(-)-[2R,S(R)]-N-[(E)-3-(methoxycarbonyl)prop-2-enoyl]bornane-10,2-sulfinamide | 345896-11-9

• 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: (-)-[2R,S(R)]-N-[(E)-3-(methoxycarbonyl)prop-2-enoyl]bornane-10,2-sulfinamide
• 英文别名: methyl (E)-4-[(1S,3R,5R,7R)-10,10-dimethyl-3-oxo-3λ4-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-4-oxobut-2-enoate
• CAS: 345896-11-9
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: RHKGSXDXWAZDNN-PJXMQRJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 (-)-[2R,S(R)]-N-[(E)-3-(methoxycarbonyl)prop-2-enoyl]bornane-10,2-sulfinamide 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (1R,2R,3R,4S)-3-{[(2R,3aS,6R,7aR)-hexahydro-8,8-dimethyl-2-oxido-3H-3a,6-methano-2,1-benzisothiazol-1-yl]carbonyl}bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 、 (1S,2R,3R,4R)-3-{[(2R,3aS,6R,7aR)-hexahydro-8,8-dimethyl-2-oxido-3H-3a,6-methano-2,1-benzisothiazol-1-yl]carbonyl}bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 、 (1R,2S,3S,4S)-3-{[(2R,3aS,6R,7aR)-hexahydro-8,8-dimethyl-2-oxido-3H-3a,6-methano-2,1-benzisothiazol-1-yl]carbonyl}bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 、 (1S,2S,3S,4R)-3-{[(2R,3aS,6R,7aR)-hexahydro-8,8-dimethyl-2-oxido-3H-3a,6-methano-2,1-benzisothiazol-1-yl]carbonyl}bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Stereoselectivity in the Cycloaddition of Cyclopentadiene toN-Fumaroyl-[2R,S(R)]-Bornane-10,2-sulfinamide Monomethyl Ester

  摘要：

  The cyclic [2R,S(R)]-bornane- 10,2-sulfinamide (-)-2b, an analogue of Oppolzer's camphor-derived sultam (-)-2a, was synthesized by reduction of the known N-alkylidenesulfinamide (+)-1b with NaBH4. The uncatalyzed [4 + 2] cycloaddition of cyclopentadiene to the methyl ester (-)-3b of the N-fumaroylsulfinamide, obtained from (-)-2b, proceeds with lower endo and pi -facial selectivity as compared to dienophiles (-)-3a,c. In contrast to these latter, the diastereoselectivity is reversed either in apolar CCl4, or in the presence of TiCl4,. This inversion is explained by a competitive C(alpha)-si addition on the reactive anti-s-trans conformer.

  DOI：

  10.1002/1522-2675(20010321)84:3<579::aid-hlca579>3.0.co;2-y
• 作为产物：
  描述：

  (1S,7R,R_S)-10,10-dimethyl-3-thia-4-azatricyclo[5.2.1.0^1,5]dec-4-ene 3-oxide 在 sodium tetrahydroborate 、 三甲基铝 作用下， 以 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 20.67h， 生成 (-)-[2R,S(R)]-N-[(E)-3-(methoxycarbonyl)prop-2-enoyl]bornane-10,2-sulfinamide
  参考文献：
  名称：

  Stereoselectivity in the Cycloaddition of Cyclopentadiene toN-Fumaroyl-[2R,S(R)]-Bornane-10,2-sulfinamide Monomethyl Ester

  摘要：

  The cyclic [2R,S(R)]-bornane- 10,2-sulfinamide (-)-2b, an analogue of Oppolzer's camphor-derived sultam (-)-2a, was synthesized by reduction of the known N-alkylidenesulfinamide (+)-1b with NaBH4. The uncatalyzed [4 + 2] cycloaddition of cyclopentadiene to the methyl ester (-)-3b of the N-fumaroylsulfinamide, obtained from (-)-2b, proceeds with lower endo and pi -facial selectivity as compared to dienophiles (-)-3a,c. In contrast to these latter, the diastereoselectivity is reversed either in apolar CCl4, or in the presence of TiCl4,. This inversion is explained by a competitive C(alpha)-si addition on the reactive anti-s-trans conformer.

  DOI：

  10.1002/1522-2675(20010321)84:3<579::aid-hlca579>3.0.co;2-y