(E)-3-benzyloxypropenoyl chloride | 154581-21-2

• 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)-3-benzyloxypropenoyl chloride
• 英文别名: (E)-3-benzyloxyacryloyl chloride；(E)-3-benzyloxyacrylic acid chloride；(2E)-3-(benzyloxy)acryloyl chloride；(E)-3-phenylmethoxyprop-2-enoyl chloride
• CAS: 154581-21-2
• 化学式: C₁₀H₉ClO₂
• 分子量: 196.633
• InChiKey: SEAOGZNQISMZAS-VOTSOKGWSA-N

物化性质

• 沸点：
  307.8±35.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-benzyloxypropenoyl chloride 在 甲基溴化镁 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 73.5h， 生成 (3R,4S)-4-benzyloxy-tetrahydrothiophene-3-carboxylic (1S)-camphorsultam amide
  参考文献：
  名称：

  Enantiomerically Pure trans-3,4-Disubstituted Tetrahydrothiophenes from Diastereoselective Thiocarbonyl Ylide Addition to Chiral α,β-Unsaturated Amides

  摘要：

  [GRAPHICS]Asymmetric 1,3-dipolar cycloadditions of a sulfur-containing 1,3-dipole and alpha,beta-unsaturated camphorsultam amides as dipolarophiles are described. The cycloaddition products, trans-3,4-disubstituted tetrahydrothiophenes, were obtained in high diastereomeric ratios (up to 90:10) and in high yields. Chromatographic removal of the minor diastereomer followed by cleavage of the chiral auxiliary furnished either the enantiomerically pure corresponding alcohol or carboxylic acid.

  DOI：

  10.1021/ol9910565
• 作为产物：
  描述：

  methyl (E)-β-benzyloxyacrylate 在 sodium hydroxide 、 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 生成 (E)-3-benzyloxypropenoyl chloride
  参考文献：
  名称：

  The samarium(II)-mediated intermolecular couplings of ketones and β-alkoxyacrylates: a short asymmetric synthesis of an antifungal γ-butyrolactone

  摘要：

  The samarium(II) iodide-mediated coupling of ketones with beta-alkoxyacrylatcs gives beta-hydroxy-gamma-butyrolactones in moderate yield. The process has been applied to the asymmetric synthesis of an antifungal, gamma-butyrolactone natural product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.027

文献信息

• Improved Synthesis of (<i>E</i>)-3-Alkoxy- and (<i>E</i>)-3-Phenoxyacryloyl Chlorides
  作者：L. F. Tietze、C. Schneider、M. Pretor

  DOI：10.1055/s-1993-26002

  日期：——

  A one-step preparation of (E)-3-alkoxy- and (E)-3-phenoxyacryloyl chlorides by reaction of vinyl ethers and oxalyl chloride with subsequent decarbonylation is presented.

  通过乙烯醚和草酰氯反应后随之进行脱羰，提出了一种一步法制备(E)-3-烷氧基和(E)-3-苯氧基丙烯酰氯的方法。
• Process for the preparation of substituted pyrrolidine derivatives and intermediates
  申请人：Chand Pooran

  公开号：US20060128789A1

  公开（公告）日：2006-06-15

  Two syntheses are provided; one for the preparation of (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol, and other for the preparation of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is prepared using the achiral ylide prepared from benzylamine instead of phenethylamine (Scheme 3) which provides a crystalline intermediate. The synthesis of (3S,4R)-4-(hydroxymethyl)pyrrolidin-3-ol is achieved from (S)-diethylmalate as described in Scheme 4. A process for preparing camphor sultam is also provided.

  提供两种合成方法；一种是制备(3R,4R)-4-(羟甲基)吡咯烷-3-醇，另一种是制备(3S,4R)-4-(羟甲基)吡咯烷-3-醇。使用从苄胺而非苯乙胺制备的无手性叶烯制备(3R,4R)-4-(羟甲基)吡咯烷-3-醇（方案3），该方法提供了结晶中间体。根据方案4的描述，可以从(S)-乙二酸二乙酯合成(3S,4R)-4-(羟甲基)吡咯烷-3-醇。还提供了一种制备樟脑磺酰胺的方法。
• A Practical Large-Scale Synthesis of (3<i>R</i>,4<i>R</i>)-4-(Hydroxymethyl)pyrrolidin-3-ol via Asymmetric 1,3-Dipolar Cycloaddition
  作者：Pravin L. Kotian、Tsu-Hsing Lin、Yahya El-Kattan、Pooran Chand

  DOI：10.1021/op049768k

  日期：2005.3.1

  (3R,4R)-4-(Hydroxymethyl)pyrrolidin-3-ol (1), which is a useful intermediate for the synthesis of various bioactive molecules, has been synthesized in 51% overall yield by 1,3-dipolar cycloaddition reaction from the dipolarophile, (E)-3-benzyloxypropenoyl-(2‘S)-bornane-10,2-sultam (5), and the achiral ylide precursor, N-(benzyl)-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine (6), without using chromatography

  （3 R，4 R）-4-（羟甲基）吡咯烷-3-醇（1）是合成各种生物活性分子的有用中间体，已通过1,3-偶极环加成法以51％的总产率合成从亲偶极反应，（ê）-3- benzyloxypropenoyl-（2'小号）-bornane-10,2-磺内酰胺（5），和非手性前体叶立德，ñ - （苄基） - ñ - （甲氧基甲基） - ñ - （三甲基甲硅烷基甲基）胺（6），无需使用色谱法，随后用LAH还原并进行催化氢化。非对映异构体7和8经结晶分离，并开发出有效的方法用于随后的反应，得到1。
• US7230119B2
  申请人：——

  公开号：US7230119B2

  公开（公告）日：2007-06-12
• The samarium(II)-mediated intermolecular couplings of ketones and β-alkoxyacrylates: a short asymmetric synthesis of an antifungal γ-butyrolactone
  作者：Nessan J. Kerrigan、Tejas Upadhyay、David J. Procter

  DOI：10.1016/j.tetlet.2004.10.027

  日期：2004.11

  The samarium(II) iodide-mediated coupling of ketones with beta-alkoxyacrylatcs gives beta-hydroxy-gamma-butyrolactones in moderate yield. The process has been applied to the asymmetric synthesis of an antifungal, gamma-butyrolactone natural product. (C) 2004 Elsevier Ltd. All rights reserved.

表征谱图