dimethyl 2-(6-(((4-methylphenyl)sulfonamido)methyl)benzo[d][1,3]dioxol-5-yl)malonate | 1210801-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2-(6-(((4-methylphenyl)sulfonamido)methyl)benzo[d][1,3]dioxol-5-yl)malonate
• 英文别名: Dimethyl 2-[6-[[(4-methylphenyl)sulfonylamino]methyl]-1,3-benzodioxol-5-yl]propanedioate
• CAS: 1210801-54-9
• 化学式: C₂₀H₂₁NO₈S
• 分子量: 435.455
• InChiKey: JAROMIKMIRGJQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  dimethyl 2-(6-(((4-methylphenyl)sulfonamido)methyl)benzo[d][1,3]dioxol-5-yl)malonate 、 3-丁炔-2-酮 在 1,3-双(二苯基膦)丙烷 作用下， 以 乙腈 为溶剂， 反应 36.0h， 以82%的产率得到Dimethyl 6-(4-methylphenyl)sulfonyl-7-(2-oxopropyl)-5,7-dihydro-[1,3]dioxolo[4,5-g]isoquinoline-8,8-dicarboxylate
  参考文献：
  名称：

  Diphosphine-Catalyzed Mixed Double-Michael Reaction: A Unified Synthesis of Indolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1-oxazines

  摘要：

  Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridines, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinucleophiles and electron-deficient acetylenes in one synthetic step. This powerful methodology was made possible through the use of diphenylphosphinopropane (DPPP) as the catalyst, with acetic acid and sodium acetate used as additives in some cases. The benzannulated N-heterocycles were isolated in excellent yields under mild metal-free conditions; they were purified without the need for aqueous workups.

  DOI：

  10.1021/ol100078w
• 作为产物：
  描述：

  N-((6-iodobenzo[d][1,3]dioxol-5-yl)methyl)-4-methylbenzenesulfonamide 、 丙二酸二甲酯 在 2-吡啶甲酸 、 copper(l) iodide 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以39%的产率得到dimethyl 2-(6-(((4-methylphenyl)sulfonamido)methyl)benzo[d][1,3]dioxol-5-yl)malonate
  参考文献：
  名称：

  通过手性α，β-不饱和酰基铵盐对中内酰胺的对映选择性合成

  摘要：

  中型内酰胺是在多种生物活性化合物和天然产物中发现的重要结构基序，但制备难度很大，尤其是以光学活性形式存在。描述了一种迈克尔加成/质子转移/内酰胺化有机级联过程，该过程通过手性α，β-不饱和酰基salts盐的中间产物以高对映体纯度输送中等大小的内酰胺，包括a庚酮，苯并enza庚酮，偶氮烷酮和苯并偶氮酮。还发现了意外的二氢吲哚合成，并将苯并偶氮酮骨架转化为其他复杂的杂环衍生物，包括螺戊二酰亚胺，异喹啉酮和δ-内酯。

  DOI：

  10.1002/anie.201802483

文献信息

• Diphosphine-Catalyzed Mixed Double-Michael Reaction: A Unified Synthesis of Indolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1-oxazines
  作者：Vardhineedi Sriramurthy、Ohyun Kwon

  DOI：10.1021/ol100078w

  日期：2010.3.5

  Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridines, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinucleophiles and electron-deficient acetylenes in one synthetic step. This powerful methodology was made possible through the use of diphenylphosphinopropane (DPPP) as the catalyst, with acetic acid and sodium acetate used as additives in some cases. The benzannulated N-heterocycles were isolated in excellent yields under mild metal-free conditions; they were purified without the need for aqueous workups.
• Enantioselective Synthesis of Medium‐Sized Lactams via Chiral α,β‐Unsaturated Acylammonium Salts
  作者：Guowei Kang、Masaki Yamagami、Sreekumar Vellalath、Daniel Romo

  DOI：10.1002/anie.201802483

  日期：2018.5.28

  challenging to prepare, especially in optically active form. A Michael addition/proton transfer/lactamization organocascade process is described that delivers medium‐sized lactams, including azepanones, benzazepinones, azocanones, and benzazocinones, in high enantiopurity through the intermediacy of chiral α,β‐unsaturated acylammonium salts. An unexpected indoline synthesis was also uncovered, and the benzazocinone

  中型内酰胺是在多种生物活性化合物和天然产物中发现的重要结构基序，但制备难度很大，尤其是以光学活性形式存在。描述了一种迈克尔加成/质子转移/内酰胺化有机级联过程，该过程通过手性α，β-不饱和酰基salts盐的中间产物以高对映体纯度输送中等大小的内酰胺，包括a庚酮，苯并enza庚酮，偶氮烷酮和苯并偶氮酮。还发现了意外的二氢吲哚合成，并将苯并偶氮酮骨架转化为其他复杂的杂环衍生物，包括螺戊二酰亚胺，异喹啉酮和δ-内酯。