(S)-(+)-2-Phenyl-3-oxa-5-hexensaeure-ethylester | 134180-62-4

• 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: (S)-(+)-2-Phenyl-3-oxa-5-hexensaeure-ethylester
• 英文别名: ethyl (S)-(+)-2-allyloxy-2-phenylacetate；ethyl (2S)-2-phenyl-2-prop-2-enoxyacetate
• CAS: 134180-62-4
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: IRXLGPZMCKBWMW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：

  (S)-(+)-2-Phenyl-3-oxa-5-hexensaeure-ethylester 在 镍 二异丁基氢化铝 、 magnesium sulfate 作用下， 以 乙醚 、 正己烷 、 异丙醇 为溶剂， 反应 21.0h， 生成 (2S,3R,4R)-3-<(4-tert-Butylphenyl)amino>tetrahydro-4-(hydroxymethyl)-2-phenylfuran
  参考文献：
  名称：

  Aurich, Hans Guenther; Biesemeier, Frank; Boutahar, Mostafa, Chemische Berichte, 1991, vol. 124, # 10, p. 2329 - 2334

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,2-三氯乙酰胺烯丙酯 、 L-(+)-扁桃酸乙酯 在 三氟甲磺酸 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以4.46 mmol的产率得到(S)-(+)-2-Phenyl-3-oxa-5-hexensaeure-ethylester
  参考文献：
  名称：

  One-Pot Generation and Conversion of Trichloroacetimidates for the Racemization-Free Allylation and Benzylation of α-Hydroxyesters and the Enantiopure Synthesis of a Chiral Diglycole

  摘要：

  O-Allylations and O-benzylations of alpha -hydroxy esters (3a-3c) are performed without racemization. The reagents applied, O-allyl- and O-benzyltrichloroacetimidate (5a, 5b) are prepared and converted in a one-pot-procedure. After protection by benzylation (S)-(-)-ethyl lactate (3a) is converted by a sequence of carbonyl reduction, alcohol activation, ether formation, and deprotection to the optically active diglycole derivative 1a.

  DOI：

  10.1002/1521-3897(200009)342:7<654::aid-prac654>3.3.co;2-q

文献信息

• Intramolecular 1,3-Dipolar Cycloaddition of Transient Enantiomerically Pure Oxaalkenyl Nitrones
  作者：Hans Günter Aurich、Frank Biesemeier

  DOI：10.1055/s-1995-4060

  日期：1995.9

  A variety of enantiomerically pure α-hydroxy esters were converted into enantiomerically pure 3,7-dioxa-2-azabicyclo[3.3.0]octanes 7 by the following reaction sequence. Allylation of the hydroxy group was followed by reduction of the ester group. The resulting aldehyde was treated with an N-alkylhydroxylamine to give an oxaalkenyl nitrone 6 which underwent spontaneously an intramolecular 1,3-dipolar cycloaddition affording 7. Opening of the isoxazolidine ring of 7 by various reductive methods yielded the highly substituted tetrahydrofuran derivatives 11.

  多种手性纯的α-羟基酯通过以下反应序列转化为手性纯的3,7-二氧杂-2-氮杂双环[3.3.0]辛烷7。首先是羟基的烯丙基化，随后酯官能团被还原。生成的醛与N-烷基羟胺反应得到氧杂烯基硝酮6，该硝酮自发进行1,3-偶极环加成反应生成产物7。通过多种还原方法解开产物7中的异恶唑啉环，得到高度取代的四氢呋喃衍生物11。
• Stereoselective intramolecular cycloadditions of homochiral nitrilimines: synthesis of enantiopure (6S)-substituted-2,3,3a,4,5,6-hexahydro-furo[3,4-c]pyrazoles
  作者：Lara De Benassuti、Luisa Garanti、Giorgio Molteni

  DOI：10.1016/j.tetasy.2004.02.002

  日期：2004.4

  Starting from (S)-ethyl lactate and (S)-ethyl mandelate the homochiral hydrazonoyl chlorides 4b-d have been synthesised. Their base treatment promoted the in situ generation of the corresponding nitrilimines 5b-d, which gave the enantiopure title compounds with good overall yields and diastereoselectivities. (C) 2004 Elsevier Ltd. All rights reserved.