(1S,4S,5R,6R)-6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one | 1131282-69-3

• 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,4S,5R,6R)-6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one
• CAS: 1131282-69-3
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: VBYAEPOBIZACRL-XCCSTKFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以45%的产率得到(1S,4S,5R,6R)-6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one
  参考文献：
  名称：

  烯胺介导的醛与环状烯酮的加成反应

  摘要：

  描述了O-三甲基甲硅烷基化的α，α-二苯基脯氨醇催化的醛向环状不饱和烯酮的加成。讨论了明显异常的立体化学结果。

  DOI：

  10.1002/adsc.201000755

文献信息

• PREPARATION OF BICYCLO[2.2.2]OCTAN-2-ONE COMPOUNDS
  申请人：Abele Stefan

  公开号：US20130211104A1

  公开（公告）日：2013-08-15

  The present invention relates to a new process for the preparation of 6-hydroxy-5-arylbicyclo[2.2.2]octan-2-one compounds of the formula (II); which may subsequently be further transformed to compounds of the formula (I): The present invention further relates to novel compounds as such, which compounds are useful intermediates in the above process.

  本发明涉及一种制备公式（II）的6-羟基-5-芳基双环[2.2.2]辛烷-2-酮化合物的新工艺，该化合物随后可进一步转化为公式（I）的化合物： 本发明还涉及上述过程中有用的新化合物作为中间体。
• [EN] DIASTEREOSELECTIVE PREPARATION OF BICYCLO[2.2.2]OCTAN-2-ONE COMPOUNDS<br/>[FR] PRÉPARATION DIASTÉRÉOSÉLECTIVE DE COMPOSÉS BICYCLO[2.2.2]OCTAN-2-ONES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2012052943A1

  公开（公告）日：2012-04-26

  The present invention relates to a new process for the diastereoselective preparation of (1R*,4R*,5S*,6S*)-6-hydroxy-5-arylbicyclo[2.2.2]octan-2-one compounds, the compounds of the formula (II), which may subsequently be further transformed to 5-aryl-bicyclo[2.2.2]oct-5-en-2-one compounds of the formula (I): Formula (I), Formula (II). The present invention further relates to novel (1R*,2S*,3S*,4R*)-6-oxo-3-arylbicyclo[2.2.2]octan-2-yl methanesulfonate compounds as such, which compounds are useful intermediates in the preparation of 5-aryl-bicyclo[2.2.2]oct-5-en-2-one compounds of the formula (I).

  本发明涉及一种新的过程，用于对(1R*，4R*，5S*，6S*)-6-羟基-5-芳基双环[2.2.2]辛烷-2-酮化合物进行对映选择性制备，该化合物为公式(II)的化合物，该化合物随后可以进一步转化为公式(I)的5-芳基双环[2.2.2]辛-5-烯-2-酮化合物。本发明还涉及新的(1R*，2S*，3S*，4R*)-6-氧代-3-芳基双环[2.2.2]辛烷-2-甲磺酸酯化合物，这些化合物本身就是有用的中间体，用于制备公式(I)的5-芳基双环[2.2.2]辛-5-烯-2-酮化合物。
• DIASTEREOSELECTIVE PREPARATION OF BICYCLO[2.2.2]OCTAN-2-ONE COMPOUNDS
  申请人：Abele Stefan

  公开号：US20130289295A1

  公开（公告）日：2013-10-31

  The present invention relates to a new process for the diastereoselective preparation of (1R*,4R*,5S*,6S*)-6-hydroxy-5-arylbicyclo[2.2.2]octan-2-one compounds, the compounds of the formula (II), which may subsequently be further transformed to 5-aryl-bicyclo[2.2.2]oct-5-en-2-one compounds of the formula (I): The present invention further relates to novel (1R*,2S*,3S*,4R*)-6-oxo-3-arylbicyclo[2.2.2]octan-2-yl methanesulfonate compounds as such, which compounds are useful intermediates in the preparation of 5-aryl-bicyclo[2.2.2]oct-5-en-2-one compounds of the formula (I).

  本发明涉及一种新的过程，用于选择性地制备(1R*，4R*，5S*，6S*)-6-羟基-5-芳基双环[2.2.2]辛-2-酮化合物，即式(II)的化合物，该化合物随后可以进一步转化为式(I)的5-芳基双环[2.2.2]辛-5-烯-2-酮化合物：本发明还涉及新型(1R*，2S*，3S*，4R*)-6-氧代-3-芳基双环[2.2.2]辛-2-基甲磺酸酯化合物，这些化合物本身就是有用的中间体，用于制备式(I)的5-芳基双环[2.2.2]辛-5-烯-2-酮化合物。
• Diastereoselective preparation of bicyclo[2.2.2]octan-2-one compounds
  申请人：Abele Stefan

  公开号：US08816118B2

  公开（公告）日：2014-08-26

  The present invention relates to a new process for the diastereoselective preparation of (1R*,4R*,5S*,6S*)-6-hydroxy-5-arylbicyclo[2.2.2]octan-2-one compounds, the compounds of the formula (II), which may subsequently be further transformed to 5-aryl-bicyclo[2.2.2]oct-5-en-2-one compounds of the formula (I): The present invention further relates to novel (1R*,2S*,3S*,4R*)-6-oxo-3-arylbicyclo[2.2.2]octan-2-yl methanesulfonate compounds as such, which compounds are useful intermediates in the preparation of 5-aryl-bicyclo[2.2.2]oct-5-en-2-one compounds of the formula (I).

  本发明涉及一种新的选择性不对映异构体合成(1R*,4R*,5S*,6S*)-6-羟基-5-芳基双环[2.2.2]辛-2-酮化合物的方法，该化合物的化学式为(II)，该化合物随后可以进一步转化为化学式为(I)的5-芳基双环[2.2.2]辛-5-烯-2-酮化合物。本发明还涉及新的(1R*,2S*,3S*,4R*)-6-氧代-3-芳基双环[2.2.2]辛-2-基甲磺酸酯化合物，这些化合物本身是有用的中间体，可用于制备化学式为(I)的5-芳基双环[2.2.2]辛-5-烯-2-酮化合物。
• Scalable Synthesis of Enantiomerically Pure Bicyclo[2.2.2]octadiene Ligands
  作者：Stefan Abele、Roman Inauen、Dirk Spielvogel、Christian Moessner

  DOI：10.1021/jo3005638

  日期：2012.5.18

  An operationally simple and scalable synthesis of enantiomerically pure bicyclo[2.2.2]octadiene (bod*) ligands relying on an organocatalytic one-pot Michael addition-aldol reaction with cheap 2-cyclohexenone and phenylacetaldehyde is presented. The crystalline bicyclic product 4a (6-hydroxy-5-phenylbicyclo[2.2.2]octan-2-one) is transformed into phenylbicyclo[2.2.2]oct-5-en-2-one 2, a versatile starting material for the 2-step synthesis of both symmetrical, such as Hayashi's Ph-bod* ligand, as well as novel unsymmetrical chiral dienes.