5-methoxy-1-oxo-indan-2-carbonitrile | 873422-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-methoxy-1-oxo-indan-2-carbonitrile
• 英文别名: (+/-)-5-Methoxy-1-oxo-indan-carbonsaeure-(2)-nitril；2,3-Dihydro-5-methoxy-1-oxo-1h-indene-2-carbonitrile；6-methoxy-3-oxo-1,2-dihydroindene-2-carbonitrile
• CAS: 873422-55-0
• 化学式: C₁₁H₉NO₂
• mdl: MFCD11219406
• 分子量: 187.198
• InChiKey: CWYNVXRBLXQRCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methoxy-1-oxo-indan-2-carbonitrile 在 氢氧化钾 作用下， 生成 3-(2-Carboxy-5-methoxy-phenyl)-propionsaeure
  参考文献：
  名称：

  A Glucomannan and Chitosan Fiber Supplement Decreases Plasma Cholesterol and Increases Cholesterol Excretion in Overweight Normocholesterolemic Humans

  摘要：

  Objective: Both chitosan and glucomannan have demonstrated hypocholesterolemic effects. A recent study in rats indicates that the combination of the two is also a potent hypocholesterolemic agent that increases fecal fat excretion. The objective of the present study was to determine the hypocholesterolemic effect of a supplement containing equal amounts of chitosan and glucomannan on blood lipid concentrations and fecal excretion of fat, neutral sterols and bile acids.Methods: Twenty-one overweight normocholesterolemic subjects (I I males and 10 females) were fed 2.4 g/day of a supplement containing equal amounts of chitosan and glucomannan. Prior to taking the supplement (initial period) and after 28 days (final period), blood was drawn for measurement of serum lipids and a three-day fecal sample collected for determination of fat, neutral sterol and bile acid excretion. Subjects maintained their normal dietary and activity patterns during the study.Results: Caloric intake and intake of fat and dietary fiber (excluding the supplement) did not differ between the initial and final periods. Serum total, HDL and LDL cholesterol concentrations were significantly lower (P < 0.05) in the final period compared to the initial period. Serum triacylglycerol concentration did not change between periods. There was a trend towards greater fecal excretion of neutral sterols and bile acids (p = 0.13 and 0.16, respectively) in the final period. However. fecal fat excretion did not differ between periods.Conclusions: Serum cholesterol reduction by a chitosan/glucomannan supplement is likely mediated by increased fecal steroid excretion and is not linked to fat excretion.

  DOI：

  10.1080/07315724.2002.10719246
• 作为产物：
  描述：

  氰化钠 、 alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 作用下， 生成 5-methoxy-1-oxo-indan-2-carbonitrile
  参考文献：
  名称：

  A Glucomannan and Chitosan Fiber Supplement Decreases Plasma Cholesterol and Increases Cholesterol Excretion in Overweight Normocholesterolemic Humans

  摘要：

  Objective: Both chitosan and glucomannan have demonstrated hypocholesterolemic effects. A recent study in rats indicates that the combination of the two is also a potent hypocholesterolemic agent that increases fecal fat excretion. The objective of the present study was to determine the hypocholesterolemic effect of a supplement containing equal amounts of chitosan and glucomannan on blood lipid concentrations and fecal excretion of fat, neutral sterols and bile acids.Methods: Twenty-one overweight normocholesterolemic subjects (I I males and 10 females) were fed 2.4 g/day of a supplement containing equal amounts of chitosan and glucomannan. Prior to taking the supplement (initial period) and after 28 days (final period), blood was drawn for measurement of serum lipids and a three-day fecal sample collected for determination of fat, neutral sterol and bile acid excretion. Subjects maintained their normal dietary and activity patterns during the study.Results: Caloric intake and intake of fat and dietary fiber (excluding the supplement) did not differ between the initial and final periods. Serum total, HDL and LDL cholesterol concentrations were significantly lower (P < 0.05) in the final period compared to the initial period. Serum triacylglycerol concentration did not change between periods. There was a trend towards greater fecal excretion of neutral sterols and bile acids (p = 0.13 and 0.16, respectively) in the final period. However. fecal fat excretion did not differ between periods.Conclusions: Serum cholesterol reduction by a chitosan/glucomannan supplement is likely mediated by increased fecal steroid excretion and is not linked to fat excretion.

  DOI：

  10.1080/07315724.2002.10719246

文献信息

• Direct Access to N-Unprotected α- and/or β-Tetrasubstituted Amino Acid Esters via Direct Catalytic Mannich-Type Reactions Using N-Unprotected Trifluoromethyl Ketimines
  作者：Masanao Sawa、Kazuhiro Morisaki、Yuta Kondo、Hiroyuki Morimoto、Takashi Ohshima

  DOI：10.1002/chem.201703516

  日期：2017.12.1

  bond‐forming reactions using Mannich‐type reactions as a model case. We demonstrate that Lewis acid catalysis was effective for promoting reactions with various N‐unprotected trifluoromethyl ketimines, and thiourea organocatalysis was effective for promoting highly enantioselective reactions with various carbonyl nucleophiles, providing direct access to various N‐unprotected α‐ and/or β‐tetrasubstituted

  在N-未保护的酮亚胺中直接催化C-C键形成的加成是合成N-未保护的四取代胺的一种有效而直接的方法，它消除了先前的保护/脱保护步骤，并使产物易于转化。尽管有其优点，但N保护基的酮亚胺在C键形成反应中有困难，与N保护基相比，仅报道了有限数量的反应和底物。在此我们报道，使用曼尼希型反应作为模型案例，N-未保护的三氟甲基酮亚胺对C-C键形成反应有效。我们证明了路易斯酸催化可有效地促进与各种N-未保护的三氟甲基酮亚胺的反应，硫脲有机催化可有效促进与各种羰基亲核试剂的高度对映选择性反应，可直接获得各种N-未保护的α-和/或β-四取代的氨基酸酯。此外，首次以高度对映和非对映选择性的方式直接构建了邻位四取代手性碳立体中心。这些结果证明了N-未保护的酮亚胺作为适用于许多其他加成反应的底物的潜力。
• Enantio- and Diastereoselective Mannich-Type Reactions of α-Cyano Ketones with<i>N</i>-Boc Aldimines Catalyzed by Chiral Bifunctional Urea
  作者：Ju Hee Lee、Dae Young Kim

  DOI：10.1002/adsc.200900268

  日期：2009.8

  The catalytic enantioselective electrophilic Mannich-type reaction promoted by chiral bifunctional organocatalysts is described. The treatment of α-cyano ketones with N-Boc-aldimines under mild reaction conditions afforded the corresponding β-amino-α-cyano ketones with excellent diastereoselectivities (up to syn/anti=100/0), and excellent enantioselectivities (up to 99% ee).

  描述了由手性双官能有机催化剂促进的催化对映选择性亲电曼尼希型反应。在温和的反应条件下，用N -Boc-醛亚胺处理α-氰基酮，得到相应的β-氨基-α-氰基酮，具有非对映选择性（高达syn / anti = 100/0）和出色的对映选择性（高达99） ％ee）。
• Enantio- and diastereoselective Michael addition reactions of α-cyanoketones to nitroalkenes catalyzed by binaphthyl-derived organocatalyst
  作者：Hyun Joo Lee、Saet Byeol Woo、Dae Young Kim

  DOI：10.1016/j.tetlet.2012.04.095

  日期：2012.6

  The catalytic enantioselective and diastereoselective Michael addition reactions promoted by chiral bifunctional organocatalysts are described. The treatment of alpha-cyanoketones with nitroalkenes under mild reaction conditions afforded the corresponding gamma-niro alpha-cyanoketones with excellent diastereoselectivities (up to syn/anti >99/1) and excellent enantioselectivities (up to 99% ee). (C) 2012 Elsevier Ltd. All rights reserved.
• VERFAHREN ZUR HERSTELLUNG VON 2-CYANOINDAN-1-ONEN
  申请人：Bayer Aktiengesellschaft

  公开号：EP1007507B1

  公开（公告）日：2002-11-06
• US6355827B1
  申请人：——

  公开号：US6355827B1

  公开（公告）日：2002-03-12