(2S,3R)-(-)-5-oxo-2-pentyltetrahydrofuran-3-carboxylic acid | 142188-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (2S,3R)-(-)-5-oxo-2-pentyltetrahydrofuran-3-carboxylic acid
• 英文别名: (2S,3R)-5-oxo-2-pentyloxolane-3-carboxylic acid
• CAS: 142188-51-0
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: UEECRARBSXJSKY-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3R)-(-)-5-oxo-2-pentyltetrahydrofuran-3-carboxylic acid 在 吖啶 、 叔丁基硫醇 作用下， 以 苯 为溶剂， 反应 3.0h， 以57%的产率得到(S)-二羟基-5-戊基-2(3H)-呋喃酮
  参考文献：
  名称：

  Novel, enantioselective lactone construction. First synthesis of methylenolactocin, antitumor antibiotic from Penicillium sp

  摘要：

  The first synthesis of (-)-methylenolactocin, which illustrates a novel approach to enantiopure gamma-butyrolactones and serves to confirm the structure and establish the absolute stereochemistry of the natural product, is reported.

  DOI：

  10.1021/jo00043a003
• 作为产物：
  描述：

  trans-(4R,5S)-5-pentyl-2-butoxytetrahydrofuran-4-carbaldehyde 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.08h， 以90%的产率得到(2S,3R)-(-)-5-oxo-2-pentyltetrahydrofuran-3-carboxylic acid
  参考文献：
  名称：

  Stereoselective Synthesis of Heterocyclic Zinc Reagents via a Nickel-Catalyzed Radical Cyclization

  摘要：

  Unsaturated iodo or bromo acetals of type 2 undergo a smooth cyclization mediated by diethylzinc (2 equiv) and Ni(acac)(2) as catalyst (2-5 mol %). These cyclizations proceed via a radical mechanism affording a (tetrahydrofuranylmethyl)zinc halide of type 1, which can be reacted with various electrophiles after a transmetalation with CuCN . 2LiCl. High stereoselectivities are usually observed in the ring closures, especially if monocyclic cyclization precursors are used. In these cases, bicyclic products of the endo-configuration are obtained with over 94% diastereoselectivity. The synthetic method has been extended to the preparation of a nitrogen heterocycle and over 98% pure trans-4,5-disubstituted gamma-butyrolactones. A short enantioselective synthesis of (-)-methylenolactocine (3) using the radical cyclization and a novel oxidation of alpha-silyl zinc peroxide as a key step is also described.

  DOI：

  10.1021/jo960617s

文献信息

• An enantioselective synthesis of 3,4-disubstituted butyrolactones
  作者：Toshio Honda、Nobuaki Kimura

  DOI：10.1039/c39940000077

  日期：——

  An enantioselective synthesis of γ-butyrolactones including a formal synthesis of (–)-methylenolactocin 1 is achieved by employing an enantioselective deprotonation of 3-phenylcyclobutanone as a key step.

  通过采用3-苯基环丁酮的手性选择性去质子化作为关键步骤，成功实现了γ-丁内酯的对映选择性合成，包括(–)-美克莱诺内酯1的形式合成。
• Enantioselective Synthesis of Paraconic Acids
  作者：Rakeshwar B. Chhor、Bernd Nosse、Sebastian Sörgel、Claudius Böhm、Michael Seitz、Oliver Reiser

  DOI：10.1002/chem.200390019

  日期：2003.1.3

  development of a new method for the enantioselective synthesis of disubstituted gamma-butyrolactones is reported. Based on this strategy, the total synthesis of three paraconic acids, that is (-)-roccellaric acid, (-)-nephrosteranic acid and (-)-protopraesorediosic acid, and the formal total synthesis of (-)-methylenolactocin and (-)-protolichesterinic acid is described, which are important because of their

  据报道，开发了一种对映选择性合成双取代的γ-丁内酯的新方法。在此策略的基础上，可以合成（-）-二十二碳六烯酸，（-）-肾甾酸和（-）-戊二酸二十二碳三酸，以及（-）-甲基烯醇内酯和（- ）-原脂白蛋白酸，其具有重要的抗生素和抗肿瘤特性，因此非常重要。合成的关键步骤是铜（I）催化的呋喃的不对称环丙烷化，高度非对映选择性的樱井烯丙基化，路易斯酸或路易斯碱催化的逆向醇/内酯化级联反应，以及钌（II）催化的分子间交叉易位反应。
• Concise syntheses of (+)- and (−)-methylenolactocins and phaseolinic acids
  作者：Saumen Hajra、Ananta Karmakar、Aswini Kumar Giri、Sunit Hazra

  DOI：10.1016/j.tetlet.2008.04.001

  日期：2008.5

  (+)- and (-)-Methylenolactocins and phaseolinic acids are synthesized in four steps via asymmetric syn- and anti-aldol reactions of chiral N- succinyl-2-oxazolidinones using the same set of reagents. (C) 2008 Elsevier Ltd. All rights reserved.

  (+)-和(-)-甲基烯醇和相豆甾酸通过四步合成，采用手性N-琥珀酰-2-氧杂环丁-3-酮的不对称顺式和反式缩醛反应，使用相同的试剂组。版权属于2008 Elsevier Ltd.，所有权利保留。
• Stereodivergent Synthesis of Chiral Paraconic Acids via Dynamic Kinetic Resolution of 3-Acylsuccinimides
  作者：Abhijeet M. Sarkale、Vidyasagar Maurya、Sachin Giri、Chandrakumar Appayee

  DOI：10.1021/acs.orglett.9b01445

  日期：2019.6.7

  N-heterocyclic carbene (NHC) catalysis of maleimides with alkyl aldehydes is established for the synthesis of 3-acylsuccinimides. The first dynamic kinetic resolution of 3-acylsuccinimides is accomplished through asymmetric transfer hydrogenation. These two catalytic methodologies are utilized for the synthesis of each enantiomer of trans-paraconic acids in three steps and cis-paraconic acids in four steps

  建立具有烷基醛的马来酰亚胺的直接N-杂环卡宾（NHC）催化，以合成3-酰基琥珀酰亚胺。3-酰基琥珀酰亚胺的第一动态动力学拆分是通过不对称转移氢化实现的。这两种催化方法被用于以三个步骤合成反式-对conconic酸的每个对映异构体和以四个步骤来合成顺式-对conconconic酸，具有良好的收率和高的立体选择性。这种立体发散的合成方法可用于合成七种生物活性对锥酸天然产物。
• Photochemical C-C Bond Formation between Alcohols and Olefins by an Environmentally Benign Radical Reaction
  作者：Akihiko Ouchi、Chuanxiang Liu、Masayuki Kaneda、Takeshi Hyugano

  DOI：10.1002/ejoc.201300115

  日期：2013.6

  A radical C–C bond formation between olefins and alcohols proceeded efficiently by simple light irradiation at room temperature. The reaction proceeded in the presence of commercially available tBuOOtBu without using the harmful elements and/or compounds that have an unpleasant smell that are often used in conventional radical reactions. In addition, the reaction did not require photosensitizers or

  在室温下，通过简单的光照射，烯烃和醇之间的自由基 C-C 键形成有效地进行。该反应在市售的 tBuOOtBu 存在下进行，不使用常规自由基反应中经常使用的有害元素和/或具有难闻气味的化合物。此外，该反应不需要光敏剂或光催化剂，这消除了反应后敏化剂的耗时分离，或之前程序中报道的光催化剂的合成。