2-(3,4-Methylenedioxyphenyl)acetic pivalic anhydride | 250261-64-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(3,4-Methylenedioxyphenyl)acetic pivalic anhydride
• 英文别名: (3,4-Methylenedioxyphenyl)acetic pivalic anhydride；[2-(1,3-Benzodioxol-5-yl)acetyl] 2,2-dimethylpropanoate
• CAS: 250261-64-4
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: WQWQGTMUGZTJJY-UHFFFAOYSA-N

物化性质

• 沸点：
  361.4±21.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3,4-Methylenedioxyphenyl)acetic pivalic anhydride 在 palladium on activated charcoal 吡啶 、 aluminium hydride 、 盐酸 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 氢气 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 正己烷 、 苯 为溶剂， 反应 26.0h， 生成 (4aS*,11R*,11aS*)-8,9-Methylenedioxy-5,11-methanomorphanthridine
  参考文献：
  名称：

  Stereoselective synthesis of (3R*,3aS*,7aS*)-3-aryloctahydroindol-2-ones using radical cyclisation: a formal synthesis of (±)-pancracine

  摘要：

  Bu3SnH 或 (TMS)3SiH 介导的 N-(环己-1-烯基)乙酰胺 10 的 5-endo-trig 自由基环化反应生成顺式融合的 (3R*,3aS*,7aS*)- 和反式融合的 (3R*,3aS*,7aR*)-3-芳基八氢吲哚-2-酮 11a 和 11b 的混合物，而 N-(环己-2-烯基)乙酰胺 17 的 5-exo-trig 自由基环化反应则以立体选择性方式进行，仅生成 11a。后者方法已应用于合成 5,11-甲基吗啡啉衍生物 30，这是合成 (±)-潘克拉辛 1 的关键中间体。

  DOI：

  10.1039/a900467j
• 作为产物：
  描述：

  胡椒乙酸 生成 2-(3,4-Methylenedioxyphenyl)acetic pivalic anhydride
  参考文献：
  名称：

  Tetrahedron Lett. 1999, 40, 7175-7178

  摘要：

  DOI：

文献信息

• Unusual Magnesium Chloride Catalyzed Non-Evansanti-Aldol Reactions of an EnolizableL-Threose Derivative
  作者：James McNulty、Jerald J. Nair、Marcin Sliwinski、Laura E. Harrington、Siyaram Pandey

  DOI：10.1002/ejoc.200700854

  日期：2007.12

  The magnesium chloride catalyzed anti-aldol reaction of phenyl acetate derived oxazolidinones proceeds readily with enolizable L-threose derivative 8 to provide anti-aldol adducts in high yields and with very high diastereoselectivities. The reaction is also efficient with aromatic aldehydes and provides slightly lower diastereoselectivities. This extension

  乙酸苯酯衍生的恶唑烷酮的氯化镁催化的抗羟醛反应容易与可烯醇化的 L-苏糖衍生物 8 进行，以高产率和非常高的非对映选择性提供抗羟醛加合物。该反应对芳香醛也有效，并提供稍低的非对映选择性。这个扩展
• Formal Synthesis of (±)-Pancracine Using Stereoselective Radical Cyclization of <i>N</i>-(2-Cyclohexenyl)-<i>α</i>-aryl-<i>α</i>-(phenylthio)acetamide
  作者：Masazumi Ikeda

  DOI：10.1055/s-1998-1937

  日期：1998.11
• Stereoselective α-Fluorination of <i>N</i>-Acyloxazolidinones at Room Temperature within 1 h
  作者：Joseph Alvarado、Aaron T. Herrmann、Armen Zakarian

  DOI：10.1021/jo500957d

  日期：2014.7.3

  A direct alpha-fluorination of N-acyloxazolidinones based on the unique reactivity of group IVa metal enolates has been developed. The reaction is an experimentally simple, low-cost, quick, and energy-efficient alternative for asymmetric alpha-fluorination of N-acyloicazolidinones. Preliminary studies have shown compatibility with alkyl, alkenyl, and alkynyl, aromatic, and several heteroaromatic substituents. High diastereoselectivities have been achieved with most substrates tested, and the reaction is typically complete within 1 h at ambient temperature.
• Synthesis and Biological Evaluation of Fully Functionalized <i>seco</i>-Pancratistatin Analogues
  作者：James McNulty、Jerald J. Nair、Carly Griffin、Siyaram Pandey

  DOI：10.1021/np0705460

  日期：2008.3.1

  The total synthesis of fully functionalized polyhydroxyamide B,C-seco-analogues of the anticancer compound pancratistatin (PST) (1) is reported. Key steps include an Evans' MgCl2-promoted anti-aldol reaction between a functionalized L-threose derivative and (R)-(+)-oxazolidinone to stereoselectively form the C-1/C-10b bond and a regiospecific radical-mediated oxidative fragmentation of a 1,3-benzylidene. The B,C-seco compounds 25 and 26 exhibited low activity (ED50 > 30 yg/mL) for inducing apoptosis in human cancer cells.
• Structure–activity studies on seco-pancratistatin analogs: Potent inhibitors of human cytochrome P450 3A4
  作者：James McNulty、Jerald J. Nair、Mohini Singh、Denis J. Crankshaw、Alison C. Holloway

  DOI：10.1016/j.bmcl.2009.08.032

  日期：2009.10

  Two total syntheses of fully functionalized seco-analogs of the anticancer compound pancratistatin are reported. Structure-activity relationship (SAR) studies identified potent and selective inhibitors of human cytochrome P450 3A4 (CYP3A4) and revealed several core pharmacophoric elements. These studies identify potential roadblocks and will guide the further development of a viable selective clinical pancratistatin derivative. (C) 2009 Elsevier Ltd. All rights reserved.