syn-1-Phenyl-2,3-epoxy-1-propanol | 33143-44-1

• 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: syn-1-Phenyl-2,3-epoxy-1-propanol
• 英文别名: (S)-[(2S)-oxiran-2-yl]-phenylmethanol
• CAS: 33143-44-1；91420-78-9；107643-29-8；107643-32-3；127913-26-2；127913-27-3；146388-55-8
• 化学式: C₉H₁₀O₂
• 分子量: 150.177
• InChiKey: QHUCJYPNJYZEOQ-IUCAKERBSA-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：

  syn-1-Phenyl-2,3-epoxy-1-propanol 在 lithium aluminium tetrahydride 作用下， 生成 (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：

  (Z)-1-phenyl-3-(trimethylsilyl)prop-2-en-1-ol 在 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 、 cesium fluoride 作用下， 以 二甲基亚砜 为溶剂， 生成 syn-1-Phenyl-2,3-epoxy-1-propanol
  参考文献：
  名称：

  Stereoselective introduction of chiral centres in acylic precursors: a probe into the transition state for V5+-catalyzed t-butylhydroperoxide (TBHP) epoxidation of acyclic allylic alcohols and its synthetic implications.

  摘要：

  DOI：

  10.1016/s0040-4039(00)85899-2

文献信息

• Novel synthesis of syn-α,β-epoxy alcohols by diastereoselective carbonyl reduction of α,β-epoxy ketones
  作者：Takayo Kawakami、Ikuya Shibata、Akio Baba、Haruo Matsuda、Noboru Sonoda

  DOI：10.1016/s0040-4039(00)78454-1

  日期：1994.11

  A novel tin hydride reagent, Bu3SnH-Bu4NCN, reduced α,β-epoxy ketones to the corresponding syn-α,β-epoxy alcohols in high diastereoselectivities.

  一种新型的氢化锡试剂Bu 3 SnH-Bu 4 NCN，可在高非对映选择性下将α，β-环氧酮还原为相应的顺式-α，β-环氧醇。
• Enantio- and diastereocontrolled conversion of chiral epoxides to trans-cyclopropane carboxylates: application to the synthesis of cascarillic acid, grenadamide and <scp>l</scp>-(−)-CCG-II
  作者：Pradeep Kumar、Abhishek Dubey、Anand Harbindu

  DOI：10.1039/c2ob25622c

  日期：——

  An efficient high yielding improved method for the enantio- and diastereoselective cyclopropanation of chiral epoxides using triethylphosphonoacetate and base (Wadsworth–Emmons cyclopropanation) is reported. The utility of this protocol is illustrated by concise and practical synthesis of cascarillic acid, grenadamide and L-(−)-CCG-II, a cyclopropane containing natural products.

  报道了一种使用三乙基膦酰基乙酸酯和碱对手性环氧化合物进行对映和非对映选择性环丙烷化的高效高产改良方法（Wadsworth-Emmons环丙烷化）。该协议的实用性通过简明而实用的合成卡斯卡利酸来说明，格林纳丁胺 L-（-）-CCG-II，一种含环丙烷的天然产物。
• Divergent stereoselectivity in the reduction of α,β-Epoxy ketones using hydridosilicates
  作者：Makoto Hojo、Atsuko Fujii、Chikara Murakami、Hidenori Aihara、Akira Hosomi

  DOI：10.1016/0040-4039(94)02255-a

  日期：1995.1

  α,β-Epoxy ketones are reduced by trimethoxysilane in the presence of a catalytic amount of lithium methoxide to yield the corresponding alcohols. This reaction system reveals divergent selectivity depending on the solvent; both anti-selectivity and syn-selectivity are observed iin less polar Et2O and in polar HMPA, respectively.

  在催化量的甲醇锂存在下，通过三甲氧基硅烷还原α，β-环氧酮，得到相应的醇。该反应体系根据溶剂显示出不同的选择性。在较低极性的Et 2 O中和在极性HMPA中分别观察到抗选择性和顺选择性。
• <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。
• Organocatalyzed Protecting-Group-Free Total Synthesis of (<i>S,S</i>)- and (<i>S,R</i>)-Reboxetine, an Antidepressant Drug
  作者：Ajay Sharma、Satyendra Kumar Pandey

  DOI：10.1021/acs.joc.2c00886

  日期：2022.8.5

  protecting-group-free synthetic approach to the stereoisomers of the antidepressant drug reboxetine and its implementation toward the asymmetric synthesis of (S,S)-reboxetine and (S,R)-reboxetine from commercially available trans-cinnamaldehyde are described. The synthesis features organocatalytic Jørgensen asymmetric epoxidation, epoxide migration, and Mitsunobu inversion as key steps.

  一种高效、简单、简洁的有机催化无保护基团合成抗抑郁药瑞波西汀立体异构体的方法及其对市售反式不对称合成 ( S,S )-瑞波西汀和 ( S,R )-瑞波西汀的实施描述了-肉桂醛。该合成以有机催化 Jørgensen 不对称环氧化、环氧化物迁移和 Mitsunobu 反转为关键步骤。