4,4-dimethyl-6-propyltetrahydro-1,2,3-oxathiazine-2,2-dioxide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫酸及其衍生物
• 英文名称: 4,4-dimethyl-6-propyltetrahydro-1,2,3-oxathiazine-2,2-dioxide
• 英文别名: 4,4-Dimethyl-6-propyloxathiazinane 2,2-dioxide
• 化学式: C₈H₁₇NO₃S
• 分子量: 207.294
• InChiKey: UKTPXJSULZIFSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基-4-庚醇 在 dirhodium tetraacetate 碘苯二乙酸 、 magnesium oxide 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4,4-dimethyl-6-propyltetrahydro-1,2,3-oxathiazine-2,2-dioxide
  参考文献：
  名称：

  通过选择性 C-H 键氧化合成 1,3-双官能胺衍生物

  摘要：

  DOI：

  10.1021/ja011033x

文献信息

• GENERAL CATALYST FOR C-H FUNCTIONALIZATION
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20160272662A1

  公开（公告）日：2016-09-22

  The invention provides novel manganese catalysts such as [Mn( t BuPc)], which are general for the amination of all types of C(sp 3 )-H bonds (aliphatic, allylic, propargylic, benzylic, ethereal), including strong 1 o aliphatic C—H bonds, while achieving excellent chemoselectivity, stereospecificity, and high functional group tolerance. We demonstrate the late-stage diversification of bioactive complex molecules that encompass the range of C(sp 3 )-H bond types, such as selective 1 o C—H aminations of betulinic acid and pleuromutilin derivatives. The catalysts' unprecedented balance of reactivity and selectivity is in part attributed to its mechanism of C—H amination that lies between stepwise and concerted.

  该发明提供了新型的锰催化剂，如[Mn(tBuPc)]，适用于所有类型的C(sp3)-H键（脂肪族、烯丙基、丙炔基、苄基、乙醚基）的胺化，包括强1°脂肪族C—H键，同时实现优异的化学选择性、立体特异性和高官能团耐受性。我们展示了包括选择性1°C—H键胺化在内的生物活性复合分子的晚期多样化，这些复合分子涵盖了各种C(sp3)-H键类型，如对苯二酚酸和普鲁莫铁霉素衍生物的选择性1°C—H键胺化。催化剂在反应性和选择性之间的前所未有的平衡部分归因于其C—H键胺化机制介于逐步和协同之间。
• Cooperative Effect of Two Metals: CoPd(OAc)₄-Catalyzed CH Amination and Aziridination
  作者：Guan-Hao Huang、Jian-Min Li、Jing-Jyun Huang、Jyun-Dai Lin、Gary Jing Chuang

  DOI：10.1002/chem.201304633

  日期：2014.4.25

  intramolecular CH amination and aziridination reactions were developed. Sulfamate esters were converted to oxathiazinanes by using CoPd(OAc)4 as catalyst and PhI(OAc)2 as oxidant. The mutual presence of both Co and Pd is crucial for the catalytic activity. This combination of two metals with simple acetate ligands provides an economical alternative to the Rh‐catalyzed insertion of nitrenoids into CH bonds

  首次开发了Co / Pd共催化的分子内CH氨基化和叠氮化反应。通过使用CoPd（OAc）4作为催化剂和PhI（OAc）2作为氧化剂，将氨基磺酸酯转化为恶二嗪。Co和Pd的共同存在对于催化活性至关重要。两种金属的简单乙酸配体这种组合提供了一种经济的替代nitrenoids的铑催化的插入成C  H键。
• A mechanistic analysis of the Rh-catalyzed intramolecular C–H amination reaction
  作者：Kristin Williams Fiori、Christine G. Espino、Benjamin H. Brodsky、J. Du Bois

  DOI：10.1016/j.tet.2008.11.073

  日期：2009.4

  A detailed mechanistic investigation of the intramolecular dirhodium tetracarboxylate-catalyzed sulfamate ester C-H amination reaction is presented. These studies provide support for the formation of a sulfamate-derived iminoiodinane, which reacts rapidly with the rhodium catalyst to generate a nitrenoid-type oxidant. Reactivity patterns, Hammett analysis, kinetic isotope measurement, and a cyclopropane clock experiment are indicative of a concerted, asynchronous transition structure in the product-determining C-H insertion event. (C) 2008 Published by Elsevier Ltd.
• US9770711B2
  申请人：——

  公开号：US9770711B2

  公开（公告）日：2017-09-26
• Synthesis of 1,3-Difunctionalized Amine Derivatives through Selective C−H Bond Oxidation
  作者：Christine G. Espino、Paul M. Wehn、Jessica Chow、J. Du Bois

  DOI：10.1021/ja011033x

  日期：2001.7.1