2-(but-2-en-1-yl) isoindoline-1,3-dione | 156382-60-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(but-2-en-1-yl) isoindoline-1,3-dione
• 英文别名: cis-N-crotylphthalimide；N-but-2c-enyl-phthalimide；N-But-2c-enyl-phthalimid；2-[(Z)-but-2-enyl]isoindole-1,3-dione
• CAS: 156382-60-4
• 化学式: C₁₂H₁₁NO₂
• 分子量: 201.225
• InChiKey: PMUYLAJCELXRCO-IHWYPQMZSA-N

物化性质

• 熔点：
  66-66.5 °C(Solv: ethanol, 50% (64-17-5))
• 沸点：
  314.5±21.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(but-2-en-1-yl) isoindoline-1,3-dione 在 乙醇 、 一水合肼 作用下， 生成 3-甲基-2-丙烯基胺
  参考文献：
  名称：

  The Mustard Oil of Rape Seed, Allylcarbinyl Isothiocyanate, and Synthetic Isomers

  摘要：

  DOI：

  10.1021/ja01612a035
• 作为产物：
  描述：

  1-苯二酰亚氨基-2-丁炔 在 喹啉 、 lead 、 钯 、 乙酸乙酯 作用下， 生成 2-(but-2-en-1-yl) isoindoline-1,3-dione
  参考文献：
  名称：

  The Mustard Oil of Rape Seed, Allylcarbinyl Isothiocyanate, and Synthetic Isomers

  摘要：

  DOI：

  10.1021/ja01612a035

文献信息

• A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols
  作者：Joseph B. Sweeney、Anthony K. Ball、Philippa A. Lawrence、Mackenzie C. Sinclair、Luke J. Smith

  DOI：10.1002/anie.201805611

  日期：2018.8.6

  inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron‐deficient amines without the need for glove‐box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron‐deficient nitrogen nucleophiles; the

  传统上，烯丙基胺的制备是通过胺与反应性亲电试剂，例如烯丙基卤化物，磺酸盐或氧phosph物种的反应来完成的。这样的方法涉及危险试剂，产生化学计量的废物流，并且经常遭受副反应（例如烷基化过度）。我们在这里报告了第一项广谱镍催化的烯丙醇直接胺化反应：一种廉价的Ni II/ Zn对可实现伯胺，仲胺和电子不足的胺的烯丙基化，而无需使用手套箱技术。在温和的条件下，伯和仲脂族胺与一系列烯丙醇均能平稳反应，从而有效地生成仲和叔胺。这种“完全催化”的方法也可以应用于缺电子的氮亲核试剂。该方法的实用性在高效，克级的钙拮抗剂药物氟那利嗪（Sibelium®）的制备中得到了证明。
• <i>N</i>-Allylation of Imides Catalyzed by Palladium(0)
  作者：Yoshio Inoue、Masaaki Taguchi、Masanori Toyofuku、Harukichi Hashimoto

  DOI：10.1246/bcsj.57.3021

  日期：1984.10

  Palladium(0)–triphenylphosphine complexes catalyzed the allylic exchange reaction of allylic esters, phenyl ethers, and isoureas with imides such as phthalimide to give N-allylic products. Among them, O-allylic isoureas were most effective in exchanging the allylic group of more complex structure. N-Allylic derivatives were also obtained by the telomerization of butadiene or allene with phthalimide

  钯（0）-三苯基膦配合物催化烯丙酯、苯基醚和异脲与酰亚胺（如邻苯二甲酰亚胺）的烯丙基交换反应，得到 N-烯丙基产物。其中，O-烯丙基异脲最有效地交换更复杂结构的烯丙基。N-烯丙基衍生物也可通过丁二烯或丙二烯与邻苯二甲酰亚胺在钯 (0) 物种催化下的调聚反应获得。
• PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20140194604A1

  公开（公告）日：2014-07-10

  The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C 2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.

  本发明涉及将内烯烃氧化为酮的方法。在各种实施方式中，每种方法包括将具有初始内烯烃的有机底物与（a）双阳离子钯盐的混合物；和（b）氧化剂接触，溶解或分散在溶剂体系中形成反应混合物，所述溶剂体系包括至少一种C2-6碳腈和可选地至少一种次烷基酰胺，所述方法在足以将初始内烯烃的至少50摩尔％转化为酮的条件下进行，所述酮位于初始内烯烃的碳上。该转化在室温下发生，并显示出广泛的底物范围。描述了将其应用于种子油衍生物和生物活性天然产物的氧化。
• A Pd-Catalyzed Site-Controlled Isomerization of Terminal Olefins
  作者：Wenlong Ren、Fei Sun、Jianxiao Chu、Yian Shi

  DOI：10.1021/acs.orglett.0c00168

  日期：2020.3.6

  An effective Pd-catalyzed isomerization of olefins with 2-PyPPh2 as the ligand is described. A wide variety of trans-2-olefins bearing various functional groups can be obtained with high regio- and stereoselectivity under mild reaction conditions. The ligand is crucial for the reaction.

  描述了以2-PyPPh2作为配体的烯烃的有效Pd催化异构化。在温和的反应条件下，可以以高区域选择性和立体选择性获得具有各种官能团的各种反式-2-烯烃。配体对于反应至关重要。
• EFFICIENT METHODS FOR Z- OR CIS-SELECTIVE CROSS-METATHESIS
  申请人：Hoveyda Amir H.

  公开号：US20110245477A1

  公开（公告）日：2011-10-06

  The present invention generally relates to methods for performing metathesis reactions, including cross-metathesis reactions. Methods described herein exhibit enhanced activity and stereoselectivity, relative to known methods, and are useful in the synthesis of a large assortment of biologically and therapeutically significant agents.

  本发明一般涉及执行交换反应的方法，包括交叉交换反应。本文所描述的方法相对于已知方法表现出增强的活性和立体选择性，并且在合成大量生物学和治疗学上重要的制剂方面是有用的。