(R)-2-phenethyloxirane | 141036-66-0

• 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: (R)-2-phenethyloxirane
• 英文别名: (2R)-2-(2-Phenylethyl)oxirane
• CAS: 141036-66-0
• 化学式: C₁₀H₁₂O
• 分子量: 148.205
• InChiKey: JVGAGAVQROERFI-SNVBAGLBSA-N

物化性质

• 沸点：
  90-110 °C(Press: 7.0 Torr)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-phenethyloxirane 在 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 三氟化硼乙醚 作用下， 反应 21.17h， 生成 ethyl (3R,4R,5S)-4-acetamido-5-azido-3-[(3S)-1-phenylpentan-3-yl]oxycyclohexene-1-carboxylate
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Carbocyclic Influenza Neuraminidase Inhibitors

  摘要：

  A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized anti evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.

  DOI：

  10.1021/jm980162u
• 作为产物：
  描述：

  (2R)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (R)-2-phenethyloxirane
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Carbocyclic Influenza Neuraminidase Inhibitors

  摘要：

  A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized anti evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.

  DOI：

  10.1021/jm980162u

文献信息

• Manganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates
  作者：Hannah Shenouda、Erik J. Alexanian

  DOI：10.1021/acs.orglett.9b03706

  日期：2019.11.15

  The development of a stereospecific hydroxymethylation of alkyl tosylates using an inexpensive, first-row catalyst is described. The transformation proceeds under mild conditions with low pressure to deliver homologated alcohols as products. Chiral, nonracemic β-branched primary alcohols are obtained with high enantiospecificity from easily accessed secondary alkyl substrates. Simple modification of

  描述了使用便宜的第一行催化剂开发烷基甲苯磺酸酯的立体有针对性的羟甲基化。该转化在温和条件下以低压进行，以递送作为产物的同系醇。从容易获得的仲烷基底物上获得具有高对映体特异性的手性，非外消旋的β-支链伯醇。将反应体系的简单修改还允许访问α- ð 2醇。这些研究使用阴离子金属羰基催化，以从一氧化碳中获得具有挑战性的羟甲基阴离子的合成等价物。
• Enantioselective Synthesis of Cyclopropanone Equivalents and Application to the Formation of Chiral β‐Lactams
  作者：Christopher M. Poteat、Yujin Jang、Myunggi Jung、J. Drake Johnson、Rachel G. Williams、Vincent N. G. Lindsay

  DOI：10.1002/anie.202006786

  日期：2020.10.12

  derivatives have long been considered unsustainable synthetic intermediates because of their extreme strain and kinetic instability. Reported here is the enantioselective synthesis of 1‐sulfonylcyclopropanols, as stable yet powerful equivalents of the corresponding cyclopropanone derivatives, by α‐hydroxylation of sulfonylcyclopropanes using a bis(silyl) peroxide as the electrophilic oxygen source. This

  长期以来，环丙烷酮衍生物一直被认为是不可持续的合成中间体，因为它们的极限应变和动力学不稳定。此处报道的是通过使用双（甲硅烷基）过氧化物作为亲电子氧源通过磺酰基环丙烷的α-羟基化反应，以对映选择性的方式合成1-磺酰基环丙醇，它是相应环丙烷酮衍生物的稳定而功能强大的当量。这项工作是对映体丰富的环丙烷酮衍生物的第一个通用方法。磺酰基部分的电子和空间性质都可以用作碱不稳定的保护基，并赋予这些环丙烷酮前体结晶性，这对平衡相应环丙烷酮的速率具有至关重要的影响。
• Asymmetric epoxidation of alkenes and benzylic hydroxylation with P450tol monooxygenase from Rhodococcus coprophilus TC-2
  作者：Aitao Li、Shuke Wu、Joseph P. Adams、Radka Snajdrova、Zhi Li

  DOI：10.1039/c4cc03491k

  日期：——

  P450tol monooxygenase was discovered as a unique and highly enantioselective enzyme for asymmetric epoxidation of some terminal alkenes containing electron-withdrawing groups and benzylic hydroxylation of several ethylbenzenes giving the corresponding useful and valuable products, such as (R)-2- and 3-substituted styrene oxides, (S)-4-substituted styrene oxides, and (S)-benzylic alcohols, in high ee

  发现P450tol单加氧酶是一种独特的高对映选择性酶，用于某些含吸电子基团的末端烯烃的不对称环氧化和若干乙苯的苄基羟基化作用，从而提供相应的有用和有价值的产物，例如（R）-2-和3-取代的苯乙烯高ee的三价氧化物，（S）-4-取代的苯乙烯氧化物和（S）-苄基醇。
• Development of a robust immobilized organocatalyst for the redox-neutral mitsunobu reaction
  作者：Leijie Zhou、Stefania Perulli、Marco M. Mastandrea、Patricia Llanes、Junshan Lai、Miquel A. Pericàs

  DOI：10.1039/d1gc02819g

  日期：——

  polystyrene-supported version of the Denton catalyst for redox-neutral Mitsunobu reactions, (2-hydroxybenzyl)diphenylphosphine oxide, has been developed and used in catalytic inversion of enantiopure secondary alcohols (21 examples, up to 97% yield and 98% ee) with 2-nitrobenzoic and 2,4-dinitrobenzoic acids. The use in the reaction of alternative pronucleophiles has also been explored (8 successful and

  一种用于氧化还原-中性光信反应的丹顿催化剂的聚苯乙烯载体版本，（2-羟基苄基）二苯基氧化膦，已被开发并用于对映纯仲醇的催化转化（21 个例子，高达 97% 的产率和 98% ee）与 2-硝基苯甲酸和 2,4-二硝基苯甲酸。还探索了替代亲核试剂在反应中的使用（8 个成功的例子和 3 个不成功的例子）。该功能性树脂具有很高的可回收性（10 个循环，30 天运行），并且可以通过用丁胺进行简单处理来重新活化，并进一步延长其使用寿命。
• Stereoselective, Ag-Catalyzed Cyclizations To Access Polysubstituted Pyran Ring Systems: Synthesis of C₁–C₁₂ Subunit of Madeirolide A
  作者：Kazuhiro Watanabe、Jinming Li、Nagarathanam Veerasamy、Ankan Ghosh、Rich G. Carter

  DOI：10.1021/acs.orglett.6b00414

  日期：2016.4.15

  into the scope of a silver-catalyzed cyclization (AgCC) of propargyl benzoates for accessing pyran ring systems has been reported. The impact of the degree of substitution, nature of the substitution on the carbon backbone/benzoate moiety, and stereochemistry has been evaluated. The application of this methodology to the synthesis of the C1–C12 southern fragment of madeirolide A is disclosed.

  已经报道了对丙炔基苯甲酸酯的银催化环化（AgCC）以进入吡喃环系统的范围的探索。已经评估了取代度，取代性质对碳主链/苯甲酸酯部分和立体化学的影响。公开了该方法在合成马来酰内酯A的C 1 -C 12南部片段中的应用。