(S,S)-methanesulfonyloxy-1,3-diphenylpropane-1,3-diol | 623932-48-9

• 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: (S,S)-methanesulfonyloxy-1,3-diphenylpropane-1,3-diol
• 英文别名: [(1S,3S)-3-methylsulfonyloxy-1,3-diphenylpropyl] methanesulfonate
• CAS: 623932-48-9
• 化学式: C₁₇H₂₀O₆S₂
• 分子量: 384.474
• InChiKey: BNPFBQBQCYPKJU-IRXDYDNUSA-N

物化性质

• 熔点：
  62-63 °C (decomp)
• 沸点：
  607.6±55.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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)-methanesulfonyloxy-1,3-diphenylpropane-1,3-diol 在 lithium aluminium tetrahydride 、 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 racemic 1,3-diphenyl-1,3-propanediamine
  参考文献：
  名称：

  Synthesis of novel C2-symmetric ligands based on (R,R)- and (S,S)-diphenyl-1,3-propanediol

  摘要：

  A range of novel Ct-symmetric dioxygen and dinitrogen ligands can readily be obtained through the interconversion of the parent 1,3-diphenyl-1,3-propanediol enantiomers which are, in turn, accessed in good yields via a Sharpless asymmetric epoxidative resolution. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00074-9
• 作为产物：
  描述：

  反-1,3-二苯基-2-丙稀-1-醇 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 3 A molecular sieve 、 D-(-)-酒石酸二异丙酯 、 三乙胺 、 红铝 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 (S,S)-methanesulfonyloxy-1,3-diphenylpropane-1,3-diol
  参考文献：
  名称：

  Synthesis of novel C2-symmetric ligands based on (R,R)- and (S,S)-diphenyl-1,3-propanediol

  摘要：

  A range of novel Ct-symmetric dioxygen and dinitrogen ligands can readily be obtained through the interconversion of the parent 1,3-diphenyl-1,3-propanediol enantiomers which are, in turn, accessed in good yields via a Sharpless asymmetric epoxidative resolution. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00074-9

文献信息

• A Diastereodivergent and Enantioselective Approach to <i>syn</i>- and <i>anti</i>-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines
  作者：Pengfei Zhou、Xinxin Shao、Steven J. Malcolmson

  DOI：10.1021/jacs.1c07707

  日期：2021.9.1

  catalytic enantioselective synthesis of allylic amines. Herein, we demonstrate their promise by a diastereodivergent synthesis of syn- and anti-1,2-diamines through their Cu–bis(phosphine)-catalyzed reductive couplings with imines. With Ph-BPE as the supporting ligand, anti-diamines are obtained (up to 91% yield, >20:1 dr, and >99:1 er), and with the rarely utilized t-Bu-BDPP, syn-diamines are generated (up

  我们介绍了一种新的试剂类 2-氮杂三烯，作为催化对映选择性合成烯丙基胺的平台。在这里，我们通过铜-双（膦）催化的与亚胺的还原偶联，通过非对映异构合成顺-和反-1,2-二胺来证明它们的前景。以 Ph-BPE 作为支持配体，得到反二胺（高达 91% 的产率，>20:1 dr，和 >99:1 er），而使用很少使用的t -Bu-BDPP，顺二胺是生成（高达 76% 的产率，1:>20 dr 和 97:3 er）。
• Diphosphine sulfides derived from 2,2′-biphosphole: novel chiral S,S ligands for palladium-catalyzed asymmetric allylic substitution
  作者：Emmanuel Robé、Wieslawa Perlikowska、Céline Lemoine、Lisa Diab、Sandrine Vincendeau、Marian Mikolajczyk、Jean-Claude Daran、Maryse Gouygou

  DOI：10.1039/b719554k

  日期：——

  Diphosphine sulfides derived from 2,2′-biphosphole have been efficiently synthesized in an enantiomerically pure form by a four step synthetic sequence. These S,S-ligands were used for the first time in Pd-catalyzed asymmetric allylic alkylation. Good yields and enantiomeric excess up to 73% were obtained.

  通过四步合成顺序，我们高效合成了对映体纯度为 2,2â²-联磷的二膦硫化物。这些 S,S 配体首次用于 Pd 催化的不对称烯丙基烷基化反应。获得了良好的产率和高达 73% 的对映体过剩率。
• Economic preparation of 1,3-diphenyl-1,3-bis(diphenylphosphino)propane: a versatile chiral diphosphine ligand for enantioselective hydrogenations
  作者：Natalia V. Dubrovina、Vitali I. Tararov、Axel Monsees、Renat Kadyrov、Christine Fischer、Armin Börner

  DOI：10.1016/s0957-4166(03)00595-0

  日期：2003.9

  The enantioselective hydrogenation of 1,3-diarylpropane-1,3-diones with chiral Ru(II)-diphosphine catalyst has been studied. In a first approach it was found, that Tol-BINAP together with Ru(COD)methallyl(2) formed the most selective catalyst. One of the C-2-symmetric enantiopure 1,3-diols obtained in turn was transformed via its 1,3-di-O-mesylate into 1,3-bisdiarylphosphines. One of them, 1,3-diphenyl-1,3-bis(diphenylphosphino)propane, could be advantageously utilized as a ligand for the efficient enantioselective Ru-catalyzed hydrogenation of its own 1,3-diketone precursor. Thus, the condition for a 'cross self-breeding' catalytic system is fulfilled. A further reduction of the preparation costs could be achived by application of RuCl3.H2O instead of other more expensive precatalyst precursors without compromosing the enantioselectivity. The ligand was used in the Rh(I)-catalyzed asymmetric hydrogenation of model substrates and beta-amino acid precursors where up to 97% ee could be achieved. (C) 2003 Elsevier Ltd. All rights reserved.