ethyl 2'-amino-7',7'-dimethyl-2,5'-dioxo-5',6',7',8'-tetrahydro-2H-spiro[acenaphthylene-1,4'-chromene]-3'-carboxylate | 1197994-93-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl 2'-amino-7',7'-dimethyl-2,5'-dioxo-5',6',7',8'-tetrahydro-2H-spiro[acenaphthylene-1,4'-chromene]-3'-carboxylate
• 英文别名: Ethyl 2'-amino-7',7'-dimethyl-2,5'-dioxo-5',6',7',8'-tetrahydro-2h-spiro[acenaphthylene-1,4'-chromene]-3'-carboxylate；ethyl 2-amino-7,7-dimethyl-2',5-dioxospiro[6,8-dihydrochromene-4,1'-acenaphthylene]-3-carboxylate
• CAS: 1197994-93-6
• 化学式: C₂₅H₂₃NO₅
• 分子量: 417.461
• InChiKey: UDKJVZIYBJOXRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 氰乙酸乙酯 、 苊醌 在 polycyclic aromatic carbon sheets with sulfonic acid 作用下， 以 乙醇 为溶剂， 反应 3.5h， 以90%的产率得到ethyl 2'-amino-7',7'-dimethyl-2,5'-dioxo-5',6',7',8'-tetrahydro-2H-spiro[acenaphthylene-1,4'-chromene]-3'-carboxylate
  参考文献：
  名称：

  Carbon–SO 3 H：新型可循环利用的固体酸催化剂，用于合成螺[4 H -pyran-3,3'-oxindoles]

  摘要：

  已发现生物甘油衍生的碳磺酸可有效催化伊斯丁，丙二腈和1,3-二羰基的三组分一锅缩合，从而提供广泛的螺[4H-吡喃-3,3'-羟吲哚]衍生物具有良好的产率和选择性。可循环使用的固体酸催化剂的使用使该方法简单，方便且具有成本效益。

  DOI：

  10.1016/j.tetlet.2013.02.089

文献信息

• One-Pot Synthesis of Biologically Important Spiro-2-amino-4<i>H</i>-pyrans, Spiroacenaphthylenes, and Spirooxindoles Using DBU as a Green and Recyclable Catalyst in Aqueous Medium
  作者：Pooja Saluja、Komal Aggarwal、Jitender M. Khurana

  DOI：10.1080/00397911.2012.760130

  日期：2013.12.17

  Abstract We have reported DBU-catalyzed one-pot synthesis of biologically and pharmacologically important spiropyrans from condensation of malononitrile/ethyl cyanoacetate, 1,3-dicarbonyl compounds, and ninhydrin/acenaphthequinone/istain in good yields. This new protocol employing DBU, which is a green, recyclable, and inexpensive catalyst, offers advantages such as mild reaction conditions, short

  摘要 我们已经报道了 DBU 催化从丙二腈/氰基乙酸乙酯、1,3-二羰基化合物和茚三酮/苊醌/伊斯坦酮缩合合成具有生物学和药理学意义的螺吡喃，收率良好。这种采用 DBU 的新方案是一种绿色、可回收且价格低廉的催化剂，具有反应条件温和、反应时间短和易于分离产物等优点。这些结构已通过 X 射线分析得到证实。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要
• Application of SBA-Pr-NH2 in one-pot three-component reaction of methylene-carbonyl compounds, acenaphthenequinone, malononitriles and exploration of its antimicrobial activity
  作者：P. Hajiabbasi、G. Mohammadi Ziarani、A. Badiei、A. Abolhasani Soorki

  DOI：10.1007/s13738-014-0454-2

  日期：2015.1

  SBA-Pr-NH2 was found to be a sui table and efficient catalyst for the condensation of acenaphthenequinone, malononitrile/ethylcyanoacetate, and α-methylencarbonyl compounds via a simple, facile, efficient and three-component procedure. The corresponding product was found to have a surprising antimicrobial activity.

  SBA-Pr-NH2被发现是一个合适且高效的催化剂，用于通过简单、方便、高效的三组分程序对芘咯烯醌、马隆腈/乙基氰乙酸酯和α-甲基羧基化合物进行缩合。所得产物显示出惊人的抗菌活性。
• Carbon–SO3H: a novel and recyclable solid acid catalyst for the synthesis of spiro[4H-pyran-3,3′-oxindoles]
  作者：B. Maheshwar Rao、G. Niranjan Reddy、T. Vijaikumar Reddy、B.L.A. Prabhavathi Devi、R.B.N. Prasad、J.S. Yadav、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2013.02.089

  日期：2013.5

  A bioglycerol derived carbon-sulfonic acid is found to catalyze efficiently the three-component one-pot condensation of isatin, malononitrile, and 1,3-dicarbonyls to afford a wide range of spiro[4H-pyran-3,3′-oxindole]derivatives in good yields and selectivity. The use of a recyclable solid acid catalyst makes this method simple, convenient, and cost-effective.

  已发现生物甘油衍生的碳磺酸可有效催化伊斯丁，丙二腈和1,3-二羰基的三组分一锅缩合，从而提供广泛的螺[4H-吡喃-3,3'-羟吲哚]衍生物具有良好的产率和选择性。可循环使用的固体酸催化剂的使用使该方法简单，方便且具有成本效益。
• Ionic liquid catalyzed one-pot synthesis of spiropyran derivatives via three-component reaction in water
  作者：Shuai-Shuai Jin、Mao-Hua Ding、Hong-Yun Guo

  DOI：10.1515/hc-2012-0159

  日期：2013.4.1

  Abstract The ionic liquid [H3N+CH2CH2OH][CH3COO-] (HEAA) catalyzes a three-component, one-pot condensation of malononitrile/ethyl cyanoacetate, 1,3-dicarbonyl compound/enol, and quinone or ninhydrin in water to afford a spiropyran derivative. This method has advantages of mild reaction conditions, short reaction time, and environmental friendliness.

  摘要 离子液体 [H3N+CH2CH2OH][CH3COO-] (HEAA) 催化丙二腈/氰乙酸乙酯、1,3-二羰基化合物/烯醇和醌或茚三酮在水中的三组分一锅缩合反应得到螺吡喃衍生物。该方法具有反应条件温和、反应时间短、环境友好等优点。
• Caspian Isinglass, a versatile and sustainable biocatalyst for domino synthesis of spirooxindoles and spiroacenaphthylenes in water
  作者：Shahrzad Javanshir、Nassim Saghiran Pourshiri、Zahra Dolatkhah、Mohammad Farhadnia

  DOI：10.1007/s00706-016-1779-6

  日期：2017.4

  AbstractIsinglass, derived from swim bladders of Caspian Sea fish and consisting predominantly of protein collagen, was found to be an effective, easily accessible heterogeneous biocatalyst for the synthesis of biologically important functionalized spirooxindoles and spiroacenaphthylenes in water. This facile and efficient one-pot, three-component synthesis route involving isatin or acenaphthenequinone

  摘要被发现来自里海鱼类泳囊的鱼胶主要由蛋白质胶原蛋白组成，是一种有效的，易于获取的异质生物催化剂，可在水中合成生物学上重要的功能化螺氧dol和螺ac。这种简便，有效的一锅三组分合成路线涉及靛红或烯醌，活化的亚甲基试剂和1,3-二羰基化合物，提供了一种新的策略，可以在很短的反应时间内以定量收率产生螺衍生物。 图形概要