N,N-Bis(5-chloro-3-oxo-1,2-dithiol-4-yl)(2-phthalimidoethyl)amine | 250379-54-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-Bis(5-chloro-3-oxo-1,2-dithiol-4-yl)(2-phthalimidoethyl)amine
• 英文别名: 2-[2-[Bis(3-chloro-5-oxodithiol-4-yl)amino]ethyl]isoindole-1,3-dione
• CAS: 250379-54-5
• 化学式: C₁₆H₈Cl₂N₂O₄S₄
• 分子量: 491.421
• InChiKey: ARTSOXYINLYNAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  176
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N,N-Bis(5-chloro-3-oxo-1,2-dithiol-4-yl)(2-phthalimidoethyl)amine 在 二氯化二硫 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以95%的产率得到4-(2-phthalimidoethyl)bis[1,2]dithiolo[3,4-b:4',3'-e][1,4]thiazine-3,5-dione
  参考文献：
  名称：

  Selective synthesis of bis[1,2]dithiolo[1,4]thiazines from 4-isopropylamino-5-chloro-1,2-dithiole-3-ones

  摘要：

  Reaction of 4-isopi-opylamiiio-5-chloro-1,2-dithiole-3-oiies 3 and S2Cl2 in acetonitrile gave selectively 3-oxo-bis[1,2]dithiolo[1,4]tliiazine-5-tiliones I by the addition of triethylamine and bis[1,2]dithiolo[1,4]thiazine-3,5-diones 5 under the action of formic acid. 3,5-Diones 5 were also obtained by intramolecular cyclization of N,N-bis(5-chloro-3-oxo[1,2]dithiol-4-yl)amines 6 with S,Cl, in the presence of Et3N. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.071
• 作为产物：
  描述：

  N-(2-phthalimidoethyl)diisopropylamine 在 三乙烯二胺 、 二氯化二硫 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 98.0h， 生成 N,N-Bis(5-chloro-3-oxo-1,2-dithiol-4-yl)(2-phthalimidoethyl)amine
  参考文献：
  名称：

  Selective synthesis of bis[1,2]dithiolo[1,4]thiazines from 4-isopropylamino-5-chloro-1,2-dithiole-3-ones

  摘要：

  Reaction of 4-isopi-opylamiiio-5-chloro-1,2-dithiole-3-oiies 3 and S2Cl2 in acetonitrile gave selectively 3-oxo-bis[1,2]dithiolo[1,4]tliiazine-5-tiliones I by the addition of triethylamine and bis[1,2]dithiolo[1,4]thiazine-3,5-diones 5 under the action of formic acid. 3,5-Diones 5 were also obtained by intramolecular cyclization of N,N-bis(5-chloro-3-oxo[1,2]dithiol-4-yl)amines 6 with S,Cl, in the presence of Et3N. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.071

文献信息

• Conversion of N-alkyldiisopropylamines into N,N-bis(5-chloro-3-oxo[1,2]dithiol-4-yl)amines
  作者：Susana Barriga、Lidia S. Konstantinova、Carlos F. Marcos、Oleg A. Rakitin、Charles W. Rees、Tomás Torroba、Andrew J. P. White、David J. Williams

  DOI：10.1039/a904680a

  日期：——

  Triisopropylamine 1a and S2Cl2, in the presence of DABCO and formic acid, give the bicyclic amine 2a, and its N-dealkylated product 3, rather than the tricyclic bisdithiolothiazine system 7 produced by Hünig’s base 1b. However, when S2Cl2 is in molar excess over DABCO, Hünig’s base and related N-alkyldiisopropylamines 1c–g also give the analogous bicyclic compounds 2b–g together with the tricyclic compounds 7b–g. The N-benzyl compound 2c is debenzylated quantitatively to the secondary amine 3 by sulfuric acid. X-Ray crystallography of N,N-bis(dithiolyl)ethylamine 2b shows the two dithiole rings to be steeply inclined to each other (85°) and the geometry at nitrogen to be slightly pyramidal. The crystal packing is dominated by S· · ·O electrostatic and weak CO· · ·Cl charge-transfer interactions.

  在DABCO和甲酸的存在下，三异丙胺1a与S2Cl2反应生成双环胺2a及其N-去烷基化产物3，而不是由Hünig碱1b产生的三环双二硫氮杂环庚烷体系7。然而，当S2Cl2的摩尔过量于DABCO时，Hünig碱及相关N-烷基二异丙胺1c–g也能生成类似的双环化合物2b–g以及三环化合物7b–g。N-苄基化合物2c可通过硫酸定量去苄基化转化为二级胺3。N,N-双(二硫烷基)乙胺2b的X射线晶体学显示，两个二硫烷环彼此陡峭地倾斜（85°），氮原子周围的几何形状略呈锥形。晶体堆积主要受S··O静电作用和弱的CO··Cl电荷转移相互作用支配。