(1R)-1-ethyl-7,7-dimethylbicyclo<2.2.1>heptan-2-one | 176022-22-3

• 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: (1R)-1-ethyl-7,7-dimethylbicyclo<2.2.1>heptan-2-one
• 英文别名: (1R,4R)-1-ethyl-7,7-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 176022-22-3
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: CLWLASGSYJVYJA-KCJUWKMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R)-1-ethyl-7,7-dimethylbicyclo<2.2.1>heptan-2-one 在 selenium(IV) oxide 作用下， 以 乙酸酐 为溶剂， 反应 72.0h， 以51%的产率得到(1R)-1-ethyl-7,7-dimethylbicyclo<2.2.1>heptan-2,3-dione
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries

  摘要：

  Transposition of the dormant methyl group from C-1 in chiral oxazolidin-2-one 2 to C-7 in a six step synthetic sequence from (1R)-camphor 5 creates a novel transfigomer 4 with sufficient pi-topological bias to induce excellent levels of asymmetric induction in Lewis-acid catalysed Diels-Alder reactions of its alpha,beta-unsaturated carboximide derivatives with cyclopentadiene. Further modification of 4 by replacement of the C-7 methyl group with an ethyl substituent raises the level of diastereoselectivity for the acrylate derivative 11a from 81 to >95% d.e..

  DOI：

  10.1016/s0040-4020(96)00070-1
• 作为产物：
  描述：

  在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 46.0h， 生成 (1R)-1-ethyl-7,7-dimethylbicyclo<2.2.1>heptan-2-one
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries

  摘要：

  Transposition of the dormant methyl group from C-1 in chiral oxazolidin-2-one 2 to C-7 in a six step synthetic sequence from (1R)-camphor 5 creates a novel transfigomer 4 with sufficient pi-topological bias to induce excellent levels of asymmetric induction in Lewis-acid catalysed Diels-Alder reactions of its alpha,beta-unsaturated carboximide derivatives with cyclopentadiene. Further modification of 4 by replacement of the C-7 methyl group with an ethyl substituent raises the level of diastereoselectivity for the acrylate derivative 11a from 81 to >95% d.e..

  DOI：

  10.1016/s0040-4020(96)00070-1

文献信息

• Highly Diastereoselective Aldol Reactions with Camphor-Based Acetate Enolate Equivalents
  作者：Claudio Palomo、Mikel Oiarbide、Jesús M. Aizpurua、Alberto González、Jesús M. García、Cristina Landa、Ibon Odriozola、Anthony Linden

  DOI：10.1021/jo990865z

  日期：1999.10.1

  New lithium enolates of alpha-hydroxy ketones, derived from camphor, are evaluated for asymmetric aldol reactions in the presence of lithium chloride. The diastereoselectivity of the reactions between the lithium enolate of 3 and a variety of achiral aldehydes is strongly influenced by the lithium chloride salt. In these instances, the achieved levels of asymmetric induction, typically 95:5 dr, are

  在氯化锂的存在下，对源自樟脑的新的α-羟基酮的烯醇锂进行了不对称羟醛反应的评估。氯化锂盐强烈影响3的烯醇锂和各种非手性醛之间反应的非对映选择性。在这些情况下，所达到的不对称诱导水平，通常为95：5 dr，在涉及甲基酮4的烯醇锂的羟醛反应中达到的范围内，这在空间上更加苛刻。所得的羟醛加合物容易转化为β-羟基羧酸，酮和醛，同时回收了樟脑，该方法的手性控制剂可以重复使用。
• NEW METHOD FOR THE PREPARATION OF HIGHLY PURE IVABRADINE BASE AND SALTS THEREOF
  申请人：URQUIMA, S.A

  公开号：US20180162820A1

  公开（公告）日：2018-06-14

  A method for the preparation of purified ivabradine and salts thereof, a method for the purification of ivabradine and salts thereof, a new reactant used in said methods and the use of said reactant for the preparation of ivabradine.
• Asymmetric Diels-Alder reactions employing modified camphor-derived oxazolidin-2-one chiral auxiliaries
  作者：Malcolm R. Banks、Alexander J. Blake、J.I.G. Cadogan、Allan A. Doyle、Ian Gosney、Philip K.G. Hodgson、Paul Thorburn

  DOI：10.1016/s0040-4020(96)00070-1

  日期：1996.3

  Transposition of the dormant methyl group from C-1 in chiral oxazolidin-2-one 2 to C-7 in a six step synthetic sequence from (1R)-camphor 5 creates a novel transfigomer 4 with sufficient pi-topological bias to induce excellent levels of asymmetric induction in Lewis-acid catalysed Diels-Alder reactions of its alpha,beta-unsaturated carboximide derivatives with cyclopentadiene. Further modification of 4 by replacement of the C-7 methyl group with an ethyl substituent raises the level of diastereoselectivity for the acrylate derivative 11a from 81 to >95% d.e..