(1S,5R,7R)-3-butyl-3-chloro-10,10-dimethyl-4-oxa-3lambda4-telluratricyclo[5.2.1.01,5]decane | 199294-21-8

• 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: (1S,5R,7R)-3-butyl-3-chloro-10,10-dimethyl-4-oxa-3lambda4-telluratricyclo[5.2.1.01,5]decane
• 英文别名: (1S,5R,7R)-3-butyl-3-chloro-10,10-dimethyl-4-oxa-3λ4-telluratricyclo[5.2.1.01,5]decane
• CAS: 199294-21-8
• 化学式: C₁₄H₂₅ClOTe
• 分子量: 372.405
• InChiKey: YNKZAGREFICMNC-YRGRVCCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1S,5R,7R)-3-butyl-3-chloro-10,10-dimethyl-4-oxa-3lambda4-telluratricyclo[5.2.1.01,5]decane 在 sodium bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 butyl-ethyl-[[(1S,2R,4R)-2-hydroxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]methyl]tellanium;chloride
  参考文献：
  名称：

  Diastereoselective Synthesis and Stereochemical Research of Optically Pure Telluronium Salts

  摘要：

  The synthesis of optically pure telluronium salts 4a-i, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, has been achieved in high yield and selectivity by the reaction of chiral alkoxytelluranes 3a-i with organolithium and Grignard reagents. Both diastereoisomers of ethyl(2-exo-hydroxy-10-bornyl)methyltelluronium chloride (4a,b) and butyl(2-exo-hydroxy-10-bornyl)methyltelluronium chloride (4c,d) have been synthesized in optically pure form in high yield and with excellent diastereoselectivity. The method has been used for the asymmetric synthesis of chiral benzyl- and allyltelluronium salts 5a-h. Structures of these salts have been confirmed by X-ray analyses of 4a and 4b, which indicated that all of the salts have their pyramidal geometrical structures around the tellurium atom. The thermal and optical stability and the possible mechanisms of the reaction are also discussed.

  DOI：

  10.1021/jo9803131
• 作为产物：
  描述：

  10-iodocamphor 在 sodium tetrahydroborate 、 次氯酸叔丁酯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.66h， 生成 (1S,5R,7R)-3-butyl-3-chloro-10,10-dimethyl-4-oxa-3lambda4-telluratricyclo[5.2.1.01,5]decane
  参考文献：
  名称：

  Diastereoselective Synthesis and Stereochemical Research of Optically Pure Telluronium Salts

  摘要：

  The synthesis of optically pure telluronium salts 4a-i, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, has been achieved in high yield and selectivity by the reaction of chiral alkoxytelluranes 3a-i with organolithium and Grignard reagents. Both diastereoisomers of ethyl(2-exo-hydroxy-10-bornyl)methyltelluronium chloride (4a,b) and butyl(2-exo-hydroxy-10-bornyl)methyltelluronium chloride (4c,d) have been synthesized in optically pure form in high yield and with excellent diastereoselectivity. The method has been used for the asymmetric synthesis of chiral benzyl- and allyltelluronium salts 5a-h. Structures of these salts have been confirmed by X-ray analyses of 4a and 4b, which indicated that all of the salts have their pyramidal geometrical structures around the tellurium atom. The thermal and optical stability and the possible mechanisms of the reaction are also discussed.

  DOI：

  10.1021/jo9803131

文献信息

• First stereoselective synthesis of enantiomerically pure telluronium salts by the reaction of chiral halooxatelluranes with Grignard reagents
  作者：Jian Zhang、Shinichi Saito、Toru Koizumi

  DOI：10.1016/s0957-4166(97)00459-x

  日期：1997.10

  We prepared a series of enantiomerically pure benzyl and allyl telluronium salts 2 and 4, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, in high yield and selectivity by the reaction of chiral haloalkoxytelluranes 1 and 3 with Grignard reagents. A sharp pyramidal structure with S absolute configuration at the tellurium atom was confirmed by an X-ray analysis of 2c. (C) 1997 Published by Elsevier Science Ltd.
• Diastereoselective Synthesis and Stereochemical Research of Optically Pure Telluronium Salts
  作者：Jian Zhang、Shinichi Saito、Toru Koizumi

  DOI：10.1021/jo9803131

  日期：1998.8.1

  The synthesis of optically pure telluronium salts 4a-i, using the 2-exo-hydroxy-10-bornyl group as a chiral ligand, has been achieved in high yield and selectivity by the reaction of chiral alkoxytelluranes 3a-i with organolithium and Grignard reagents. Both diastereoisomers of ethyl(2-exo-hydroxy-10-bornyl)methyltelluronium chloride (4a,b) and butyl(2-exo-hydroxy-10-bornyl)methyltelluronium chloride (4c,d) have been synthesized in optically pure form in high yield and with excellent diastereoselectivity. The method has been used for the asymmetric synthesis of chiral benzyl- and allyltelluronium salts 5a-h. Structures of these salts have been confirmed by X-ray analyses of 4a and 4b, which indicated that all of the salts have their pyramidal geometrical structures around the tellurium atom. The thermal and optical stability and the possible mechanisms of the reaction are also discussed.