l-isobornyl chloroformate | 34771-95-4

• 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: l-isobornyl chloroformate
• 英文别名: (-)-isobornyl chloroformate；[(1R,2R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] carbonochloridate
• CAS: 34771-95-4
• 化学式: C₁₁H₁₇ClO₂
• 分子量: 216.708
• InChiKey: SEMILPCRBUIZJO-XLDPMVHQSA-N

物化性质

• 沸点：
  240.1±7.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  l-isobornyl chloroformate 在 sodium hydroxide 、 碘 、 silver trifluoroacetate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 l-isobornyl (1,2,3,4-tetrahydro-8-methoxy-5-iodo-2-naphthalenyl)carbamate
  参考文献：
  名称：

  l-1,2,3,4-Tetrahydro-8-methoxy-5-(methylthio)-2-naphthalenamine: a potent and selective agonist at .alpha.1-adrenoceptors

  摘要：

  1,2,3,4-Tetrahydro-8-methoxy-5-(methylthio)-2-naphthalenamine (SK&F-89748) has been resolved into d and l enantiomers and characterized pharmacologically. The more active isomer is the l, which has the S configuration as established by single-crystal X-ray diffraction studies. This compound is a potent and selective alpha 1-agonist with an EC50 in the isolated perfused rabbit ear artery of 9 +/- 2 nM. In several preparations, it has shown an alpha 1/alpha 2 selectivity ratio of over 100 and will be a useful tool for characterizing receptor subtypes.

  DOI：

  10.1021/jm00363a002
• 作为产物：
  描述：

  光气 、 isoborneol 以 四氢呋喃 为溶剂， 反应 0.75h， 以80%的产率得到l-isobornyl chloroformate
  参考文献：
  名称：

  Harris, Joanna M.; Bolessa, Evon A.; Mendonca, Aubrey J., Journal of the Chemical Society. Perkin transactions I, 1995, # 15, p. 1945 - 1950

  摘要：

  DOI：

文献信息

• The preparation of the (6R)- and (6S)-diastereoisomers of 5-formyltetrahydrofolate (leucovorin)
  作者：Jonathan Owens、Lilias Rees、Colin J. Suckling、Hamish C. S. Wood

  DOI：10.1039/p19930000871

  日期：——

  The separation of the (6R)- and (6S)-diastereoisomers of tetrahydrofolic acid by derivatisation on N-5 with chiral auxiliary reagents followed by fractional crystallisation or extraction is described. Chloroformates of chiral alcohols were used as chiral auxiliaries and those derived from cyclic terpene alcohols were found to be most effective for the separation. The cleavage of the derivative and conversion

  描述了通过在N-5上用手性辅助试剂衍生化四氢叶酸的（6 R）-和（6 S）-非对映异构体，然后进行分步结晶或萃取的方法。手性醇的氯甲酸酯被用作手性助剂，而衍生自环状萜烯醇的氯甲酸酯对于分离是最有效的。衍生物的裂解和原位转化研究了将5,10-亚甲基四氢叶酸水解后得到5-甲酰基四氢叶酸（亚叶酸钙）的衍生化四氢叶酸；（-）-薄荷醇的化合物是唯一将令人满意的分离与足够的不稳定性结合起来以有效转化为5-甲酰基四氢叶酸的化合物。描述了产物的表征和光学纯度。
• Fujino,M. et al., Chemical and pharmaceutical bulletin, 1972, vol. 20, # 5, p. 1017 - 1020
  作者：Fujino,M. et al.

  DOI：——

  日期：——
• US4959472A
  申请人：——

  公开号：US4959472A

  公开（公告）日：1990-09-25
• Harris, Joanna M.; Bolessa, Evon A.; Mendonca, Aubrey J., Journal of the Chemical Society. Perkin transactions I, 1995, # 15, p. 1945 - 1950
  作者：Harris, Joanna M.、Bolessa, Evon A.、Mendonca, Aubrey J.、Feng, Sheng-Chu、Vederas, John C.

  DOI：——

  日期：——
• l-1,2,3,4-Tetrahydro-8-methoxy-5-(methylthio)-2-naphthalenamine: a potent and selective agonist at .alpha.1-adrenoceptors
  作者：Robert M. DeMarinis、J. Paul Hieble

  DOI：10.1021/jm00363a002

  日期：1983.9

  1,2,3,4-Tetrahydro-8-methoxy-5-(methylthio)-2-naphthalenamine (SK&F-89748) has been resolved into d and l enantiomers and characterized pharmacologically. The more active isomer is the l, which has the S configuration as established by single-crystal X-ray diffraction studies. This compound is a potent and selective alpha 1-agonist with an EC50 in the isolated perfused rabbit ear artery of 9 +/- 2 nM. In several preparations, it has shown an alpha 1/alpha 2 selectivity ratio of over 100 and will be a useful tool for characterizing receptor subtypes.