cis-2-methylene-3,4-diphenylbutano-4-lactone | 105400-43-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-2-methylene-3,4-diphenylbutano-4-lactone
• 英文别名: (4S,5R)-3-methylidene-4,5-diphenyloxolan-2-one
• CAS: 105400-43-9
• 化学式: C₁₇H₁₄O₂
• 分子量: 250.297
• InChiKey: VLJQNNIXUWORNH-CVEARBPZSA-N

物化性质

• 沸点：
  411.1±45.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  cis-2-methylene-3,4-diphenylbutano-4-lactone 以 乙醚 为溶剂， 反应 0.5h， 生成 (E)-but-2-enedioic acid;(3R,4S,5S)-3-(morpholin-4-ylmethyl)-4,5-diphenyloxolan-2-one
  参考文献：
  名称：

  Synthetic α-(aminomethyl)-γ-butyrolactones and their anti-pancreatic cancer activities

  摘要：

  Aminated alpha-methylene-c-butyrolactones, which are readily synthesized with facile control of the diastereoisomerism, provide an economical and commercially-viable alternative to the use of aminated natural products. These aminoloactones, which exhibit excellent activity against three pancreatic cancer cell lines when measured at 10 mu M-Panc-1, MIA PaCa-2, and BxPC-3-and are comparable to or better than parthenolide and dimethylaminoparthenolide (DMAPT, LC-1). It has also been shown that there is an effect on the biological activity depending on the identity of the amine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.09.065
• 作为产物：
  描述：

  苯甲醛 在 indium 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 cis-2-methylene-3,4-diphenylbutano-4-lactone
  参考文献：
  名称：

  通过介导的Barbier反应和MeSO 2 Cl / Et 3 N条件下的立体选择性内酯化，从Baylis-Hillman加合物高效合成α-亚甲基-γ-丁内酯

  摘要：

  的有效的合成反式-α亚甲基-γ丁内酯是从公开SYN加入MsCl / ET的影响下由附近的酯基通过促进分子内的甲磺酸酯置换反应-homoallylic醇3 N.顺-Homoallylic醇通过在制备介导的Baylis–Hillman加合物的溴化物的Barbier反应。

  DOI：

  10.1016/j.tetlet.2010.10.077

文献信息

• Diastereoselective synthesis of α-(aminomethyl)-γ-butyrolactones via a catalyst-free aminolactonization
  作者：P. Veeraraghavan Ramachandran、Daniel R. Nicponski

  DOI：10.1039/c4cc05765a

  日期：——

  An auto-catalytic domino reaction involving an aza-Michael reaction, proton transfer, and lactonization furnishing α-aminomethyl-γ-butyrolactones in near quantitative yields and excellent diastereoselectivity is described.

  一种涉及aza-Michael反应、质子转移和内酯化的自催化多米诺反应，以近定量的收率和优秀的对映选择性提供了α-氨基甲基-γ-丁内酯。

• 4-(Dimethylamino)pyridine as a catalyst for the lactonization of 4-hydroxy-2-methylenebutanoate esters
  作者：Daniel R. Nicponski

  DOI：10.1016/j.tetlet.2014.02.024

  日期：2014.3

  The catalytic action of 4-(dimethylamino)pyridine (DMAP) in lactonizing 4-hydroxy-2-methylenebutanoate esters to 2-methylene-γ-butyrolactones is described. The use of DMAP, which functions as an excellent complement to the more traditional acid-catalyzed lactonization protocol, allows for the synthesis of 2-methylene-γ-butyrolactones containing acid-sensitive groups under essentially neutral conditions

  描述了4-（二甲基氨基）吡啶（DMAP）在将4-羟基-2-亚甲基丁酸酯酯化为2-亚甲基-γ-丁内酯中的催化作用。DMAP的使用可作为对更传统的酸催化内酯化方法的出色补充，可以在基本上中性的条件下合成含有酸敏感基团的2-亚甲基-γ-丁内酯。
• β,γ-Diaryl α-methylene-γ-butyrolactones as potent antibacterials against methicillin-resistant Staphylococcus aureus
  作者：Henry J. Hamann、Nader S. Abutaleb、Rusha Pal、Mohamed N. Seleem、P. Veeraraghavan Ramachandran

  DOI：10.1016/j.bioorg.2020.104183

  日期：2020.11

  A selected series of racemic α-methylene-γ-butyrolactones (AMGBL) synthesized via allylboration or allylindation reactions were screened against methicillin-resistant Staphylococcus aureus (MRSA) USA300. Unlike natural AMGBLs, such as parthenolide, synthetic analogs bearing aryl moieties at the β- and γ-positions are potent against MRSA. The most potent molecules were comparable to vancomycin and linezolid

  筛选了通过烯丙基硼化或烯丙基化反应合成的一系列外消旋α-亚甲基-γ-丁内酯（AMGBL），以抗耐甲氧西林的金黄色葡萄球菌（MRSA）美国300。与天然的AMGBLs（例如，单苯二酚）不同，在β和γ位置带有芳基的合成类似物对MRSA具有有效的作用。最有效的分子在最小抑制浓度（MIC）为3.0至5.2μM的情况下，可与万古霉素和利奈唑胺（最后一种针对MRSA感染的药物）媲美。这些内酯还显示出对其他临床上重要的耐多药革兰氏阳性细菌（肠球菌除外）有效的抗菌活性，同时还显示出对哺乳动物细胞的高度耐受性。在标准的时间杀灭动力学分析中，这些分子中的几个在快速杀死高MRSA接种物（2 h和12 h）方面超过了万古霉素，化合物为1l和1m在低浓度下，可显着降低MRSA的细胞内负担约98–99％。此外，该化合物在抑制葡萄球菌蛋白酶产生方面超过了万古霉素，表明合成的亚甲基内酯作为有希望的抗MRSA候选物值得进一步研究。
• Stereoselective Radical Addition to .ALPHA.-Methylenebutyrolactones by Indirect Electroreduction Catalyzed by a Nickel(II) Complex.
  作者：Shigeko OZAKI、Eiki MATSUI、Hidenobu OHMORI

  DOI：10.1248/cpb.45.198

  日期：——

  The addition of butyl radicals to β- and/or γ-disubstituted α-methylenebutyrolactones by a nickel(II) complex-catalyzed indirect electroreduction using equimolar amounts of butyl iodides and α-methylenebutyrolactones provides cis-(C-α) : (C-β)-trisubstituted lactones as the major product. The addition was successful because the present method to permits long lifetimes for the initial butyl radicals and decreases lifetimes of the final adduct radicals by selective reduction of these radicals.

  通过镍(II)配合物催化，利用等摩尔量的碘代丁烷和α-亚甲基丁内酯进行间接电还原加成反应，可主要得到顺式-(C-α) : (C-β)-三取代的内酯。加成反应之所以成功，是因为当前方法允许初始丁基自由基具有较长的寿命，并通过选择性还原这些自由基，减少了最终加成产物自由基的寿命。
• Control of Stereochemistry:  A General Synthesis of <i>cis</i>- or <i>trans</i>-β,γ-Disubstituted-γ-butyrolactones Following <i>Z</i>-Crotylboration
  作者：P. Veeraraghavan Ramachandran、Debarshi Pratihar、Debanjan Biswas

  DOI：10.1021/ol061566g

  日期：2006.8.1

  [reaction; see text] A general and practical procedure for the highly diastereoselective preparation of either the cis- or trans-beta,gamma-disubstituted-gamma-butyrolactones by appropriate choice of Lewis or Bronsted acid catalysts during crotylboration or lactonization is reported. The cis-stereochemistry of the Z-crotylboration product can be inverted with strong acids during lactonization. A carbocation

  [反应; 见文]为顺式或反式-β-的高度非对映制备的一般和实用程序，则报告crotylboration或内酯化过程中的γ-二取代-γ丁内酯由路易斯或布朗斯台德酸催化剂的合适的选择。Z-巴豆基硼化产物的顺式立体化学可以在内酯化过程中用强酸逆转。已经提出了碳正离子化机理和催化循环。