<2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranecarboxaldehyde | 114925-54-1

• 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: <2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranecarboxaldehyde
• 英文别名: (2S,3R)-3-benzyloxymethyloxirane-2-carbaldehyde；(2R,3S)-4-(Benzyloxy)-2,3-epoxybutanal；(2R-(2β,3α))-3-[(phenylmethoxy)methyl]oxiranecarboxaldehyde；(2S,3R)-3-(phenylmethoxymethyl)oxirane-2-carbaldehyde
• CAS: 114925-54-1
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: AOHLUAAULDSDPB-GHMZBOCLSA-N

物化性质

• 沸点：
  314.0±27.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranecarboxaldehyde 在 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 6.0h， 生成 (4S,5R,E)-4,6-bis(benzyloxy)hex-2-ene-1,5-diol
  参考文献：
  名称：

  Diastereoselective synthesis of the C29–C41 fragment of karlotoxin 2

  摘要：

  A highly diastereoselective synthesis of the C29-C41 fragment of karlotoxin 2 (KmTx2) is described by employing regio-selective epoxide opening, our own developed domino isomerization followed by C-O and C-C bond formation reaction and chelation-controlled Grignard reaction as key steps. The synthesis involves installation of seven stereocenters present in the C29-C41 fragment of karlotoxin 2. (c) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.051
• 作为产物：
  描述：

  4-benzyloxybut-2-enal 在 2-[bis(3,5-(trifluoromethyl)phenyl)(trimethylsilyloxy)methyl]pyrrolidine 、 双氧水 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 <2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranecarboxaldehyde
  参考文献：
  名称：

  An Organocatalytic Approach to 2-Hydroxyalkyl- and 2-Aminoalkyl Furanes

  摘要：

  The first enantioselective methodology for the synthesis of electron-poor 2-hydroxyalkyl- and 2-aminoalkyl furanes is demonstrated in this study. It utilizes a highly stereoselective organocatalytic one-pot reaction cascade: epoxidation or aziridination of alpha,beta-unsaturated aldehydes followed by Feist-Benary reaction of various 1,3-dicarbonyl compounds to give the target furanes. This efficient multibond forming reaction cascade benefits from low catalyst loadings and readily available starting materials. Furthermore, the possibility to interrupt the reaction sequence at the stage of the corresponding optically active 2-hydroxyalkyl- and 2-aminoalkyl 2,3-dihydrofuranes with three stereogenic centers is also presented. Finally, models which account for the formation of the optically active 2,3-dihydrofuranes are proposed.

  DOI：

  10.1021/ja108247t

文献信息

• Asymmetric Organocatalytic Epoxidation of α,β-Unsaturated Aldehydes with Hydrogen Peroxide
  作者：Mauro Marigo、Johan Franzén、Thomas B. Poulsen、Wei Zhuang、Karl Anker Jørgensen

  DOI：10.1021/ja051808s

  日期：2005.5.1

  The first asymmetric organocatalytic epoxidation of α,β-unsaturated aldehydes is presented. A chiral bisaryl−silyl-protected pyrrolidine acts as a very selective epoxidation organocatalyst using simple oxidation agents, such as hydrogen peroxide and tert-butyl hydroperoxide. The asymmetric epoxidation reactions proceed under environmental friendly reaction condition in, for example, water mixtures

  介绍了 α,β-不饱和醛的第一个不对称有机催化环氧化反应。手性双芳基-甲硅烷基保护的吡咯烷使用简单的氧化剂（如过氧化氢和叔丁基过氧化氢）作为一种非常有选择性的环氧化有机催化剂。不对称环氧化反应在环境友好的反应条件下进行，例如，在醇的水混合物中，反应的范围通过以高产率和对映选择性 > 94% ee 形成光学活性的 α,β-环氧醛来证明。此外，还介绍了通过柠檬醛的不对称环氧化从螨虫直接合成性信息素。
• A Stereoselective Total Synthesis of Xyolide, a Natural Bioactive Nonenolide
  作者：Lingaiah Maram、Biswanath Das

  DOI：10.1002/hlca.201400291

  日期：2015.5

  A stereoselective total synthesis of xyolide, a naturally occurring bioactive nonenolide, has been accomplished. The acid fragment of the molecule has been prepared from D‐mannitol and the alcohol fragment from (2Z)‐but‐2‐ene‐1,4‐diol. The synthesis involves the coupling of these two fragments using the Yamaguchi esterification protocol, followed by intramolecular ring‐closing methathesis. The diastereoisomeric

  已经完成了自然存在的生物活性壬烯内酯二甲酸酯的立体选择性全合成。该分子的酸片段是由D-甘露醇制备的，而醇片段是由（2 Z）-丁-2-烯-1,4-二醇制备的。合成过程涉及使用Yamaguchi酯化方案将这两个片段偶联，然后进行分子内闭环置换。通过采用Mitsunobu酯化反应，非对映异构醇片段也已用于该合成中。
• Reddy, N. Salva; Lingaiah; Das, Biswanath, Indian Journal of Heterocyclic Chemistry, 2015, vol. 24, # 4, p. 389 - 394
  作者：Reddy, N. Salva、Lingaiah、Das, Biswanath

  DOI：——

  日期：——
• An enantioselective route to cis- and trans-2-(hydroxymethyl)-5-alkylpyrrolidines
  作者：Helena Pettersson-Fasth、Steven W. Riesinger、Jan E. Baeckvall

  DOI：10.1021/jo00124a021

  日期：1995.9

  A general method for the enantioselective preparation of 2,5-disubstituted pyrrolidines has been developed. A variety of cis- and trans-2-(hydroxymethyl)-5-alkylpyrrolidin were synthesized using 1-(benzyloxy)-5-(p-toluenesulfonamido)-3-alken-2-ol as common intermediates.
• Total synthesis of amphoteronolide B and amphotericin B. 1. Strategy and stereocontrolled construction of key building blocks
  作者：Kyriacos C. Nicolaou、R. A. Daines、J. Uenishi、W. S. Li、D. P. Papahatjis、T. K. Chakraborty

  DOI：10.1021/ja00222a028

  日期：1988.7