(SS)-4-{1-[(1S-exo)-2-bornylsulfinyl]vinyl}-1,2-dihydro-7-methoxynaphthalene | 406463-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (SS)-4-{1-[(1S-exo)-2-bornylsulfinyl]vinyl}-1,2-dihydro-7-methoxynaphthalene
• 英文别名: (S_S)-4-{1-[(1S-exo)-2-bornylsulfinyl]vinyl}-1,2-dihydro-7-methoxynaphthalene
• CAS: 406463-85-2
• 化学式: C₂₃H₃₀O₂S
• 分子量: 370.556
• InChiKey: YZPMPDGKXYPJLP-KPGKHOEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (SS)-4-{1-[(1S-exo)-2-bornylsulfinyl]vinyl}-1,2-dihydro-7-methoxynaphthalene 在 间氯过氧苯甲酸 作用下， 生成 4-{1-[(1S-exo)-2-bornylsulfonyl]vinyl}-1,2-dihydro-7-methoxynaphthalene
  参考文献：
  名称：

  Enantiopure 2-sulfinylbuta-1,3-dienes in Diels–Alder cycloadditions: a stereoselective approach to an azasteroidal skeleton

  摘要：

  The synthesis of enantiopure 4-[1-(alkylsulfinyl)vinyl]-1,2-dihydronaphthalenes and their Diels-Alder reactions are described. Cycloadditions with N-phenylmaleimide occur under thermal conditions, very slowly but with notable stereoselection, giving in each case just one of the two endo adducts in high yield. The obtained 16-azasteroid derivatives undergo chiral auxiliary removal in the presence of TMSI. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00507-9
• 作为产物：
  描述：

  1,2-dihydro-4-ethynyl-7-methoxynaphthalene 、 (1S-exo)-2-bornyl 2-cyanoethylsulfoxide 以 xylene 为溶剂， 反应 1.5h， 以43%的产率得到(SS)-4-{1-[(1S-exo)-2-bornylsulfinyl]vinyl}-1,2-dihydro-7-methoxynaphthalene
  参考文献：
  名称：

  Enantiopure 2-sulfinylbuta-1,3-dienes in Diels–Alder cycloadditions: a stereoselective approach to an azasteroidal skeleton

  摘要：

  The synthesis of enantiopure 4-[1-(alkylsulfinyl)vinyl]-1,2-dihydronaphthalenes and their Diels-Alder reactions are described. Cycloadditions with N-phenylmaleimide occur under thermal conditions, very slowly but with notable stereoselection, giving in each case just one of the two endo adducts in high yield. The obtained 16-azasteroid derivatives undergo chiral auxiliary removal in the presence of TMSI. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00507-9