率和良好的立体选择性合成具有两个邻位立体中心（包括一个四取代的立体中心）的结构多样的吡咯并[1,2-a]吲哚的实用方法。
• COAP-Pd Catalyzed Asymmetric Allylic Alkylation of Azlactones with MBH Carbonates: Access to Unnatural α-Quaternary Stereogenic Glutamic Acid Derivatives
  作者：Sheng-Suo Zhou、Xing-Yun Sun、Wen-Kai Liu、Jia-Yu Song、Zheng Wang、Zheng-Hang Qi、Xing-Wang Wang

  DOI：10.1021/acs.joc.3c01152

  日期：2023.8.18

  palladium-catalyzed regioselective and asymmetric allylic alkylation of azlactones with MBH carbonates has been developed with chiral oxalamide-phosphine ligands. The corresponding reaction afforded a range of optically active γ-arylidenyl glutamic acid derivatives bearing an α-chiral quaternary stereocenter in good yields with excellent linear regio- and high enantioselectivity. This protocol furnishes

  使用手性草酰胺-膦配体开发了钯催化二氢唑酮与 MBH 碳酸酯的区域选择性和不对称烯丙基烷基化反应。相应的反应以良好的收率提供了一系列带有α-手性季立体中心的光学活性γ-亚芳基谷氨酸衍生物，具有优异的线性区域选择性和高对映选择性。该方案为构建对映体富集的非天然 α-氨基酸衍生物提供了另一种方法。
• Chiral Tetraaminophosphonium Carboxylate-Catalyzed Direct Mannich-Type Reaction
  作者：Daisuke Uraguchi、Yusuke Ueki、Takashi Ooi

  DOI：10.1021/ja806311e

  日期：2008.10.29

  The cooperative asymmetric catalysis of chiral tetraaminophosphonium carboxylate (P,S)-1-OCOR has been established, and its synthetic utility has been successfully demonstrated by application to the highly enantioselective direct Mannich-type reaction of azlactones with N-sulfonyl imines. The present study stimulates the cultivation of the potential of the chiral quaternary onium salt catalysis by the structural modification of organic anion.
• Catalytic Asymmetric [3 + 2] Annulation via Indolyl Copper–Allenylidene Intermediates: Diastereo- and Enantioselective Assembly of Pyrrolo[1,2-<i>a</i>]indoles
  作者：Jian Zhang、Tao Ni、Wu-Lin Yang、Wei-Ping Deng

  DOI：10.1021/acs.orglett.0c01594

  日期：2020.6.5

  A catalytic asymmetric decarboxylative [3 + 2] annulation via indolyl copper–allenylidene amphiphilic intermediates has been developed. This protocol offers a straightforward method for the synthesis of biologically important pyrrolo[1,2-a]indoles bearing contiguous quaternary and tertiary stereogenic centers with excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). In addition

  通过吲哚基铜-亚烯基两亲中间体的催化不对称脱羧[3 + 2]环已得到开发。该协议为具有重要的非对映和对映选择性（高达> 20：1 dr和> 99％ee）的具有相邻季四级和三级立体生成中心的生物学上重要的吡咯并[1,2- a ]吲哚的合成提供了一种简单的方法。另外，吡咯并[1,2- a ]吲哚的多样性导向合成是通过含炔的环加合物的多用途转化而实现的。