[(1R,2R,3S)-2-(bromomethyl)-2,3-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]methyl-4-methylbenzenesulfonate | 497262-01-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1R,2R,3S)-2-(bromomethyl)-2,3-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]methyl-4-methylbenzenesulfonate
• 英文别名: (1S,2R,3R)-(2-bromomethyl-2,3-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl)-methyl 4-methylbenzenesulfonate；[(1S,2R,3R)-2-(bromomethyl)-2,3-dimethyl-3-(oxan-2-yloxymethyl)cyclopentyl]methyl 4-methylbenzenesulfonate
• CAS: 497262-01-8
• 化学式: C₂₂H₃₃BrO₅S
• 分子量: 489.471
• InChiKey: AQXLNHUOFGUSQA-ANQZQGJXSA-N

物化性质

• 沸点：
  559.8±40.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1R,2R,3S)-2-(bromomethyl)-2,3-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]methyl-4-methylbenzenesulfonate 在 4-甲基苯磺酸吡啶 、 lithium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.5h， 生成 [(1R,2R,3S)-(+)-1,2-二甲基-2,3-二(二苯基胺基甲基)环戊]甲醇
  参考文献：
  名称：

  A new hydroxydiphosphine as a ligand for Rh(I)-catalyzed enantioselective hydrogenation

  摘要：

  A new diphosphine ligand bearing a hydroxy group in the backbone was synthesized starting from 9-bromocamphor. The rhodium(I) complex based on this ligand was tested in the hydrogenation of alpha- and beta-amino acid precursors. The activity and selectivity of the catalyst were found to be strongly dependent upon the nature of the substrate. Thus. beta-acetylamino carboxylates were obtained with up to 97% ee. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00372-5
• 作为产物：
  描述：

  (1R,5R,8R)-8-(bromomethyl)-1,8-dimethyl-3-oxabicyclo[3.2.1]octane-2-one 在 吡啶 、 lithium aluminium tetrahydride 、 4-甲基苯磺酸吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(1R,2R,3S)-2-(bromomethyl)-2,3-dimethyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]methyl-4-methylbenzenesulfonate
  参考文献：
  名称：

  A new hydroxydiphosphine as a ligand for Rh(I)-catalyzed enantioselective hydrogenation

  摘要：

  A new diphosphine ligand bearing a hydroxy group in the backbone was synthesized starting from 9-bromocamphor. The rhodium(I) complex based on this ligand was tested in the hydrogenation of alpha- and beta-amino acid precursors. The activity and selectivity of the catalyst were found to be strongly dependent upon the nature of the substrate. Thus. beta-acetylamino carboxylates were obtained with up to 97% ee. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00372-5

文献信息

• [DE] HYDROXYDIPHOSPHINE UND DEREN VERWENDUNG IN DER KATALYSE<br/>[EN] HYDROXY DIPHOSPHINES AND THEIR USE IN CATALYSIS<br/>[FR] HYDROXYDIPHOSPHINES ET LEUR UTILISATION EN CATALYSE
  申请人：DEGUSSA

  公开号：WO2003099832A1

  公开（公告）日：2003-12-04

  Die Erfindung betrifft neue unsymmetrische chirale Hydroxydiphosphine und deren Derivate der allgemeinen Formel (I), sowie deren Verwendung als Katalysatoren, insbesondere für enantioselektive Synthesen.

  这项发明涉及新的不对称手性羟基二膦和其衍生物，其一般式为(I)，以及它们作为催化剂的应用，特别是用于对映选择性合成。
• CHIRAL INTERMEDIATES USEFUL FOR THE PREPARATION OF HYDROXYPHOSPHINE LIGANDS
  申请人：Shroff Jaidev Rajnikant

  公开号：US20130217900A1

  公开（公告）日：2013-08-22

  A compound of formula (I), wherein R 1 is hydrogen or a hydroxyl protecting group; and R 2 and R 3 are same or different and are independently selected from halogen or —O—SO 2 —X; wherein X is —C 1 -C 4 alkyl; C 1 -C 4 alkyl substituted with one or more halogen; or substituted or unsubstituted phenyl wherein said phenyl substituent is selected from halogen, nitro and C 1 -C 4 alkyl; provided that when R 3 is bromine, X is not p-toluoyl; and a process for the preparation thereof.

  公式（I）的化合物，其中R1是氢或羟基保护基；R2和R3相同或不同，且独立地选择自卤素或—O—SO2—X；其中X是—C1-C4烷基；C1-C4烷基被一个或多个卤素取代；或被取代或未取代的苯基，其中所述苯基取代基被选择自卤素、硝基和C1-C4烷基；但当R3为溴时，X不是对甲苯基；以及其制备方法。
• A new hydroxydiphosphine as a ligand for Rh(I)-catalyzed enantioselective hydrogenation
  作者：Igor V. Komarov、Axel Monsees、Renat Kadyrov、Christine Fischer、Ute Schmidt、Armin Börner

  DOI：10.1016/s0957-4166(02)00372-5

  日期：2002.8

  A new diphosphine ligand bearing a hydroxy group in the backbone was synthesized starting from 9-bromocamphor. The rhodium(I) complex based on this ligand was tested in the hydrogenation of alpha- and beta-amino acid precursors. The activity and selectivity of the catalyst were found to be strongly dependent upon the nature of the substrate. Thus. beta-acetylamino carboxylates were obtained with up to 97% ee. (C) 2002 Published by Elsevier Science Ltd.