anti-1,3-Diphenyl-2,3-epoxy-1-propanol

• 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: anti-1,3-Diphenyl-2,3-epoxy-1-propanol
• 英文别名: (R)-phenyl-[(2R,3R)-3-phenyloxiran-2-yl]methanol
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: XBZLYTRSFIMWRB-RBSFLKMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  anti-1,3-Diphenyl-2,3-epoxy-1-propanol 在 红铝 作用下， 以 乙二醇二甲醚 为溶剂， 反应 16.0h， 以91.5%的产率得到(1S,3S)-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
• 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 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 anti-1,3-Diphenyl-2,3-epoxy-1-propanol
  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

• Enantioselective One-Pot Catalytic Synthesis of 4,5-Epoxy-3-alkanols and 1-Phenyl-2,3-epoxy-1-alkanols from α,β-Unsaturated Aldehydes
  作者：Rebeca Infante、Yulan Hernández、Javier Nieto、Celia Andrés

  DOI：10.1002/ejoc.201300397

  日期：2013.8

  Conformationally restricted perhydrobenzoxazines have been demonstrated to be good chiral ligands for one-pot asymmetric ethylation/epoxidation, and the unprecedented arylation/epoxidation of trisubstituted α,β-unsaturated aldehydes. The scope of the reaction has been studied and a wide set of substrates with allylic strain of different nature has been explored, obtaining good or total diastereoselectivities

  构象受限的全氢苯并恶嗪已被证明是用于一锅不对称乙基化/环氧化和三取代 α,β-不饱和醛的前所未有的芳基化/环氧化的良好手性配体。已经研究了反应的范围，并探索了具有不同性质的烯丙基应变的广泛底物，在所有情况下都获得了良好的或完全的非对映选择性。乙基化/环氧化反应的对映控制良好或高，而芳基化/环氧化反应保持中等或良好水平。该反应对于三取代的烯醛是通用的，并且在不饱和醛的 α- 和 β- 位都可以容忍烷基和芳族取代基；然而，双取代的烯醛仍然是具有挑战性的底物。当比较一锅和两锅协议时，
• Asymmetric allylic substitution reaction with nitrogen and oxygen nucleophiles using monodentate chiral phosphine, 9-PBN
  作者：Yasumasa Hamada、Noriko Seto、Yoshie Takayanagi、Takeshi Nakano、Osamu Hara

  DOI：10.1016/s0040-4039(99)01617-2

  日期：1999.10

  Asymmetric allylic substitution reactions between 1,3-diphenyl-2-propenyl acetate and various hetero nucleophiles were efficiently carried out using the catalysts derived from the monodentate phosphine ligands, (1R, 2S, 5R, 6S)-2,6-dimethyl-9-phenyl-9-phosphabicyclo[3.3.1] nonane and its enantiomer ((−)- and (+)-9-PBNs), and palladium (0).

  使用衍生自单齿膦配体（1 R，2 S，5 R，6 S）-2,6的催化剂，可以有效地进行1,3-二苯基-2-丙烯基乙酸丙烯酯与各种杂亲核试剂之间的不对称烯丙基取代反应-二甲基-9-苯基-9-磷酸双环[3.3.1]壬烷及其对映异构体（（-）-和（+）-9-PBNs）和钯（0）。
• Chemo- and stereoselective reduction of α,β-epoxyketones with diisopropoxytitanium(III) tetrahydroborate
  作者：K.S Ravikumar、Srinivasan Chandrasekaran

  DOI：10.1016/0040-4020(96)00465-6

  日期：1996.7

  Reduction of α,β-epoxyketones with diisopropoxytitanium(III) tetrahydroborate in dichloromethane under mild conditions (−78° → −20°C) provides anti- (or erythro-) α,β-epoxy alcohols in high yields with high degree of chemo- and stereoselectivity.

  在温和的条件下（-78°→-20°C），用四氢硼酸二异丙氧基钛（III）在二氯甲烷中还原α，β-环氧酮可提供高收率的抗-（或赤型）α，β-环氧醇，且具有高度的化学反应性-和立体选择性。
• 10.1002/adsc.202400267
  作者：Shabade, Anand B.、Singh, Rahul K.、Gonnade, Rajesh G.、Punji, Benudhar

  DOI：10.1002/adsc.202400267

  日期：——

  Chemoselective hydrogenation of α,β-epoxy ketones and α-ketoamides is achieved at room temperature (25 °C) using 2.0 bar H2 and a pincer-ligated Mn(I) catalyst that provides synthetically valuable α-hydroxy epoxides and α-hydroxy amides. This protocol applies to a wide range of alkyl and aryl-substituted α,β-epoxy ketones, including terpenes (α-ionone, nootkatone, and R-carvone)- and steroids (testosterone

  使用 2.0 bar H 2和钳式连接的 Mn(I) 催化剂在室温 (25 °C) 下实现 α,β-环氧酮和 α-酮酰胺的化学选择性氢化，从而提供具有合成价值的 α-羟基环氧化物和 α-羟基酰胺。该方案适用于各种烷基和芳基取代的 α,β-环氧酮，包括萜烯（α-紫罗兰酮、nootkatone 和 R-香芹酮）和类固醇（睾酮和黄体酮）衍生的环氧酮，并且耐受 H 2敏感官能团，如卤化物、乙酰基、腈基、硝基、环氧基、烯基和炔基。此外，带有可还原官能团（包括乙酰基和重氮苯）的α-酮酰胺在此方案下未受影响，并选择性地转化为α-羟基酰胺。初步的机理研究强调了金属-配体协同H 2活化过程。
• NMR Studies of Three Types of Highly Coordinated Organotin Hydrides:  Chemo-, Regio-, and Stereoselective Reduction of 2,3-Epoxy Ketones
  作者：Takayo Kawakami、Ikuya Shibata、Akio Baba

  DOI：10.1021/jo9512416

  日期：1996.1.1

  Three types of highly coordinated organotin hydrides, Bu(2)SnIH-Lewis base (Lewis bases; HMPA or tripiperidinophosphine oxide) (type A), Bu(2)SnFH-HMPA (type B), and Bu(3)SnH-Bu(4)NX (X = F, CN) (type C), were characterized as nucleophilic, chelation, and nonchelation types of reductants, respectively, in the reaction with 2,3-epoxy ketones 1. These reagents, which promoted a reduction of the epoxy ring and syn-selective and anti-selective carbonyl reduction, respectively, were spectroscopically confirmed with H-1, C-13, F-19, and Sn-119 NMR and FT-IR. Furthermore, the correlations between their structures and selective reducing abilities were discussed.