(2R,3S,6R)-2-溴-8-氯-1,1,9-三甲基-5-亚甲基-螺[5.5]十一碳-8-烯-3-醇 | 55303-97-4

• 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
• 中文名称: (2R,3S,6R)-2-溴-8-氯-1,1,9-三甲基-5-亚甲基-螺[5.5]十一碳-8-烯-3-醇
• 英文名称: Elatol
• 英文别名: (3S,4R,6R)-4-bromo-10-chloro-5,5,9-trimethyl-1-methylidenespiro[5.5]undec-9-en-3-ol
• CAS: 55303-97-4
• 化学式: C₁₅H₂₂BrClO
• 分子量: 333.696
• InChiKey: HZKGRCIKQBHSNA-KCQAQPDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2906199090

反应信息

• 作为反应物：
  描述：

  (2R,3S,6R)-2-溴-8-氯-1,1,9-三甲基-5-亚甲基-螺[5.5]十一碳-8-烯-3-醇 在 acid silica gel 、 间氯过氧苯甲酸 作用下， 生成 (1R,3R,4S)-3-Bromo-4-hydroxy-2,2,8-trimethyl-tricyclo[6.2.2.01,6]dodec-6-en-9-one
  参考文献：
  名称：

  Biomimetic approach to the synthesis of rhodolaureol and rhodolauradiol

  摘要：

  DOI：

  10.1016/s0040-4039(00)87351-7
• 作为产物：
  描述：

  9-hydroxy-β-iso-obtusene 在 lithium perchlorate 、 溶剂黄146 作用下， 以 正庚烷 为溶剂， 以100%的产率得到(2R,3S,6R)-2-溴-8-氯-1,1,9-三甲基-5-亚甲基-螺[5.5]十一碳-8-烯-3-醇
  参考文献：
  名称：

  Biomimetic approach to the synthesis of rhodolaureol and rhodolauradiol

  摘要：

  DOI：

  10.1016/s0040-4039(00)87351-7

文献信息

• Cytotoxic Activity of Semi-Synthetic Derivatives of Elatol and Isoobtusol
  作者：Karen L. Lang、Izabella T. Silva、Lara A. Zimmermann、Cíntia Lhullier、Maria V. Mañalich Arana、Jorge A. Palermo、Miriam Falkenberg、Cláudia M. O. Simões、Eloir P. Schenkel、Fernando J. Durán

  DOI：10.3390/md10102254

  日期：——

  In the present study, the in vitro cytotoxic effects of six semi-synthetic derivatives of elatol (1) and isoobtusol (2) were investigated. Chemical modifications were performed on the hydroxyl groups aiming to get derivatives of different polarity, namely the hemisuccinate, carbamate and sulfamate. The structural elucidation of the new derivatives was based on detailed NMR and MS spectroscopic analyses. The in vitro cytotoxicity of compounds 1 to 8 was evaluated against A459 and RD tumor cell lines with CC50 values ranging from 4.93 to 41.53 µM. These results suggest that the structural modifications performed on both compounds could be considered a good strategy to obtain more active derivatives.

  本研究调查了艾拉朵醇（1）和异艾拉朵醇（2）的六种半合成衍生物的体外细胞毒性作用。对羟基进行了化学修饰，以获得不同极性的衍生物，即半琥珀酸酯、氨基甲酸酯和氨基磺酸酯。新衍生物的结构阐明基于详细的核磁共振和质谱分析。评估了化合物 1 至 8 对 A459 和 RD 肿瘤细胞系的体外细胞毒性，其 CC50 值为 4.93 至 41.53 µM。这些结果表明，对这两种化合物进行结构改造是获得更多活性衍生物的良好策略。
• Chamigrane metabolites from a Jamaican variety of laurencia obtusa
  作者：Mary R. Brennan、Karen L. Erickson、Donna A. Minott、Keith O. Pascoe

  DOI：10.1016/s0031-9422(00)82349-3

  日期：1987.1

  Abstract Two new sesquiterpenoid metabolites have been characterized from a Jamaican variety of the marine alga Laurencia obtusa. These are 2-chloro-3-hydroxy-α-chamigren-9-one, with an unusual cis-relationship of the heteroatoms at the 2,3-positions, and its intramolecular conjugate addition derivative possessing a cineole moiety fused to a cyclohexane ring.

  摘要 已从牙买加海藻 Laurencia obtusa 的变种中表征了两种新的倍半萜类代谢物。它们是 2-chloro-3-hydroxy-α-chamigren-9-one，在 2,3-位上具有不寻常的杂原子顺式关系，其分子内共轭加成衍生物具有与环己烷环稠合的桉树脑部分.
• The Catalytic Asymmetric Total Synthesis of Elatol
  作者：David E. White、Ian C. Stewart、Robert H. Grubbs、Brian M. Stoltz

  DOI：10.1021/ja710294k

  日期：2008.1.1

  Described in this report is the first total synthesis of elatol, a halogenated sesquiterpene in the chamigrene natural product family. The key disconnections in our synthetic approach include an enantioselective decarboxylative allylation to form the all-carbon quaternary stereocenter and a ring-closing olefin metathesis to concomitantly form the spirocyclic core as well as the fully substituted chlorinated olefin. This strategy represents a general platform for accessing the chamigrene natural product family, as demonstrated by the synthesis of (+)-laurencenone B as an intermediate in our route.
• A general enantioselective route to the chamigrene natural product family
  作者：David E. White、Ian C. Stewart、Brinton A. Seashore-Ludlow、Robert H. Grubbs、Brian M. Stoltz

  DOI：10.1016/j.tet.2010.04.128

  日期：2010.6

  Described in this report is an enantioselective route toward the chamigrene natural product family. The key disconnections in our synthetic approach include sequential enantioselective decarboxylative allylation and ring-closing olefin metathesis to form the all-carbon quaternary stereocenter and spirocyclic core present in all members of this class of compounds. The generality of this strategy is demonstrated by the first total syntheses of elatol and the proposed structure of laurencenone B, as well as the first enantioselective total syntheses of laurencenone C and alpha-chamigrene. A brief exploration of the substrate scope of the enantioselective decarboxylative allylation/ring-closing metathesis sequence with fully substituted vinyl chlorides is also presented. (C) 2010 Elsevier Ltd. All rights reserved.
• CAPON, ROBERT J.;GHISALBERTI, EMILIO L.;MORI, TREVOR A.;JEFFERIES, PHILLI+, J. NATUR. PROD., 51,(1988) N, C. 1302-1304
  作者：CAPON, ROBERT J.、GHISALBERTI, EMILIO L.、MORI, TREVOR A.、JEFFERIES, PHILLI+

  DOI：——

  日期：——