6-hydroxymethyl-3-azabicyclo<3.2.0>hept-6-ene-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 6-hydroxymethyl-3-azabicyclo<3.2.0>hept-6-ene-2,4-dione
• 英文别名: 6-(hydroxymethyl)-3-azabicyclo[3.2.0]hept-6-ene-2,4-dione
• 化学式: C₇H₇NO₃
• 分子量: 153.137
• InChiKey: VWYPPACEJLSUBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  马来酰亚胺 、 2-丙炔-1-醇 以 乙腈 为溶剂， 反应 2.5h， 以65%的产率得到6-hydroxymethyl-3-azabicyclo<3.2.0>hept-6-ene-2,4-dione
  参考文献：
  名称：

  批处理与流式光化学：产率和生产率的显着比较

  摘要：

  近年来，许多小组已经报道了使用流动光化学及其明显优于批次的优势。为了严格确定流量是否确实比批次具有优势，在两种反应器模式下都对各种合成光化学转化进行了优化，并比较了它们的产率和生产率。出人意料的是，在所有比较情况下，产量基本相同。更加揭示的是，当关键反应参数相匹配时，流动反应器的生产率与其批次反应器的生产率变化很小。单层氟化乙烯丙烯（FEP）的平均生产率比间歇法低20％，而三层反应器的平均生产率高20％。最后，

  DOI：

  10.1002/chem.201404347

文献信息

• Stereoselective Intermolecular [2+2] photocycloaddition reactions of tetrahydrophthalic anhydride and derivatives with alkenols and alkynols
  作者：Kevin I. Booker-Milburn、Justin K. Cowell、F. Delgado Jiménez、Andrew Sharpe、Andrew J. White

  DOI：10.1016/s0040-4020(99)00250-1

  日期：1999.4

  Intermolecular [2+2] photocycloaddition of a variety of alken- and alkyn-3-ols with 3,4,5,6-tetrahydrophthalic anhydride (THPA) and the related imide (THPI) gave the corresponding cyclobutanes and cyclobutenes in high yield. Irradiation times were relatively short and stereoselectivities as high as for the cyclobutane examples.

  各种烯烃和炔-3-醇与3,4,5,6-四氢邻苯二甲酸酐（THPA）和相关酰亚胺（THPI）的分子间[2 + 2]光环加成反应可高产率地得到相应的环丁烷和环丁烯。辐射时间相对较短，立体选择性与环丁烷实例一样高。
• Batch versus Flow Photochemistry: A Revealing Comparison of Yield and Productivity
  作者：Luke D. Elliott、Jonathan P. Knowles、Paul J. Koovits、Katie G. Maskill、Michael J. Ralph、Guillaume Lejeune、Lee J. Edwards、Richard I. Robinson、Ian R. Clemens、Brian Cox、David D. Pascoe、Guido Koch、Martin Eberle、Malcolm B. Berry、Kevin I. Booker-Milburn

  DOI：10.1002/chem.201404347

  日期：2014.11.10

  The use of flow photochemistry and its apparent superiority over batch has been reported by a number of groups in recent years. To rigorously determine whether flow does indeed have an advantage over batch, a broad range of synthetic photochemical transformations were optimized in both reactor modes and their yields and productivities compared. Surprisingly, yields were essentially identical in all

  近年来，许多小组已经报道了使用流动光化学及其明显优于批次的优势。为了严格确定流量是否确实比批次具有优势，在两种反应器模式下都对各种合成光化学转化进行了优化，并比较了它们的产率和生产率。出人意料的是，在所有比较情况下，产量基本相同。更加揭示的是，当关键反应参数相匹配时，流动反应器的生产率与其批次反应器的生产率变化很小。单层氟化乙烯丙烯（FEP）的平均生产率比间歇法低20％，而三层反应器的平均生产率高20％。最后，
• Tetrahydrophthalic anhydride and imide: remarkably efficient partners in photochemical [2 + 2] cycloaddition reactions with alkenols and alkynols
  作者：Kevin I. Booker-Milburn、Justin K. Cowell、Andrew Sharpe、F. Delgado Jiménez

  DOI：10.1039/cc9960000249

  日期：——

  Intermolecular photochemical [2 + 2] cycloaddition of a variety of alken- and alkyn-3-ols with 3,4,5,6-tetrahydrophthalic anhydride (THPA) and the related imide 4 gave the corresponding cyclobutanes and cyclobutenes in high yield, after relatively short irradiation times, with stereoselectivities as high as 10:1 for the cyclobutane examples.
• A Small-Footprint, High-Capacity Flow Reactor for UV Photochemical Synthesis on the Kilogram Scale
  作者：Luke D. Elliott、Malcolm Berry、Bashir Harji、David Klauber、John Leonard、Kevin I. Booker-Milburn

  DOI：10.1021/acs.oprd.6b00277

  日期：2016.10.21

  The development of a highly compact and powerful reactor for synthetic organic photochemistry is described enabling a 10-fold reduction in reaction times, with up to 30% more power efficiency than previous fluorinated ethylene propylene tube reactors. Two reactions gave over 1 kg of product in 24 h. Two other reactions had productivities of 4 and 8 kg in 24 h. The reactor consists of a succession of quartz tubes connected together in series and arranged axially around a variable power mercury lamp. This compact and relatively simple device can be safely operated in a standard fumehood.
• A Photochemical Microfluidic Reactor for Photosensitized [2+2] Cycloadditions
  作者：Luca Laraia、Martin Bargum、Mikkel Krell-Jørgensen、Martin Nielsen、Katrine Qvortrup

  DOI：10.1055/a-1771-4883

  日期：2022.7

  Here we report a microfluidic system for photochemical cycloadditions fabricated using silicon micro processing technologies. The system was optimized to yield residence times of just a few minutes for a range of photochemical [2+2]-cycloaddition reactions facilitated using high power UV-LEDs at 375 nm and triplet photosensitizers, which removed the need for the low wavelengths typically required for

  在这里，我们报告了一种使用硅微加工技术制造的光化学环加成微流控系统。该系统经过优化，使用 375 nm 的高功率 UV-LED 和三重态光敏剂促进了一系列光化学 [2+2]-环加成反应的停留时间仅为几分钟，从而消除了对通常所需的低波长的需求对于这些类型的转换。探索了使用具有不同线性、碳环和杂环偶联伙伴的不同可激发烯烃的加合物，以证明在学术研究环境中在微流中进行光化学的可行性。最后，报告了导致新型 dihydrooxepin-2(3 H )-one 支架的反应及其形成的机制建议。