tert-butyl 3-(but-3-en-1-yl)-3-hydroxyazetidine-1-carboxylate | 1446012-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: tert-butyl 3-(but-3-en-1-yl)-3-hydroxyazetidine-1-carboxylate
• 英文别名: tert-Butyl 3-(but-3-enyl)-3-hydroxyazetidine-1-carboxylate；tert-butyl 3-but-3-enyl-3-hydroxyazetidine-1-carboxylate
• CAS: 1446012-46-9
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: BEBZYARESSLCRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(but-3-en-1-yl)-3-hydroxyazetidine-1-carboxylate 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 碘 、 sodium ethanolate 、 碳酸氢钠 作用下， 以 乙醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 1.0h， 生成 2-[(tert-butoxy)carbonyl]-5-oxa-2-azaspiro[3.4]octane-6-carboxylic acid
  参考文献：
  名称：

  Oxa-spirocycles: synthesis, properties and applications

  摘要：

  开发了一种新一代螺环分子 - 氧杂螺环 - 的一般实用方法。

  DOI：

  10.1039/d1sc03615g
• 作为产物：
  描述：

  1-Boc-3-氮杂环丁酮 、 3-Butenylmagnesium bromide 以 四氢呋喃 为溶剂， 以57 %的产率得到tert-butyl 3-(but-3-en-1-yl)-3-hydroxyazetidine-1-carboxylate
  参考文献：
  名称：

  催化对映选择性分子内 Oxa-Michael 反应生成 α,β-不饱和酯和酰胺

  摘要：

  描述了双功能亚氨基正膦 (BIMP) 催化的醇与束缚的低亲电性 Michael 受体的对映选择性分子内 oxa-Michael 反应。与之前的报告相比，反应性有所提高（1 天与 7 天相比）、优异的产率（高达 99%）和对映体比率（高达 99.5:0.5 er）。由于催化剂的模块化和可调性，反应范围广泛，包括取代的四氢呋喃 (THF) 和四氢吡喃 (THP)、氧杂螺环、糖和天然产物衍生物、二氢-(异)-苯并呋喃和异苯并二氢吡喃。最先进的计算研究表明，对映选择性源于 BIMP 催化剂和基材之间存在的几个有利的分子间氢键，从而诱导稳定的静电和轨道相互作用。

  DOI：

  10.1021/jacs.3c03182

文献信息

• Synthesis of a Family of Spirocyclic Scaffolds: Building Blocks for the Exploration of Chemical Space
  作者：Sarvesh Kumar、Paul D. Thornton、Thomas O. Painter、Prashi Jain、Jared Downard、Justin T. Douglas、Conrad Santini

  DOI：10.1021/jo400738b

  日期：2013.7.5

  This report describes the preparation Of a series of 17 novel racemic spirocyclic scaffolds that are intended for the creation of compound libraries by parallel synthesis for biological screening. Each scaffold features two points of orthogonal diversification. The scaffolds are related to each other in four ways: (1) through stepwise changes in the size of the nitrogen-bearing ring; (2) through the oxidation state of the carbon-centered point of diversification; (3) through the relative stereochemical orientation of the two diversification sites in those members that are stereogenic; and (4) through the provision of both saturated and unsaturated versions of the furan ring in the scaffold series derived from 3-piperidone. The scaffolds provide incremental changes in the relative Orientation of the diversity components that would be introduced onto them. The scaffolds feature high sp(3) carbon content which is essential for the three-dimensional exploration Of chemical space. This characteristic is particularly evident in those members of this family that bear two stereocenters, i.e., the two series derived from 3-piperidone and 3-pyrrolidinone. In the series derived from 3-piperidone we were able to "split the difference" between the two diastereomers by preparation of their corresponding unsaturated version.
• Oxa-spirocycles: synthesis, properties and applications
  作者：Kateryna Fominova、Taras Diachuk、Dmitry Granat、Taras Savchuk、Vladyslav Vilchynskyi、Oleksiy Svitlychnyi、Vladyslav Meliantsev、Igor Kovalchuk、Eduard Litskan、Vadym V. Levterov、Valentyn R. Badlo、Ruslan I. Vaskevych、Alla I. Vaskevych、Andrii V. Bolbut、Volodymyr V. Semeno、Rustam Iminov、Kostiantyn Shvydenko、Anastasiia S. Kuznetsova、Yurii V. Dmytriv、Daniil Vysochyn、Vasyl Ripenko、Andrei A. Tolmachev、Olexandra Pavlova、Halyna Kuznietsova、Iryna Pishel、Petro Borysko、Pavel K. Mykhailiuk

  DOI：10.1039/d1sc03615g

  日期：——

  A general practical approach to a new generation of spirocyclic molecules – oxa-spirocycles – is developed.

  开发了一种新一代螺环分子 - 氧杂螺环 - 的一般实用方法。
• Catalytic Enantioselective Intramolecular Oxa-Michael Reaction to α,β-Unsaturated Esters and Amides
  作者：Guanglong Su、Michele Formica、Ken Yamazaki、Trevor A. Hamlin、Darren J. Dixon

  DOI：10.1021/jacs.3c03182

  日期：2023.6.14

  bifunctional iminophosphorane (BIMP)-catalyzed, enantioselective intramolecular oxa-Michael reaction of alcohols to tethered, low electrophilicity Michael acceptors is described. Improved reactivity over previous reports (1 day vs 7 days), excellent yields (up to 99%), and enantiomeric ratios (up to 99.5:0.5 er) are demonstrated. The broad reaction scope, enabled by catalyst modularity and tunability, includes

  描述了双功能亚氨基正膦 (BIMP) 催化的醇与束缚的低亲电性 Michael 受体的对映选择性分子内 oxa-Michael 反应。与之前的报告相比，反应性有所提高（1 天与 7 天相比）、优异的产率（高达 99%）和对映体比率（高达 99.5:0.5 er）。由于催化剂的模块化和可调性，反应范围广泛，包括取代的四氢呋喃 (THF) 和四氢吡喃 (THP)、氧杂螺环、糖和天然产物衍生物、二氢-(异)-苯并呋喃和异苯并二氢吡喃。最先进的计算研究表明，对映选择性源于 BIMP 催化剂和基材之间存在的几个有利的分子间氢键，从而诱导稳定的静电和轨道相互作用。