(E)-methyl 5-(benzyloxy)-2-pentenoate | 128217-53-8

• 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: (E)-methyl 5-(benzyloxy)-2-pentenoate
• 英文别名: 2-Pentenoic acid, 5-(phenylmethoxy)-, methyl ester, (2E)-；methyl (E)-5-phenylmethoxypent-2-enoate
• CAS: 128217-53-8
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: RVALDTQCCVGPIC-WEVVVXLNSA-N

物化性质

• 沸点：
  140 °C(Press: 0.9 Torr)
• 密度：
  1.057±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 5-(benzyloxy)-2-pentenoate 在 sodium hydroxide 、 氯化二乙基铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (S)-4-Benzyl-3-[(1S,2R,3R,4R)-3-(2-benzyloxy-ethyl)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-oxazolidin-2-one
  参考文献：
  名称：

  Asymmetric Diels-Alder reactions with .gamma.-functionalized .alpha.,.beta.-unsaturated chiral N-acyloxazolidinones: synthesis of (+)-S-145

  摘要：

  DOI：

  10.1021/jo00304a019
• 作为产物：
  描述：

  3-苄氧基-1-丙醇 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 (E)-methyl 5-(benzyloxy)-2-pentenoate
  参考文献：
  名称：

  Dihydrocorynanthenol、Protoemetinol、Protoemetine、3-epi-Protoemetinol 和 Emetine 的简明全合成

  摘要：

  公开了一种通过一锅三组分级联反应方法对 secologanine 色胺和多巴胺生物碱进行简明不对称组装的方法。这体现在快速...

  DOI：

  10.1002/ejoc.201101296

文献信息

• Syntheses of α,β-Unsaturated Carbonyl Compounds from the Reactions of Monosubstituted Ozonides with Stable Phosphonium Ylides
  作者：Yung-Son Hon、Ling Lu、Rong-Chi Chang、Sheng-Wun Lin、Pei-Pei Sun、Chia-Fu Lee

  DOI：10.1016/s0040-4020(00)00903-0

  日期：2000.11

  Ozonides derived from terminal alkenes reacted with 1.3 mol equiv. of stable phosphonium ylides to give (E)-α,β-unsaturated carbonyl compounds in good to excellent yields. No reducing agent is needed in the reaction. However, alkoxyalkyl-substituted ozonides afforded a mixture of (Z)- and (E)-α,β-unsaturated carbonyl compounds under similar condition. The E/Z isomeric ratio is affected by the position

  衍生自末端烯烃的臭氧与1.3摩尔当量反应。稳定的叶立德phospho以良好至极好的收率得到（E）-α，β-不饱和羰基化合物。反应中不需要还原剂。然而，烷氧基烷基取代的臭氧化物在相似条件下得到（Z）-和（E）-α，β-不饱和羰基化合物的混合物。所述ë / ž异构体比率是由杂原子中的臭氧化物的取代基的位置的影响。将讨论该反应的可能机理。
• Total synthesis of the ionophore antibiotic CP-61,405 (routiennocin)
  作者：David Díez-Martin、Nikesh R. Kotecha、Steven V. Ley、Sergio Mantegani、J.Carlos Menéndez、Helen M. Organ、Andrew D. White、Bernard J. Banks

  DOI：10.1016/s0040-4020(01)80467-1

  日期：1992.1

  The total synthesis of the spiroketal ionophore antibiotic routiennocin 1 (CP-61,405) employing π-allyltricarbonyl iron lactone complexes is described. These complexes were used as precursors for the preparation of substituted 2-phenylsulphonyl pyrans which, in turn, were coupled with iodoacetonides to afford spiroketals. Elaboration of the spiroketals by tetra-n-propylammonium perruthenate (TPAP)

  描述了使用π-烯丙基三羰基铁内酯配合物的螺酮离子载体抗生素routiennocin 1（CP-61,405）的全合成。这些络合物用作制备取代的2-苯基磺酰基吡喃的前体，然后将其与碘代丙酮化物偶联以提供螺缩酮。通过四正丙基过钌酸铵（TPAP）氧化并与2-lithio-1- [β-（三甲基甲硅烷基）乙氧基甲基]吡咯偶联，然后进一步氧化，脱保护，氧化和形成苯并恶唑，来合成螺环酮。苯并恶唑形成所需的氨基苯酚片段的制备涉及使用苯硒酸酐和六甲基二硅氮烷进行新颖的胺化步骤，然后还原二碘化sa。
• Enantioselective hydrolysis of dialkyl 3-monosubstituted glutarates with pig liver esterase: Structure-optical purity relationships
  作者：Masahisa Nakada、Susumu Kobayashi、Masaji Ohno、Shigeo Iwasaki、Shigenobu Okuda

  DOI：10.1016/s0040-4039(00)80391-3

  日期：1988.1

  Dialkyl 3-monosubstituted glutarates are subjected to hydrolysis with pig liver esterase to afford the corresponding chiral half-esters. Synthetically useful half-esters of higher optical purity are obtained from the prochiral substrates of more hydrophobic nature.

  用猪肝酯酶水解3-单取代的戊二酸二烷基酯，得到相应的手性半酯。从具有更疏水性质的前手性底物获得了更高光学纯度的合成上有用的半酯。
• Synthesis of the ABCD and ABCDE ring systems of azaspiracid-1
  作者：Xiao-Ti Zhou、Rich G. Carter

  DOI：10.1039/b410092a

  日期：——

  The efficient syntheses of the ABCD ring system of the originally proposed structure of azaspiracid-1 and the ABCDE ring system of the revised structure of azaspiracid-1 containing the correct stereochemistry at C6, C10, C13, C14, C16, C17, C19, C21, C22, C24 and C25 have been achieved.

  高效合成了最初提出的氮杂环氨酸-1 结构的 ABCD 环系统和修订后的氮杂环氨酸-1 结构的 ABCDE 环系统，其中包含正确的 C6、C10、C13、C14、C16、C17、C19、C21、C22、C24 和 C25 立体化学结构。
• A Simple Route to .alpha.-Substituted-.beta.-Amino Ester Precursors of Carbapenem Antibiotics
  作者：Patrick Perlmutter、Mark Tabone

  DOI：10.1021/jo00125a043

  日期：1995.10

  A three-step process is presented for the preparation of alpha-substituted-beta-amino esters which can serve as precursors to a key intermediate in carbapenem synthesis. The pivotal reaction in this sequence involves a highly diastereoselective conjugate addition reaction. Two series of alkenoates bearing a stereogenic substituent attached to C2 were prepared and their conjugate addition reactions with benzylamine studied under several different sets of conditions. Conjugate addition of benzylamine to alkenoates 7a and 7d, in methanol at room temperature, gave adducts 8a and Sd with virtually complete anti-diastereoselectivity. These two beta-amino esters bear the correct relative stereochemistry and side chain to serve as precursors for carbapenem antibiotic synthetic intermediates. The role of the allylic substituents of the alkenoates 7a-e in determining the stereochemical outcome of these additions is discussed. These conjugate additions were explored further by the preparation and conjugate addition reactions of the alpha,beta-disubstituted alkenoates 15a and 15b. It was found that the presence of a beta-substituent led to a dramatic reduction in yield although the same anti-diastereoselectivity was maintained. The relative stereochemistry of the adducts was established by examination of the relevant coupling constants in the H-1 NMR spectra of their tetrahydro-1,3-oxazine derivatives.