(S,S)-1,3-bis(methanesulfonyloxy)-1,3-dicyclohexylpropane | 874297-56-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (S,S)-1,3-bis(methanesulfonyloxy)-1,3-dicyclohexylpropane
• 英文别名: [(1S,3S)-1,3-dicyclohexyl-3-methylsulfonyloxypropyl] methanesulfonate
• CAS: 874297-56-0
• 化学式: C₁₇H₃₂O₆S₂
• 分子量: 396.569
• InChiKey: PMVHMZTXIYHZDA-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S,S)-1,3-bis(methanesulfonyloxy)-1,3-dicyclohexylpropane 在 selenium 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  New chiral 1,3-diphosphine ligands for Rh-catalyzed enantioselective hydrogenation: a search for electronic effects

  摘要：

  New electron-rich chiral 1,3-diphosphines of the BDPP type were prepared from 1, 3-diphenylpropane- 1,3-diol by an economically feasible synthetic approach. The a-donor properties of the phosphines were determined by measurement of J(P-31-Se-77) coupling constants in the corresponding phosphine selenides. For comparison related, but electronically different, 1,3-diphosphines were considered. The new diphosphines showed good enantioselectivities as ligands in the Rh-catalyzed enantioselective hydrogenation of benchmark substrates and beta-amino acid precursors (up to 98% ee). The electronic effects on the outcome of the enantioselective catalysis have been analyzed. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.08.048
• 作为产物：
  描述：

  (1S,3S)-1,3-diphenylpropane-1,3-diol 在 rhodium(III) chloride 、 氢气 、 甲基三辛基氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 22.0h， 生成 (S,S)-1,3-bis(methanesulfonyloxy)-1,3-dicyclohexylpropane
  参考文献：
  名称：

  Synthesis of the C₂Symmetric 1,3-Dicyclohexyl-1,3-Propanediol and Diamine Enantiomers

  摘要：

  The parent C-2-symmetric (R,R)- and (S,S)-1,3-dicyclohexyl-1,3-propanediols and diamines are readily obtained from the corresponding diphenyldiol precursors.

  DOI：

  10.1080/00397919908086006

文献信息

• Synthesis of the C₂Symmetric 1,3-Dicyclohexyl-1,3-Propanediol and Diamine Enantiomers
  作者：A. Richard Donovan、Gregory H. P. Roos

  DOI：10.1080/00397919908086006

  日期：1999.11

  The parent C-2-symmetric (R,R)- and (S,S)-1,3-dicyclohexyl-1,3-propanediols and diamines are readily obtained from the corresponding diphenyldiol precursors.
• New chiral 1,3-diphosphine ligands for Rh-catalyzed enantioselective hydrogenation: a search for electronic effects
  作者：Natalia V. Dubrovina、Vitali I. Tararov、Axel Monsees、Anke Spannenberg、Ioannis D. Kostas、Armin Börner

  DOI：10.1016/j.tetasy.2005.08.048

  日期：2005.11

  New electron-rich chiral 1,3-diphosphines of the BDPP type were prepared from 1, 3-diphenylpropane- 1,3-diol by an economically feasible synthetic approach. The a-donor properties of the phosphines were determined by measurement of J(P-31-Se-77) coupling constants in the corresponding phosphine selenides. For comparison related, but electronically different, 1,3-diphosphines were considered. The new diphosphines showed good enantioselectivities as ligands in the Rh-catalyzed enantioselective hydrogenation of benchmark substrates and beta-amino acid precursors (up to 98% ee). The electronic effects on the outcome of the enantioselective catalysis have been analyzed. (c) 2005 Published by Elsevier Ltd.