(S)-2-hydroxy-1,2-diphenylpropan-1-one | 129263-06-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (S)-2-hydroxy-1,2-diphenylpropan-1-one
• 英文别名: (S)-2-Hydroxy-1,2-diphenyl-propan-1-on；(2S)-2-hydroxy-1,2-diphenylpropan-1-one
• CAS: 129263-06-5
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: DIVXVZXROTWKIH-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 (S)-2-hydroxy-1,2-diphenylpropan-1-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-1,2-diphenyl-2-((trimethylsilyl)oxy)propan-1-one
  参考文献：
  名称：

  Lanthanum Tricyanide-Catalyzed Acyl Silane−Ketone Benzoin Additions and Kinetic Resolution of Resultant α-Silyloxyketones

  摘要：

  We report the full account of our efforts on the lanthanum tricyanide-catalyzed acyl silane ketone benzoin reaction. The reaction exhibits a wide scope in both acyl silane (aryl, alkyl) and ketone (arylalkyl, alkyl-alkyl, aryl-aryl, alkenyl-alkyl, alkynyl-alkyl) coupling partners. The diastereoselectivity of the reaction has been examined in both cyclic and acyclic systems. Cyclohexanones give products arising from equatorial attack by the acyl silane. The diastereoselectivity of acyl silane addition to acyclic alpha-hydroxy ketones can be controlled by varying the protecting group to obtain either Felkin-Ahn or chelation control. The resultant alpha-silyloxyketone products can be resolved with selectivity factors from 10 to 15 by subjecting racemic ketone benzoin products to CBS reduction.

  DOI：

  10.1021/jo100312w
• 作为产物：
  描述：

  (S)-(+)-2-羟基-2-苯丙酸 在 ammonium hydroxide 、 乙醚 作用下， 生成 (S)-2-hydroxy-1,2-diphenylpropan-1-one
  参考文献：
  名称：

  Extent and Severity of Groundwater Arsenic Contamination in Bangladesh

  摘要：

  DOI：

  10.1080/02508060108686929

文献信息

• Isothiourea‐Catalyzed Acylative Kinetic Resolution of Tertiary α‐Hydroxy Esters
  作者：Shen Qu、Samuel M. Smith、Víctor Laina‐Martín、Rifahath M. Neyyappadath、Mark D. Greenhalgh、Andrew D. Smith

  DOI：10.1002/anie.202004354

  日期：2020.9.14

  acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols

  已开发出高度对映选择性的异硫脲催化的无环叔醇的酰基动力学拆分（KR）。对于带有相邻酯取代基的叔醇的KR，选择性因子高达200，反应转化率和对映体选择性均对立体异构叔丁醇中心的空间和电子环境敏感。对于空间上更拥挤的醇，最合适的方法是使用最新开发的异硒脲催化剂，对映选择性相当，但与异硫脲HyperBTM相比，转化率更高。非对映体酰化过渡态模型被提出以合理化此过程中对映歧化的起源。
• Environmental Management Systems in Outdoor Recreation: A Case Study of a Forest Enterprise (UK) Site
  作者：Xavier Font、Patricia Flynn、John Tribe、Karen Yale

  DOI：10.1080/09669580108667388

  日期：2001.5.30
• Studies in Stereochemistry. XXX. Models for Steric Control of Asymmetric Induction¹
  作者：Donald J. Cram、Karl R. Kopecky

  DOI：10.1021/ja01520a036

  日期：1959.6
• Catalytic asymmetric dihydroxylation of tetrasubstituted olefins
  作者：Kouhei Morikawa、Jeonghan Park、Pher G. Andersson、Tomiki Hashiyama、K. Barry Sharpless

  DOI：10.1021/ja00071a072

  日期：1993.9
• Phase-Transfer-Catalyzed Enantioselective α-Hydroxylation of Acyclic and Cyclic Ketones with Oxygen
  作者：Sui-Boon Derek Sim、Min Wang、Yu Zhao

  DOI：10.1021/acscatal.5b00583

  日期：2015.6.5

  An efficient and enantioselective alpha-hydroxylation of acyclic as well as cyclic ketones using molecular oxygen has been developed. This simple catalytic procedure uses a readily available phase transfer catalyst and produces a wide range of valuable tertiary a-hydroxy ketones in good to excellent enantiopurity.