(E)-ethyl 3-((2R,3R)-3-(benzyloxymethyl)oxiran-2-yl)acrylate | 136880-99-4

• 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: (E)-ethyl 3-((2R,3R)-3-(benzyloxymethyl)oxiran-2-yl)acrylate
• 英文别名: ethyl trans-6-benzyloxy-4,5-epoxy-2(E)-hexenoate；ethyl 6-(benzyloxy)-4,5-trans-epoxy acrylate；ethyl (E)-3-[(2R,3R)-3-(phenylmethoxymethyl)oxiran-2-yl]prop-2-enoate
• CAS: 136880-99-4
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: HLTOFBRUWPKEFW-SJXIGLKTSA-N

物化性质

• 沸点：
  382.8±27.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 3-((2R,3R)-3-(benzyloxymethyl)oxiran-2-yl)acrylate 在 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 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：

  <2R-(2β,3α)>-3-<(phenylmethoxy)methyl>oxiranemethanol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 (E)-ethyl 3-((2R,3R)-3-(benzyloxymethyl)oxiran-2-yl)acrylate
  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

文献信息

• Palladium-Catalyzed Stereospecific Substitution of α,β-Unsaturated γ,δ-Epoxy Esters by Alcohols with Double Inversion of Configuration: Synthesis of 4-Alkoxy-5-hydroxy-2-pentenoates
  作者：Xiao-Qiang Yu、Fumihiko Yoshimura、Fumito Ito、Minoru Sasaki、Atsushi Hirai、Keiji Tanino、Masaaki Miyashita

  DOI：10.1002/anie.200703889

  日期：2008.1.11
• Stereospecific methylation of .gamma.,.delta.-epoxy acrylates by trimethylaluminum: a method for the iterative construction of polypropionate chains
  作者：Masaaki Miyashita、Masahide Hoshino、Akira Yoshikoshi

  DOI：10.1021/jo00023a001

  日期：1991.11

  A new and potentially useful method for the synthesis of polypropionates via the regio- and stereo-specific methylation of gamma,delta-epoxy acrylates by (CH3)3Al has been developed.
• Diastereoselective synthesis of the C29–C41 fragment of karlotoxin 2
  作者：D. Srinivas Reddy、Janardhan Gaddam、Nagaraju Devunuri、Debendra K. Mohapatra

  DOI：10.1016/j.tetlet.2015.05.051

  日期：2015.7

  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.