3-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylselanyl)-propionic acid ethyl ester | 218623-59-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylselanyl)-propionic acid ethyl ester
• CAS: 218623-59-7
• 化学式: C₁₅H₂₆O₃Se
• 分子量: 333.33
• InChiKey: CNFDHFHMEAPLSJ-LALPHHSUSA-N

物化性质

• 沸点：
  400.576±20.00 °C(Press: 760.00 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylselanyl)-propionic acid ethyl ester 在 sodium hydroxide 、 次氯酸叔丁酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 spiro[4H-3α,6-methano-3H-1,2-bezoxasulfole-2,2'λ⁴-3',4'-dihydro-[5H-1,2]oxaselenol]-5'-one,5,6,7,7a-tetrahydro-8,8-dimethyl-(2R-(2α,3aα,6α,7aβ))
  参考文献：
  名称：

  First synthesis and stereochemistry of enantiomerically pure spiroselenurane and spirotellurane using the 2-exo-hydroxy-10-bornyl group as a chiral ligand

  摘要：

  The first synthesis of enantiomerically pure spiroselenuranes 8a-d and spirotelluranes 12a,b, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, has been developed and proceeds in good yield and with excellent diastereoselectivity. The X-ray analysis of spirotellurane 12a indicated that the spirochalcogenuranes have a trigonal bipyramidal (TBP) structure around the chalcogenium atom. A comparison of the spectroscopic properties of spirochalcogenuranes is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00352-8
• 作为产物：
  描述：

  3-溴丙酸乙酯 、 di-(2-exo-hydroxy-10-bornyl) diselenide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以100%的产率得到3-((1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethylselanyl)-propionic acid ethyl ester
  参考文献：
  名称：

  First synthesis and stereochemistry of enantiomerically pure spiroselenurane and spirotellurane using the 2-exo-hydroxy-10-bornyl group as a chiral ligand

  摘要：

  The first synthesis of enantiomerically pure spiroselenuranes 8a-d and spirotelluranes 12a,b, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, has been developed and proceeds in good yield and with excellent diastereoselectivity. The X-ray analysis of spirotellurane 12a indicated that the spirochalcogenuranes have a trigonal bipyramidal (TBP) structure around the chalcogenium atom. A comparison of the spectroscopic properties of spirochalcogenuranes is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00352-8