5-benzyloxy-2(Z)-pentenoic acid methyl ester | 169900-77-0

• 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: 5-benzyloxy-2(Z)-pentenoic acid methyl ester
• 英文别名: (Z)-methyl 5-(benzyloxy)-2-pentenoate；methyl 5-benzyloxy-2-(Z)-pentenoate；methyl (Z)-5-phenylmethoxypent-2-enoate
• CAS: 169900-77-0
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: RVALDTQCCVGPIC-UITAMQMPSA-N

物化性质

• 沸点：
  314.7±35.0 °C(predicted)
• 密度：
  1.057±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

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：

  5-benzyloxy-2(Z)-pentenoic acid methyl ester 在 lithium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以99%的产率得到5-benzyloxy-2-(Z)-pentenoic acid
  参考文献：
  名称：

  恶唑烷酮α-氟酰胺手性结构单元在氟化不对称合成2-脱氧-2-氟戊糖中的应用

  摘要：

  Z -α，β-不饱和酰亚胺（+）- 9的二烯酸锂与N-氟苯磺酰亚胺（NFSi）的去共轭亲电氟化得到E -β，γ-不饱和α-氟酰亚胺（+）- 10作为单一非对映异构体。二羟基化分别形成2-氟-2-脱氧-γ-木糖基内酯和-Lyxonic内酯12a和12b。内酯的还原和脱保护得到2-脱氧-2-氟-木糖基-吡喃糖（15）和2-脱氧-2-氟-木糖基-1-吡喃糖（17）。

  DOI：

  10.1016/s0040-4020(00)00444-0
• 作为产物：
  描述：

  3-苄氧基-1-丙醇 在 草酰氯 、 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 5-benzyloxy-2(Z)-pentenoic acid methyl ester
  参考文献：
  名称：

  2-脱氧-2-氟-γ-醛内酯的不对称合成及其向2-脱氧-2-氟戊糖的转化

  摘要：

  通过α，β-不饱和手性酰亚胺5的非对映选择性氟化，然后二羟基化，制备2-氟-2-脱氧-γ-二甲苯基和-二甲苯基内酯7a和7b。通过还原和脱保护，将内酯7a和7b转化为2-脱氧-2-氟-木糖基-吡喃糖（1）和2-脱氧-2-氟-木糖基-吡喃糖（2）。

  DOI：

  10.1016/0040-4039(96)00825-8

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。
• Asymmetric synthesis of 2-deoxy-2-fluoro-γ-aldonolactones and their conversion to 2-deoxy-2-fluoropentoses
  作者：Franklin A. Davis、Hongyan Qi

  DOI：10.1016/0040-4039(96)00825-8

  日期：1996.6

  2-Fluoro-2-deoxy-γ-xylonic and -lyxonic lactones, 7a and 7b, were prepared via the diastereoselective fluorination of the α,β-unsaturated chiral imide 5 followed by dihydroxylation. Lactones 7a and 7b were converted to 2-deoxy-2-fluoro-xylo-d-pyranose (1) and 2-deoxy-2-fluoro-lyxo-l-pyranose (2) by reduction and deprotection.

  通过α，β-不饱和手性酰亚胺5的非对映选择性氟化，然后二羟基化，制备2-氟-2-脱氧-γ-二甲苯基和-二甲苯基内酯7a和7b。通过还原和脱保护，将内酯7a和7b转化为2-脱氧-2-氟-木糖基-吡喃糖（1）和2-脱氧-2-氟-木糖基-吡喃糖（2）。
• 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.
• Application of Oxazolidinone α-Fluoro Amide Chiral Building Blocks in the Asymmetric Synthesis of Fluorinated Carbohydrates: 2-Deoxy-2-fluoropentoses
  作者：Franklin A Davis、Hongyan Qi、Gajendran Sundarababu

  DOI：10.1016/s0040-4020(00)00444-0

  日期：2000.7

  Deconjugative electrophilic fluorination of the lithium dienolate of Z-α,β-unsaturated imide (+)-9 with N-fluorobenzenesulfonimide (NFSi) afforded the E-β,γ-unsaturated α-fluoro imide (+)-10 as a single diastereoisomer. Dihydroxylation resulted in the formation of 2-fluoro-2-deoxy-γ-xylonic and -lyxonic lactones, 12a and 12b, respectively. Reduction and deprotection of the lactones afforded 2-deox

  Z -α，β-不饱和酰亚胺（+）- 9的二烯酸锂与N-氟苯磺酰亚胺（NFSi）的去共轭亲电氟化得到E -β，γ-不饱和α-氟酰亚胺（+）- 10作为单一非对映异构体。二羟基化分别形成2-氟-2-脱氧-γ-木糖基内酯和-Lyxonic内酯12a和12b。内酯的还原和脱保护得到2-脱氧-2-氟-木糖基-吡喃糖（15）和2-脱氧-2-氟-木糖基-1-吡喃糖（17）。