(R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]-selenepin | 297163-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]-selenepin
• 英文别名: 13-selenapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene
• CAS: 297163-60-1
• 化学式: C₂₂H₁₆Se
• 分子量: 359.329
• InChiKey: AMOOLRRQEHMXRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]-selenepin 在 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以95%的产率得到(R)-3,5-dihydrodinaphtho[2,1-c:1',2'-e]selenepin 4-oxide
  参考文献：
  名称：

  Synthesis of (R)-4,5-Dihydro-3H-Dinaphtho-[2,1-c:1',2'-e]Selenepin Oxide and Preliminary Studies on Its Use in the Oxidation of Sulfides

  摘要：

  The first synthesis (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]-selenepin oxide 1 has been achieved from (R)-(+)-1,1'-bi-2-naphthol, which in turn was obtained by resolution of rac-1,1'-bi-2-naphthol. Palladium catalyzed alkoxy-carbonylation of ditriflate 4 gave dimethyl eater 5 which was then reduced and the resultant diol converted to key intermediate chloride 8. Cyclization with sodium selenolate gave novel enantiomerically pure selenide 9, which upon oxidation yielded the desired selenoxide (R)-1. Preliminary studies on the oxidation of sulfides to sulfoxides using 1 and 2,2,2-trifluoroethane sulfonic acid are also described.

  DOI：

  10.1080/00397910008087448
• 作为产物：
  描述：

  (+/-)-2,2'-bis(hydroxymethyl)-1,1'-binaphthyl 在 selenium 、 sodium tetrahydroborate 、 N-氯代丁二酰亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.5h， 生成 (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]-selenepin
  参考文献：
  名称：

  Synthesis of (R)-4,5-Dihydro-3H-Dinaphtho-[2,1-c:1',2'-e]Selenepin Oxide and Preliminary Studies on Its Use in the Oxidation of Sulfides

  摘要：

  The first synthesis (R)-4,5-dihydro-3H-dinaphtho-[2,1-c:1',2'-e]-selenepin oxide 1 has been achieved from (R)-(+)-1,1'-bi-2-naphthol, which in turn was obtained by resolution of rac-1,1'-bi-2-naphthol. Palladium catalyzed alkoxy-carbonylation of ditriflate 4 gave dimethyl eater 5 which was then reduced and the resultant diol converted to key intermediate chloride 8. Cyclization with sodium selenolate gave novel enantiomerically pure selenide 9, which upon oxidation yielded the desired selenoxide (R)-1. Preliminary studies on the oxidation of sulfides to sulfoxides using 1 and 2,2,2-trifluoroethane sulfonic acid are also described.

  DOI：

  10.1080/00397910008087448

文献信息

• Kinetic Resolution of Racemic Ferrocenylphosphine Compounds by Enantioselective Oxidation Using Cyclic Selenoxides Having a Chiral Ligand
  作者：Yoshihiro Miyake、Akiyoshi Yamauchi、Yoshiaki Nishibayashi、Sakae Uemura

  DOI：10.1246/bcsj.76.381

  日期：2003.2

  selenoxides having an optically active binaphthyl skeleton work as the reagents for enantioselective oxidation of phosphines to the corresponding phosphine oxides. Treatment of a racemic 2-oxazolin-2-ylferrocenylphosphine with one of the selenoxides in carbon tetrachloride in the presence of phenol affords the corresponding phosphine oxide together with the unreacted starting phosphine, both with moderate

  具有旋光联萘骨架的环状硒氧化物用作将膦对映选择性氧化成相应氧化膦的试剂。在苯酚的存在下，用四氯化碳中的一种氧化硒处理外消旋 2-恶唑啉-2-基二茂铁基膦，得到相应的氧化膦和未反应的起始膦，两者都具有中等对映选择性（氧化膦，高达 13% ee ; 膦，高达 29% ee)。