1,3-二苯基-1,3-二羟基丙烷 | 5381-86-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 中文名称: 1,3-二苯基-1,3-二羟基丙烷
• 英文名称: (1R,3S)-1,3-diphenylpropane-1,3-diol
• 英文别名: meso-1,3-diphenylpropane-1,3-diol；meso-1,3-diphenyl-1,3-propanediol；1,3-diphenyl-1,3-propanediol；(1S,3R)-1,3-Diphenylpropane-1,3-diol
• CAS: 5381-86-2
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: XHHXJXGIYFQFOQ-GASCZTMLSA-N

物化性质

• 熔点：
  108-109 °C(Solv: benzene (71-43-2))
• 沸点：
  408.8±40.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-二苯基-1,3-二羟基丙烷 在 Cp* Ir[(S,S)-Msdpen] 作用下， 以 四氢呋喃 为溶剂， 30.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 以31%的产率得到(R)-3-hydroxy-1,3-diphenylpropane-1-one
  参考文献：
  名称：

  Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands

  摘要：

  Asymmetric aerobic oxidation of a range of meso- and prochiral diols with chiral bifunctional Ir catalysts is described. A high level of chiral discrimination ability of Cp*Ir complexes derived from (S,S)-1,2-diphenylethylenediamine was successfully demonstrated by desymmetrization of secondary benzylic diols such as cis-indan-1,3-diol and cis-1,4-diphenylbutane-1,4-diol, providing the corresponding (R)-hydroxyl ketones with excellent chemo- and enantioselectivities. Enantiotopic group discrimination in oxidation of symmetrical primary 1,4- and 1,5-diols gave rise to chiral lactones with moderate ees under similar aerobic conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.103
• 作为产物：
  描述：

  二苯甲酰基甲烷 在 吡啶 、 吡啶硼烷 、 四氯化钛 、 sodium hydroxide 、 双氧水 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 反应 6.0h， 以45%的产率得到1,3-二苯基-1,3-二羟基丙烷
  参考文献：
  名称：

  TiCl₄-Mediated Reduction of 1,3-Diketones with BH₃−Pyridine Complex:  A Highly Diastereoselective Method for the Synthesis of syn-1,3-Diols

  摘要：

  [GRAPHICS]1,3-Diketones can be reduced in high yields and with excellent diastereoselectivity to the corresponding syn-1,3-diols by carrying out the reaction with BH3-pyridine complex in CH2Cl2 at -78 degrees C in the presence of an equivalent of TiCl4 and 0.1 equiv of pyridine. This protocol shows a general character: excellent results are obtained when the groups bound to the carbonylic functions are linear or branched carbon chains and aromatic or benzylic frameworks as well.

  DOI：

  10.1021/ol991185l

文献信息

• Cascade Reaction by Chemo- and Biocatalytic Approaches to Obtain Chiral Hydroxy Ketones and <i>anti</i> 1,3-Diols
  作者：Raffaella Gandolfi、Giorgio Facchetti、Michael S. Christodoulou、Marco Fusè、Fiorella Meneghetti、Isabella Rimoldi

  DOI：10.1002/open.201800056

  日期：2018.5

  biocatalytic cascade approach was applied for the stereoselective synthesis of hydroxy ketones and the corresponding 1,3‐diols. A new class of tridentate N,N,O ligands was used with copper(II) complexes for the asymmetric β‐borylation of α,β‐unsaturated compounds. The complex containing ligand L5 emerged as the best performer, and it gave the organoborane derivatives with good ee values. The corresponding keto–alcohol

  化学和生物催化级联方法用于羟基酮和相应的1,3-二醇的立体选择性合成。一类新的三齿N，N，O配体与铜（II）配合物一起用于α，β-不饱和化合物的不对称β-硼化。含有配体L5的配合物表现出最好的表现，它使有机硼烷衍生物具有良好的ee值。相应的酮醇化合物随后被酵母生物还原。生物转化设置与深红酵母允许（[R ）酮醇和（小号，小号）-diols要与高达99％得到的 ee值和高达99％的 德赞成抗对映体。
• Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent
  作者：Matthew H. Gieuw、Zhihai Ke、Ying-Yeung Yeung

  DOI：10.1002/anie.201713422

  日期：2018.3.26

  A facile and effective system has been developed for the regio‐ and chemoselective ring‐opening/electrophilic functionalization of cyclopropanes through C−C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p‐toluenesulfonamide. The p‐toluenesulfonamide‐promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3‐diol products

  已经开发了一种简便有效的系统，借助路易斯（Lewis）碱性促进剂对甲苯磺酰胺，通过[双（三氟乙酰氧基）碘]苯的CC键活化，对环丙烷的区域和化学选择性开环/亲电子官能化。所述p -toluenesulfonamide促进的系统可以很好地用于宽范围的环丙烷，得到1,3-二醇产物以良好产率选择性和区域选择性的形成。
• Enantioselective Borohydride Reduction Catalyzed by Optically Active Cobalt Complexes
  作者：Tohru Yamada、Takushi Nagata、Kiyoaki D. Sugi、Kiyotaka Yorozu、Taketo Ikeno、Yuhki Ohtsuka、Daichi Miyazaki、Teruaki Mukaiyama

  DOI：10.1002/chem.200304794

  日期：2003.9.22

  enantioselective borohydride reduction of aromatic ketones or imines to the corresponding alcohols was developed in the presence of a catalytic amount of an optically active cobalt(II) complex catalyst. This enantioselective reduction is carried out using a precisely premodified borohydride with alcohols such as tetrahydrofurfuryl alcohol, ethanol and methanol. High optical yields are obtained by choosing

  在催化量的光学活性钴（II）络合物催化剂的存在下，芳香族酮或亚胺对映体的高度对映选择性硼氢化物还原。该对映选择性还原是使用精确预改性的硼氢化物与醇（例如四氢糠醇，乙醇和甲醇）进行的。通过选择合适的醇作为改性剂和合适的催化剂β-酮亚氨基配体，可以获得高的光学收率。对映选择性硼氢化物还原已成功应用于光学活性的1,3-二醇的制备，双酰基二茂铁的立体选择性还原以及1,3-二羰基化合物的动态和/或动力学拆分。
• Design, Reactivities, and Practical Application of Dialkylzinc Hydride Ate Complexes Generated <i>in Situ</i> from Dialkylzinc and Metal Hydride. A New Methodology for Activation of NaH and LiH under Mild Conditions
  作者：Masanobu Uchiyama、Shozo Furumoto、Mariko Saito、Yoshinori Kondo、Takao Sakamoto

  DOI：10.1021/ja9718477

  日期：1997.11.1

  dialkylzinc hydride “ate” complexes, prepared from dialkylzinc and metal hydride, and investigated the reactivities (and the transference aptitude of ligands) of these zincates toward benzophenone. The results clearly reveal that dimethylzinc hydrides are the most powerful and selective zincates for the reduction of the carbonyl group. This complex reagent turned out to be effective for the reduction of esters

  我们设计了各种由二烷基锌和金属氢化物制备的二烷基氢化锌“ate”配合物，并研究了这些锌酸盐对二苯甲酮的反应性（和配体的转移能力）。结果清楚地表明，二甲基氢化锌是还原羰基的最有效和选择性的锌酸盐。事实证明，这种复杂的试剂可有效地将酯和酰胺以及醛和酮还原为相应的醇和胺，并且在温和条件下具有良好到极好的收率。此外，该方法成功地用于α,β-不饱和羰基化合物的高选择性1,2-还原、环氧化物的区域选择性开环还原以及在酮存在下醛的化学选择性还原。我们还讨论和阐明活性物质和这种还原的机制，使用一些具有相邻手性中心的羰基化合物的非对映选择性还原。还有，这...
• Palladium-Catalyzed Aerobic Oxidative Kinetic Resolution of Alcohols with an Achiral Exogenous Base
  作者：Sunil K. Mandal、Matthew S. Sigman

  DOI：10.1021/jo034717r

  日期：2003.9.1

  (-)-sparteine for a more practical achiral base in the aerobic oxidative kinetic resolution of secondary alcohols is described. Carbonate bases are the most effective of those screened and allow for effective kinetic resolution of benzylic, allylic, and aliphatic substrates. The procedure was also successfully extended to the oxidative desymmetrization of meso diols.

  描述了在仲醇的有氧氧化动力学拆分中，将外源（-）-天冬氨酸替换为更实用的非手性碱。碳酸盐碱是所筛选的碱中最有效的碱，并可以有效地动力学分离苄基，烯丙基和脂肪族底物。该程序也成功地扩展到内消旋二醇的氧化脱对称。