(1R,2R)-2,3-epoxy-1-phenylpropan-1-ol | 146388-55-8

• 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: (1R,2R)-2,3-epoxy-1-phenylpropan-1-ol
• 英文别名: (1R,2R)-phenyl-2,3-glycidol；(1R,2R)-1-phenylglycidol；(R)-[(2R)-oxiran-2-yl]-phenylmethanol
• CAS: 146388-55-8
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: QHUCJYPNJYZEOQ-RKDXNWHRSA-N

物化性质

• 沸点：
  269.7±13.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (1R,2R)-2,3-epoxy-1-phenylpropan-1-ol 在 lithium aluminium tetrahydride 作用下， 以64%的产率得到(1R,2R)-1-phenylpropane-1,2-diol
  参考文献：
  名称：

  Enzymatic preparation of chiral 1-phenylglycidols and 1-phenyl-1,2-propanediols

  摘要：

  Asymmetric synthesis of chiral 1-phenylglycidols and the O-acetates, which were expected to be useful intermediates for the synthesis of beta-blockers, has been achieved effectively by use of baker's yeast and lipase PS. These chiral epoxides could be reduced regioselectively with lithium aluminium hydride to give chiral 1-phenyl- 1,2-propanediols.

  DOI：

  10.1016/0957-4166(92)80008-k
• 作为产物：
  描述：

  1-苯基-2-丙烯基-1-酮 在 glucose dehydrogenase 、 葡萄糖 、 styrene monooxygenase 、 ChKRED₀₃ DNA from Chryseo bacterium 、 nicotinamide adenine dinucleotide phosphate 作用下， 以 aq. phosphate buffer 为溶剂， 反应 3.0h， 生成 (1R,2R)-2,3-epoxy-1-phenylpropan-1-ol
  参考文献：
  名称：

  Synthesis of enantiopure glycidol derivatives via a one-pot two-step enzymatic cascade

  摘要：

  描述了一种使用特异性酮还原酶和苯乙烯单加氧酶进行酶级级联反应以合成对映纯的环氧乙烷衍生物的方法。

  DOI：

  10.1039/c4ob02186j

文献信息

• Highly diastereo- and enantio-selective epoxidation of secondary allylic alcohols catalyzed by styrene monooxygenase
  作者：Hui Lin、Yan Liu、Zhong-Liu Wu

  DOI：10.1039/c0cc04360e

  日期：——

  Enantiomerically enriched glycidol derivatives with contiguous stereogenic centers were obtained in a highly diastereo- and enantio-selective epoxidation catalyzed with the styrene monooxygenase StyAB2.

  在以苯乙烯单加氧酶StyAB2作为催化剂的高度立体选择性和对映选择性环氧化反应中，获得了具有相邻立体中心的高对映体富集的缩水甘油衍生物。
• A new monooxygenase from <i>Herbaspirillum huttiense</i> catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols
  作者：Hui Lin、Yanhong Tang、Shuang Dong、Ruibo Lang、Hongge Chen

  DOI：10.1039/d0cy00081g

  日期：——

  epoxidation could also achieve the kinetic resolution of racemic secondary allylic alcohols, yielding the corresponding epoxides with up to 50% yields, as well as excellent enantio- and diastereoselectivity (up to >99% ee and >99% de) within 20–60 min, making a greener strategy for the production of valuable enantiopure glycidol derivatives in the fine chemical and pharmaceutical industries.

  不对称环氧化是制备对映纯环氧化物的绿色途径，但通常对未共轭末端烯烃的对映选择性低。基于六个苯乙烯单加氧酶的祖先序列重构的NCBI非冗余蛋白序列的挖掘，从胡氏螺旋藻中鉴定出单加氧酶（HhMo）与苯乙烯单加氧酶具有29.6–32.3％的序列同一性，以前被标注为丙氨酸磷酸核糖醇连接酶。HhMo以中等至优异的对映选择性催化烯丙基苯的环氧化反应，可产生高达99％ee的相应环氧化物。HhMo催化的环氧化还可以实现外消旋仲烯丙醇的动力学拆分，得到相应的环氧化物，其收率高达50％，并且在其中具有出色的对映和非对映选择性（高达> 99％ee和> 99％de） 20–60分钟，为精细化工和制药业生产有价值的对映纯缩水甘油缩水甘油酯制定了更环保的策略。
• <i>syn</i> ‐Selective Epoxidation of Chiral Terminal Allylic Alcohols with a Titanium Salalen Catalyst and Hydrogen Peroxide
  作者：Fabian Severin、Giovanni M. Fusi、Christina Wartmann、Jörg‐Martin Neudörfl、Albrecht Berkessel

  DOI：10.1002/anie.202201790

  日期：2022.6.27

  asymmetric epoxidation/kinetic resolution provides access to anti-configured terminal epoxy alcohols with high selectivity, no analogous syn-selective epoxidation process has been available. We report that this “missing link” is provided by a readily available titanium salalen catalyst. Besides allylic alcohols, allylic ethers are epoxidized with extreme syn-selectivity, at low catalyst loading, with

  虽然 Sharpless 不对称环氧化/动力学拆分提供了以高选择性获得反构型末端环氧醇的途径，但目前还没有类似的顺选择性环氧化工艺。我们报告说，这种“缺失的环节”是由现成的钛 salalen 催化剂提供的。除了烯丙醇外，烯丙醚在低催化剂负载下以极高的顺式选择性环氧化，使用水性 H 2 O 2作为氧化剂。
• Asymmetric dihydroxylation of primary allylic halides and a concise synthesis of (−)-diepoxybutane
  作者：Koen P.M. Vanhessche、Zhi-Min Wang、K.Barry Sharpless

  DOI：10.1016/s0040-4039(00)73212-6

  日期：1994.5

  Tire asymmetric dihydroxylation (AD) of primary allylic halides is described. Enantiomeric excesses range from 40 to 98%. Subsequent base treatment gives epoxy alcohols in high yields. This strategy is further illustrated by the synthesis of (-)-diepoxybutane, an important C-4-chiral building block.
• Asymmetric dihydroxylation of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix reagents. Effects of 1-acyloxy functional groups on the asymmetric dihydroxylation
  作者：Tsutomu Yokomatsu、Takehiro Yamagishi、Tomoyuki Sada、Kenji Suemune、Shiroshi Shibuya

  DOI：10.1016/s0040-4020(97)10342-8

  日期：1998.1

  Asymmetric dihydroxylation (AD) of a racemic mixture of 1-acyloxy-2(E)-alkenylphosphonates with AD-mix-alpha or -beta reagents was examined. The kinetic rate of dihydroxylation was highly dependent upon the configuration of the 1-acyloxy functional group as well as the nature of substituents at the 3-position. ?he reaction of a racemic mixture of diethyl (E)-3-phenyl-1-acetyloxy-2-propenylphosphonate with an AD-mix-beta reagent preferentially dihydroxylated the R-enantiomer to leave an unreacted S-enantiomer of high enantiomeric purity. Double diastereoselection of the resolved diethyl 3-phenyl-1-acetyloxy-2(E)-propenylphosphonate in dihydroxylation was also examined. (C) 1997 Elsevier Science Ltd. All rights reserved.