(R)-2-oxo-2-phenyl-benzo[c][1,2]thiazin-8-ol | 888712-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: (R)-2-oxo-2-phenyl-benzo[c][1,2]thiazin-8-ol
• 英文别名: (R)-8-(hydroxy)-2-S-oxa-2-S-phenyl-2,1-benzothiazine；R-2-Oxo-2-phenyl-benzo[c][1,2]thiazin-8-ol；(3R)-3-oxo-3-phenyl-3λ6-thia-2-azabicyclo[4.4.0]deca-1(6),2,4,7,9-pentaen-10-ol
• CAS: 888712-65-0
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: AJIZUFYRPAFLTC-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-oxo-2-phenyl-benzo[c][1,2]thiazin-8-ol 、 二苯基次膦酰氯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以91%的产率得到(R)-8-(P-oxa-diphenyl)-2-S-oxa-2-S-phenyl-2,1-benzothiazine
  参考文献：
  名称：

  New Chiral Benzothiazine Ligand and Its Use in the Synthesis of a Chiral Receptor

  摘要：

  The development of chiral ligands to direct the course and stereoselectivity of many catalytic asymmetric reactions is an important area of interest for many research groups. As part of a program examining the chemistry of 2,1-benzothiazines, we have prepared a new chiral benzothiazine ligand. This ligand can be made in as few as three steps from commercially available starting materials. Presented herein is the synthesis of the ligand along with the synthesis of a chiral molecular receptor that potentially presages a new class of chiral molecular tweezers.

  DOI：

  10.1021/jo060175c
• 作为产物：
  描述：

  (2-bromo-3-(methoxymethoxy)phenyl)methanol 在 palladium diacetate 盐酸 、 草酰氯 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 、 甲苯 为溶剂， 反应 53.0h， 生成 (R)-2-oxo-2-phenyl-benzo[c][1,2]thiazin-8-ol
  参考文献：
  名称：

  New Chiral Benzothiazine Ligand and Its Use in the Synthesis of a Chiral Receptor

  摘要：

  The development of chiral ligands to direct the course and stereoselectivity of many catalytic asymmetric reactions is an important area of interest for many research groups. As part of a program examining the chemistry of 2,1-benzothiazines, we have prepared a new chiral benzothiazine ligand. This ligand can be made in as few as three steps from commercially available starting materials. Presented herein is the synthesis of the ligand along with the synthesis of a chiral molecular receptor that potentially presages a new class of chiral molecular tweezers.

  DOI：

  10.1021/jo060175c

文献信息

• Giving a Second Chance to Ir/Sulfoximine-Based Catalysts for the Asymmetric Hydrogenation of Olefins Containing Poorly Coordinative Groups
  作者：Maria Biosca、Oscar Pàmies、Montserrat Diéguez

  DOI：10.1021/acs.joc.9b00829

  日期：2019.6.21

  This work identifies a family of Ir/phosphite-sulfoximine catalysts that has been successfully used in the asymmetric hydrogenation of olefins with poorly coordinative or noncoordinative groups. In comparison with analogue Ir/phosphine-sulfoximine catalysts previously reported, the presence of a phosphite group extended the range of olefins than can be efficiently hydrogenated. High enantioselectivities

  这项工作确定了Ir /亚磷酸酯-亚砜亚胺催化剂系列，已成功用于配位或非配位基团较弱的烯烃的不对称加氢中。与先前报道的类似的Ir /膦-亚砜亚胺催化剂相比，亚磷酸酯基团的存在扩展了烯烃的范围，而无法有效地氢化。对于包含相关的弱配位基团的各种烯烃（例如α，β-不饱和烯酮，酯，内酯和内酰胺以及烯基硼酸酯），已经实现了与对等最佳化合物相当的高对映选择性。
• New Chiral Benzothiazine Ligand and Its Use in the Synthesis of a Chiral Receptor
  作者：Michael Harmata、Nathan L. Calkins、Russell G. Baughman、Charles L. Barnes

  DOI：10.1021/jo060175c

  日期：2006.4.1

  The development of chiral ligands to direct the course and stereoselectivity of many catalytic asymmetric reactions is an important area of interest for many research groups. As part of a program examining the chemistry of 2,1-benzothiazines, we have prepared a new chiral benzothiazine ligand. This ligand can be made in as few as three steps from commercially available starting materials. Presented herein is the synthesis of the ligand along with the synthesis of a chiral molecular receptor that potentially presages a new class of chiral molecular tweezers.