2-(3,3-Dimethylbut-1-ynyl)isoindole-1,3-dione | 1313233-00-9

• 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-(3,3-Dimethylbut-1-ynyl)isoindole-1,3-dione
• 英文别名: 2-(3,3-dimethylbut-1-ynyl)isoindole-1,3-dione
• CAS: 1313233-00-9
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: XRTKQMRODCCZFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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-(3,3-Dimethylbut-1-ynyl)isoindole-1,3-dione 在 copper(l) chloride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 1-[2-[5-(1,1-dimethylethyl)-2-oxazolyl]phenyl]ethanone
  参考文献：
  名称：

  由N-炔基邻苯二甲酰亚胺生成的N-炔基-3-羟基异吲哚啉-1-酮的铜催化串联脱环-环化反应：邻-（2-恶唑基）苯基酮的选择性合成。

  摘要：

  用有机金属试剂在N-炔基邻苯二甲酰亚胺上进行选择性嗜碳单加成反应，得到3-取代的N-炔基-3-羟基异吲哚啉-1-酮（α-羟基乙酰胺），作为新的乙酰胺基。由于氮原子上的炔基基序，在温和的条件下，CuCl催化的串联脱环-环化反应中，α-羟基乙酰胺很容易异构化为相应的邻-（2-恶唑基）苯基酮。

  DOI：

  10.1021/acs.joc.6b00888
• 作为产物：
  描述：

  邻苯二甲酸亚胺 、 3,3-dimethyl-1-butynyl[tri(4-methylphenyl)]bismuthonium tetrafluoroborate 在 三乙胺 、 copper(I) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以75%的产率得到2-(3,3-Dimethylbut-1-ynyl)isoindole-1,3-dione
  参考文献：
  名称：

  N-Alkynyl Imides (Ynimides): Synthesis and Use as a Variant of Highly Labile Ethynamine

  摘要：

  This study describes the first reliable synthesis of N-alkynyl imides (ynimides). This was accomplished with a copper-catalyzed coupling reaction between alkynyl(triaryl)bismuthonium salts and five-membered imides. We also found that it was possible to utilize N-ethynyl phthalimide as a variant of the highly labile ethynamine. 4-Amino-1,2,3-triazole was successfully obtained via the CuAAC reaction of N-ethynyl phthalimide with azide followed by hydrazinolysis of the phthaloyl protecting group.

  DOI：

  10.1021/ol2014973

文献信息

• Ag- and Au-Catalyzed Addition of Alcohols to Ynimides: β-Regioselective Carbonylation and Production of Oxazoles
  作者：Takuya Sueda、Arisa Kawada、Yumi Urashi、Naoki Teno

  DOI：10.1021/ol400338x

  日期：2013.4.5

  Metal-catalyzed reactions of ynimides with alcohols to afford β-ketoimides and oxazoles are demonstrated. The triple bond of ynamides is generally activated by mineral acids or metal salts to lead to the regioselective addition of nucleophiles at the α-C-atom, because of the inherent electronic bias. In contrast, the two neighboring carbonyl groups of ynimides decrease the electron density of the triple

  证明了酰亚胺与醇的金属催化反应，得到β-酮酰亚胺和恶唑。乙酰胺的三键通常被无机酸或金属盐激活，从而由于固有的电子偏压而导致亲核试剂在α-C原子上的区域选择性加成。相反，酰亚胺的两个相邻的羰基降低了三键的电子密度，亲核试剂攻击了羰基C原子。
• <i>N</i>-Alkynyl Imides (Ynimides): Synthesis and Use as a Variant of Highly Labile Ethynamine
  作者：Takuya Sueda、Ayumi Oshima、Naoki Teno

  DOI：10.1021/ol2014973

  日期：2011.8.5

  This study describes the first reliable synthesis of N-alkynyl imides (ynimides). This was accomplished with a copper-catalyzed coupling reaction between alkynyl(triaryl)bismuthonium salts and five-membered imides. We also found that it was possible to utilize N-ethynyl phthalimide as a variant of the highly labile ethynamine. 4-Amino-1,2,3-triazole was successfully obtained via the CuAAC reaction of N-ethynyl phthalimide with azide followed by hydrazinolysis of the phthaloyl protecting group.
• Copper-Catalyzed Tandem Decyclization-Cyclization Reaction of <i>N</i>-Alkynyl-3-hydroxyisoindolin-1-ones Generated from <i>N</i>-Alkynyl Phthalimides: Selective Synthesis of <i>ortho</i>-(2-Oxazolyl)phenyl Ketones
  作者：Takuya Sueda、Noriko Okamoto、Reiko Yanada

  DOI：10.1021/acs.joc.6b00888

  日期：2016.7.1

  ynamides) as a new subgroup of ynamides. Owing to the alkynyl motif on the nitrogen atom, alpha-hydroxy ynamides were easily isomerized to the corresponding ortho-(2-oxazolyl)phenyl ketones in a CuCl-catalyzed tandem decyclization-cyclization reaction under mild conditions.

  用有机金属试剂在N-炔基邻苯二甲酰亚胺上进行选择性嗜碳单加成反应，得到3-取代的N-炔基-3-羟基异吲哚啉-1-酮（α-羟基乙酰胺），作为新的乙酰胺基。由于氮原子上的炔基基序，在温和的条件下，CuCl催化的串联脱环-环化反应中，α-羟基乙酰胺很容易异构化为相应的邻-（2-恶唑基）苯基酮。