1-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethanol | 33829-99-1

• 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: 1-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethanol
• 英文别名: (6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol；1-(6,6-Dimethyl-2-bicyclo[3.1.1]hept-2-enyl)ethanol
• CAS: 33829-99-1
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: SBKWIMOJGZNSDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethanol 在 四氯化碳 、 copper(l) iodide 、 三苯基膦 作用下， 反应 17.0h， 生成 (1S)-2-异丙基-6,6-二甲基双环[3.1.1]庚-2-烯
  参考文献：
  名称：

  Hydroboration. 90. Synthesis of 2-Isobutyl- and 2-Isopropylapopinenes. Rates and Stoichiometry of the Hydroboration of 2-Organylapopinenes with Borane-Methyl Sulfide and Borane-Tetrahydrofuran

  摘要：

  Two higher analogues of Lu-pinene, 2-isobutyl- and 2-isopropylapopinenes, promising chiral auxiliaries for asymmetric hydroboration, were readily synthesized from alpha-pinene in good chemical yield. A quantitative study was made of the rates and stoichiometry of the hydroboration of a number of representative 2-organylapopinenes (2-R-apopinenes) with representative boranes, such as BH3.SMe(2) (BMS) and BH3.THF, in order to develop a convenient procedure for the synthesis of mono- and bis(2-organylapoisopinocampheyl)boranes [2-R-apoisopinylborane (RapBH(2)) and bis(2-R-apoisopinyl)borane (Rap(2)BH), respectively],under investigation as possible improved asymmetric hydroborating reagents. It was evident that the sterically bulkier 2-R-apopinenes such as 2-phenyl- and 2-isopropylapopinenes reacted with boranes at room temperature to form essentially RapBH(2) in greater than or equal to 195 % yield, while a yield of greater than or equal to 90 % was realized in the case of 2-isobutylapopinene; However, alpha-pinene, and 2-ethyl- and 2-n-propylapopinenes smoothly reacted with boranes to form a mixture of RapBH(2) and Rap(2)BH. Under the reaction conditions employed, 2-ethyl-, 2-n-propyl-, 2-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes failed to produce clean Rap(2)BH. The rate of hydroboration decreased significantly with increase in bulk of the organyl group at the 2-position of the apopinene.

  DOI：

  10.1021/jo00087a016
• 作为产物：
  描述：

  甲基氯化镁 、 桃金娘烯醛 以 四氢呋喃 为溶剂， 反应 12.0h， 以92%的产率得到1-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)-ethanol
  参考文献：
  名称：

  Hydroboration. 90. Synthesis of 2-Isobutyl- and 2-Isopropylapopinenes. Rates and Stoichiometry of the Hydroboration of 2-Organylapopinenes with Borane-Methyl Sulfide and Borane-Tetrahydrofuran

  摘要：

  Two higher analogues of Lu-pinene, 2-isobutyl- and 2-isopropylapopinenes, promising chiral auxiliaries for asymmetric hydroboration, were readily synthesized from alpha-pinene in good chemical yield. A quantitative study was made of the rates and stoichiometry of the hydroboration of a number of representative 2-organylapopinenes (2-R-apopinenes) with representative boranes, such as BH3.SMe(2) (BMS) and BH3.THF, in order to develop a convenient procedure for the synthesis of mono- and bis(2-organylapoisopinocampheyl)boranes [2-R-apoisopinylborane (RapBH(2)) and bis(2-R-apoisopinyl)borane (Rap(2)BH), respectively],under investigation as possible improved asymmetric hydroborating reagents. It was evident that the sterically bulkier 2-R-apopinenes such as 2-phenyl- and 2-isopropylapopinenes reacted with boranes at room temperature to form essentially RapBH(2) in greater than or equal to 195 % yield, while a yield of greater than or equal to 90 % was realized in the case of 2-isobutylapopinene; However, alpha-pinene, and 2-ethyl- and 2-n-propylapopinenes smoothly reacted with boranes to form a mixture of RapBH(2) and Rap(2)BH. Under the reaction conditions employed, 2-ethyl-, 2-n-propyl-, 2-isobutyl-, 2-phenyl-, and 2-isopropylapopinenes failed to produce clean Rap(2)BH. The rate of hydroboration decreased significantly with increase in bulk of the organyl group at the 2-position of the apopinene.

  DOI：

  10.1021/jo00087a016

文献信息

• [EN] S1P RECEPTORS MODULATORS AND THEIR USE THEREOF<br/>[FR] MODULATEURS DES RÉCEPTEURS S1P ET LEUR UTILISATION
  申请人：AKAAL PHARMA PTY LTD

  公开号：WO2010043000A1

  公开（公告）日：2010-04-22

  The invention relates to novel compounds that have S1P receptor modulating activity. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, autoimmune response. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as autoimmune response.

  这项发明涉及具有S1P受体调节活性的新化合物。此外，该发明涉及包括本发明中至少一种化合物的药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，例如自身免疫反应。该发明的另一个方面涉及使用包括本发明中至少一种化合物的药物制造药物，用于治疗由不当的S1P受体调节活性或表达引起或相关的疾病和/或病况，如自身免疫反应。
• S1P Receptors Modulators and Their Use Thereof
  申请人：Gill Gurmit S.

  公开号：US20110318388A1

  公开（公告）日：2011-12-29

  The invention relates to novel compounds that have S1P receptor modulating activity. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, autoimmune response. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as autoimmune response.

  本发明涉及具有S1P受体调节活性的新化合物。此外，本发明涉及包括本发明中至少一种化合物的药物，用于治疗由不适当的S1P受体调节活性或表达引起或相关的疾病和/或病情，例如自身免疫反应。本发明的另一个方面涉及使用包括本发明中至少一种化合物的药物制造药物，用于治疗由不适当的S1P受体调节活性或表达引起或相关的疾病和/或病情，例如自身免疫反应。
• S1P RECEPTORS MODULATORS AND THEIR USE THEREOF
  申请人：AKAAL PHARMA PTY LTD.

  公开号：US20160038455A1

  公开（公告）日：2016-02-11

  The invention relates to novel compounds that have S1P receptor modulating activity. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, autoimmune response. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as autoimmune response.

  本发明涉及具有S1P受体调节活性的新化合物。此外，本发明涉及一种制药组合物，包括本发明中的至少一种化合物，用于治疗由于或与不当的S1P受体调节活性或表达有关的疾病和/或病症，例如自身免疫反应。本发明的另一个方面涉及使用包括本发明中的至少一种化合物的制药组合物制造用于治疗由于或与不当的S1P受体调节活性或表达有关的疾病和/或病症，例如自身免疫反应的药物。
• Uzarewicz; Dresler; Scianowski, Polish Journal of Chemistry, 1998, vol. 72, # 4, p. 710 - 718
  作者：Uzarewicz、Dresler、Scianowski

  DOI：——

  日期：——
• S1P RECEPTORS MODULATORS AND USE THEREOF
  申请人：Akaal Pharma Pty Ltd

  公开号：EP2344484B1

  公开（公告）日：2016-06-08