(-)-(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-ethanesulfonyl chloride | 479678-73-4

• 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,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-ethanesulfonyl chloride
• 英文别名: 2-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]ethanesulfonyl chloride
• CAS: 479678-73-4
• 化学式: C₁₁H₁₇ClO₃S
• 分子量: 264.773
• InChiKey: LODQJRTUGRRUTI-LDYMZIIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  51.21
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (-)-(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-ethanesulfonyl chloride 在 ammonium hydroxide 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 20.0h， 生成 (-)-(4aS)-3,4,5,6,7,8-hexahydro-9,9-dimethyl-4a,7-methano-4aH-2,1-benzothiazine 2,2-dioxide
  参考文献：
  名称：

  Synthesis of a Six-Membered-Ring (2R)-10a-Homobornane-10a,2-sultam and Structural Comparison with Oppolzer's, Lang's, and King's Sultams

  摘要：

  The new six-membered-ring (2R)-10a-homobornane-10a,2-sultam (-)-3a was synthesized and its X-ray structural analysis was compared with that of the novel structure of the five-membered-ring (2R)-bornane-10,2-sultam analogues (-)-1a,b as well as with that already published for the six-membered-ring trans-decalin-like sultam 4a. Based on DN** density-function calculations and X-ray crystallographic studies of the N-methylated analogues (-)-1e and 4b and by comparing with the conformation of the N-fluoro derivatives (-)-1c and (+)-1d, the anomeric stabilization was estimated to be smaller than the 2.0-2.5 kcal/mol earlier suggested. The direction of pyramidalization is rationalized in terms of H-bond and steric and electronic interactions and extended to the known toluenesultam derivatives 10a-c.

  DOI：

  10.1002/1522-2675(200207)85:7<1973::aid-hlca1973>3.0.co;2-n
• 作为产物：
  描述：

  (+)-(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-ethanesulfonic acid 在 氯化亚砜 作用下， 反应 4.5h， 以63%的产率得到(-)-(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-ethanesulfonyl chloride
  参考文献：
  名称：

  Synthesis of a Six-Membered-Ring (2R)-10a-Homobornane-10a,2-sultam and Structural Comparison with Oppolzer's, Lang's, and King's Sultams

  摘要：

  The new six-membered-ring (2R)-10a-homobornane-10a,2-sultam (-)-3a was synthesized and its X-ray structural analysis was compared with that of the novel structure of the five-membered-ring (2R)-bornane-10,2-sultam analogues (-)-1a,b as well as with that already published for the six-membered-ring trans-decalin-like sultam 4a. Based on DN** density-function calculations and X-ray crystallographic studies of the N-methylated analogues (-)-1e and 4b and by comparing with the conformation of the N-fluoro derivatives (-)-1c and (+)-1d, the anomeric stabilization was estimated to be smaller than the 2.0-2.5 kcal/mol earlier suggested. The direction of pyramidalization is rationalized in terms of H-bond and steric and electronic interactions and extended to the known toluenesultam derivatives 10a-c.

  DOI：

  10.1002/1522-2675(200207)85:7<1973::aid-hlca1973>3.0.co;2-n