2-氯-3-吡咯烷基-1,4-萘醌 | 59641-25-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-氯-3-吡咯烷基-1,4-萘醌
• 英文名称: 2-chloro-3-(pyrrolidin-1-yl)-1,4-naphthoquinone
• 英文别名: 2-Chloro-3-pyrrolidino-1,4-naphthoquinone；2-chloro-3-(pyrrolidin-1-yl)naphthalene-1,4-dione；2-chloro-3-pyrrolidin-1-ylnaphthalene-1,4-dione
• CAS: 59641-25-7
• 化学式: C₁₄H₁₂ClNO₂
• 分子量: 261.708
• InChiKey: QWKZKEUBFVSTDB-UHFFFAOYSA-N

物化性质

• 熔点：
  101-103 °C(lit.)
• 沸点：
  368.1±42.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• 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：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38

反应信息

• 作为反应物：
  描述：

  2-氯-3-吡咯烷基-1,4-萘醌 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  A general strategy for visible-light decaging based on the quinone cis-alkenyl lock

  摘要：

  将对羟基肉桂酸衍生物的快速热环化与醌的分子内光还原相结合，可得到新的可见光光解保护基，其吸收波长远超过450纳米。

  DOI：

  10.1039/c9cc01073d
• 作为产物：
  描述：

  四氢吡咯 、 2,3-二氯-1,4-萘醌 在 水 作用下， 反应 0.17h， 以99%的产率得到2-氯-3-吡咯烷基-1,4-萘醌
  参考文献：
  名称：

  “在水上”：在水悬浮液中与1,4-醌进行前所未有的亲核取代和加成反应

  摘要：

  在没有传统合成催化剂的催化剂的情况下，描述了水性悬浮液中1,4-醌与芳香胺，伯脂肪胺，氨基酸，氨基酸酯，杂环胺，肼，酰胺和硫醚的独特亲核取代和加成反应催化剂存在下在非水介质中进行这些反应的途径。

  DOI：

  10.1016/j.tetlet.2009.07.149

文献信息

• 2-(Pyrrolidin-1-yl)-1,4-naphthoquinone and 2-phenylsulfanyl-3-(pyrrolidin-1-yl)-1,4-naphthoquinone
  作者：Daniel E. Lynch、Ian McClenaghan

  DOI：10.1107/s0108270102019194

  日期：2002.12.15

  The structure of 2-(pyrrolidin-1-yl)-1,4-naphthoquinone, C(14)H(12.9)5Cl(0.05)NO(2), (I), is actually a 0.95:0.05 mixture including 2-chloro-3-(pyrrolidin-1-yl)-1,4-naphthoquinone as a minor impurity, but (I) was resolved as a single molecule containing a Cl atom with 5% occupancy at the 3-position. Compound (I) was prepared from the fully chloro-substituted analogue in an attempt to produce the disubstituted pyrrolidinyl derivative. 2-Phenylsulfanyl-3-(pyrrolidin-1-yl)1,4-naphthoquinone, C20H17NO2S, (II), was also prepared from 2-chloro-3-(pyrrolidin-1-yl)-1,4-naphthoquinone, using a strong exocyclic nucleophile. The structure of (II) differs from previous structures of 2,3-dichloro-1,4-naphthoquinone and its derivatives in that the naphthoquinone ring is non-planar.
• ‘On water’ assisted synthesis and biological evaluation of nitrogen and sulfur containing hetero-1,4-naphthoquinones as potent antifungal and antibacterial agents
  作者：Vishnu K. Tandon、Hardesh K. Maurya、Manoj K. Verma、Rohitashw Kumar、Praveen K. Shukla

  DOI：10.1016/j.ejmech.2010.02.023

  日期：2010.6

  2-Chloro-3-(4-methylpiperazin-1-yl)naphthalene-1,4-dione (3a), 2-chloro-3-(pyrrolidin-1-yl)naphthalene-1,4-dione (3b), 2-chloro-3-(piperidin-1-yl)naphthalene-1,4-dione (3c), 2-chloro-3-morpholinonaphthalene-1,4-dione (3d), 2-chloro-3-(2-phenylhydrazinyl)naphthalene-1,4-dione (3e), 2-(allylamino)-3-chloronaphthalene-1,4-dione (3f), 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)acetic acid (3g), 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)succinic acid (3h), methyl 2-(3-chloro-1,4-choxo-1,4-dihydronaphthalen-2-ylthio)acetate (3i), 2-chloro-3-(2-mercaptoethylthio)naphthalene-1,4-dione (3j), 3-hydroxy-4-methyl-4H-naphtho[2,3-b][1,4]thiazine-5,10-dione (3k) and compounds 31-q have been synthesized by a green methodology approach using water as solvent and evaluated for their antifungal and antibacterial activity. The antifungal profile of 3a-n indicated that compounds 3a-d, 3j, 3e and 3k have potent antifungal activity. Amongst the most promising antifungal compounds, 3a-g, 3j, 3k showed better antifungal activity than clinically prevalent antifungal drugs Fluconazole and Amphotericin-B against Trichophyton mentagraphytes and compounds 3j and 3k have been found to be lead antifungal bicyclic and tricyclic 1,4-naphthoquinones. Compound 3k also exhibited pronounced antibacterial activity.
• US5684035A
  申请人：——

  公开号：US5684035A

  公开（公告）日：1997-11-04
• US5807898A
  申请人：——

  公开号：US5807898A

  公开（公告）日：1998-09-15

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