(2R,3R)-3-<<(3aS,6R,7aR)-1,4,5,6,7,7a-hexahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano<2,1>benzisothiazol-1-yl>carbonyl>bicyclo<2.2.1>hept-5-ene-2-carboxylic acid benzyl ester | 221663-97-4

• 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: (2R,3R)-3-<<(3aS,6R,7aR)-1,4,5,6,7,7a-hexahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano<2,1>benzisothiazol-1-yl>carbonyl>bicyclo<2.2.1>hept-5-ene-2-carboxylic acid benzyl ester
• 英文别名: benzyl (1R,2R,3R,4S)-3-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]bicyclo[2.2.1]hept-5-ene-2-carboxylate；benzyl (1R,2R,3R,4S)-3-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]bicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 221663-97-4
• 化学式: C₂₆H₃₁NO₅S
• 分子量: 469.602
• InChiKey: QPXYYQRHUGNGRB-CVWCGVDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-<<(3aS,6R,7aR)-1,4,5,6,7,7a-hexahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano<2,1>benzisothiazol-1-yl>carbonyl>bicyclo<2.2.1>hept-5-ene-2-carboxylic acid benzyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (-)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene
  参考文献：
  名称：

  Stereoselectivity in the TiCl4-Catalyzed [4+2] Cycloaddition of Cyclopentadiene to (2R)-Bornane-10,2-sultam Derivatives of Fumaric Acid Monoesters

  摘要：

  The [4 + 2] cycloaddition of cyclopentadiene to the (2R)-bornane-10,2-sultam derivative (-)-1b of fumaric monomethyl ester proceeds with high endo and pi-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl4. The major diastereoisomer endo-(2R,3R)-2b, isolated in 87% yield by crystallization, was subjected to X-ray crystal-structure analysis. Steric influence of ethyl- and benzyl-ester analogues (-)-1c and (-)-1d, respectively, is also reported.

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<182::aid-hlca182>3.0.co;2-p
• 作为产物：
  描述：

  环戊二烯 、 (-)-(2R)-N-<(E)-3-<(benzyloxy)carbonyl>prop-2-enoyl>bornane-10,2-sultam 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以73%的产率得到(2R,3R)-3-<<(3aS,6R,7aR)-1,4,5,6,7,7a-hexahydro-8,8-dimethyl-2,2-dioxido-3H-3a,6-methano<2,1>benzisothiazol-1-yl>carbonyl>bicyclo<2.2.1>hept-5-ene-2-carboxylic acid benzyl ester
  参考文献：
  名称：

  Stereoselectivity in the TiCl4-Catalyzed [4+2] Cycloaddition of Cyclopentadiene to (2R)-Bornane-10,2-sultam Derivatives of Fumaric Acid Monoesters

  摘要：

  The [4 + 2] cycloaddition of cyclopentadiene to the (2R)-bornane-10,2-sultam derivative (-)-1b of fumaric monomethyl ester proceeds with high endo and pi-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl4. The major diastereoisomer endo-(2R,3R)-2b, isolated in 87% yield by crystallization, was subjected to X-ray crystal-structure analysis. Steric influence of ethyl- and benzyl-ester analogues (-)-1c and (-)-1d, respectively, is also reported.

  DOI：

  10.1002/(sici)1522-2675(19990210)82:2<182::aid-hlca182>3.0.co;2-p

文献信息

• Stereoselectivity in the TiCl4-Catalyzed [4+2] Cycloaddition of Cyclopentadiene to (2R)-Bornane-10,2-sultam Derivatives of Fumaric Acid Monoesters
  作者：Michal Achmatowicz、Christian Chapuis、Piotr Rzepecki、Janusz Jurczak

  DOI：10.1002/(sici)1522-2675(19990210)82:2<182::aid-hlca182>3.0.co;2-p

  日期：1999.2.10

  The [4 + 2] cycloaddition of cyclopentadiene to the (2R)-bornane-10,2-sultam derivative (-)-1b of fumaric monomethyl ester proceeds with high endo and pi-facial diastereoselectivity in the presence of 0.5 mol-equiv. of TiCl4. The major diastereoisomer endo-(2R,3R)-2b, isolated in 87% yield by crystallization, was subjected to X-ray crystal-structure analysis. Steric influence of ethyl- and benzyl-ester analogues (-)-1c and (-)-1d, respectively, is also reported.