prop-2-enyl 4-formylphenylcarbamate | 339221-23-7

• 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: prop-2-enyl 4-formylphenylcarbamate
• 英文别名: allyl 4-formylphenylcarbamate；prop-2-enyl N-(4-formylphenyl)carbamate
• CAS: 339221-23-7
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: UUWPNTQMTRPOIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  119 °C
• 沸点：
  291.1±33.0 °C(Predicted)
• 密度：
  1.216±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲氧基三甲基硅烷 、 prop-2-enyl 4-formylphenylcarbamate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到allyl 4-(dimethoxymethyl)phenylcarbamate
  参考文献：
  名称：

  A Structurally Simple Self-Immolative Reagent That Provides Three Distinct, Simultaneous Responses per Detection Event

  摘要：

  A general design is presented for a stimulus-responsive small molecule that is capable of responding to a specific applied chemical or physical signal by releasing two different types of pendant small molecules and a colorimetric indicator simultaneously. A key aspect of this design is the ease with which these reagents are prepared: typically, only four synthetic steps are required. Moreover, the modular construction strategy provides access to stimuli-responsive reagents that are capable of (i) responding to a variety of applied signals and (ii) releasing a number of different small molecules that contain primary alcohols, secondary alcohols, or phenols. These stimuli-responsive reagents are stable under physiological conditions (neither hydrolysis nor thermal degradation of the reagent occurs in significant quantity), and when they are exposed to the appropriate applied signal, they release both pendant small molecules and the colorimetric indicator completely within hours. Finally, unlike other functional groups, such as carbonates, that are used to connect alcohol-bearing molecules to controlled-release reagents, the linkage described in this article increases in hydrolytic stability (rather than decreases) as the plc of the pendant alcohol decreases.

  DOI：

  10.1021/jo2018763
• 作为产物：
  描述：

  (4-hydroxymethyl-phenyl)-carbamic acid allyl ester 在 戴斯-马丁氧化剂 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 prop-2-enyl 4-formylphenylcarbamate
  参考文献：
  名称：

  Indole nitriles

  摘要：

  式(I)的化合物，其中m、n、R1、R2、R3、R4、R5和R6如本文所述，以及制备这些化合物的方法和利用这些化合物治疗由Cathepsin K介导的疾病或症状的方法。

  公开号：

  US20040077646A1

文献信息

• Heteroaryl nitriles
  申请人：——

  公开号：US20030212097A1

  公开（公告）日：2003-11-13

  The present invention relates to compound of formula (I) 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 and n are as defined in the description and claims and pharmaceutically acceptable salts and/or pharmaceutically acceptable esters thereof. The compounds are useful for the treatment of diseases which are associated with cysteine proteases such as osteoporosis, osteoarthritis, rheumatoid arthritis, tumor metastasis, glomerulonephritis, atherosclerosis, myocardial infarction, angina pectoris, instable angina pectoris, stroke, plaque rupture, transient ischemic attacks, amaurosis fugax, peripheral arterial occlusive disease, restenosis after angioplasty and stent placement, abdominal aortic aneurysm formation, inflammation, autoimmune disease, malaria, ocular fundus tissue cytopathy and respiratory disease.

  本发明涉及以下式（I）的化合物 1 其中R 1 ，R 2 ，R 3 ，R 4 ，R 5 和n如描述和索赔中所定义，并且其药学上可接受的盐和/或药学上可接受的酯。这些化合物可用于治疗与半胱氨酸蛋白酶相关的疾病，如骨质疏松症、骨关节炎、类风湿关节炎、肿瘤转移、肾小球肾炎、动脉粥样硬化、心肌梗死、心绞痛、不稳定性心绞痛、中风、斑块破裂、短暂性缺血发作、短暂性视网膜动脉阻塞、外周动脉闭塞症、血管成形术后再狭窄和支架植入术后再狭窄、腹主动脉瘤形成、炎症、自身免疫疾病、疟疾、眼底组织细胞病变和呼吸道疾病。
• Iodine(V) Reagents in Organic Synthesis. Part 4. <i>o</i>-Iodoxybenzoic Acid as a Chemospecific Tool for Single Electron Transfer-Based Oxidation Processes
  作者：K. C. Nicolaou、T. Montagnon、P. S. Baran、Y.-L. Zhong

  DOI：10.1021/ja012127+

  日期：2002.3.1

  o-Iodoxybenzoic acid (IBX), a readily available hypervalent iodine(V) reagent, was found to be highly effective in carrying out oxidations adjacent to carbonyl functionalities (to form alpha,beta-unsaturated carbonyl compounds) and at benzylic and related carbon centers (to form conjugated aromatic carbonyl systems). Mechanistic investigations led to the conclusion that these new reactions are initiated

  o-碘氧基苯甲酸 (IBX) 是一种容易获得的高价碘 (V) 试剂，被发现在与羰基官能团相邻（形成 α、β-不饱和羰基化合物）以及苄基和相关碳中心进行氧化方面非常有效（形成共轭芳香羰基体系）。机理研究得出的结论是，这些新反应是由从底物到 IBX 的单电子转移 (SET) 引发的，以形成自由基阳离子，该阳离子进一步反应以产生最终产物。反应条件的微调允许在多功能底物内进行显着的选择性转化，将该试剂的状态提升为非常有用的化学选择性氧化剂。
• Propylphosphonic Anhydride (T3P®)-Mediated One-Pot Rearrangement of Carboxylic Acids to Carbamates
  作者：John Augustine、Agnes Bombrun、Ashis Mandal、Padma Alagarsamy、Rajendra Atta、Panneer Selvam

  DOI：10.1055/s-0030-1259964

  日期：2011.5

  A simple one-pot conversion of carboxylic acids to carbamates is achieved by propylphosphonic anhydride (T3P®) in combination with azidotrimethylsilane and an alcohol via the Curtius­ rearrangement. Besides diverse primary to tertiary alcohols, the reaction tolerated a wide scope of aromatic, heterocyclic, and ­aliphatic carboxylic acids which underwent rearrangement in ­excellent yields. propylphosphonic

  的羧酸的简单的一锅转变成氨基甲酸酯通过丙基膦酸酐（T3P实现®与azidotrimethylsilane组合），并通过Curtius重排的醇。除了多样化的伯醇至叔醇外，该反应还耐受各种芳族，杂环和脂肪族羧酸，这些羧酸经过重排后具有极高的收率。 丙基膦酸酐-Curtius重排-氨基甲酸酯-肽偶联剂-叠氮基三甲基硅烷
• Selective Oxidation at Carbon Adjacent to Aromatic Systems with IBX
  作者：K. C. Nicolaou,*、Phil S. Baran、Yong-Li Zhong

  DOI：10.1021/ja004218x

  日期：2001.4.1

  oxidation of benzylic positions is quite general and proceeds efficiently in fluorobenzene/DMSO (2:1) or DMSO at 80 -90 °C. The reaction is not affected by the presence of water (entry 3), o-substituents (entries 4, 9, 11, 14, 17), or the presence of halogens (entries 5, 6). Over-oxidation to the corresponding carboxylic acid was not observed even in the presence of electron-rich substrates (entry 7). n-Butylbenzene

  接收日期 2000 年 12 月 5 日 最近这些实验室报告了许多基于高碘烷试剂 DMP 和 IBX 反应性的新合成技术。1 这些反应包括 IBX 诱导的不饱和苯胺的环化（图 1A），1b 其单电子转移（SET）机制最近被阐明，2 以及在羰基旁边引入不饱和基团，1d 现在也被认为是进行类推，通过 SET 机制（图 1B）。基于这些机械原理，我们假设 IBX 可以通过 SET 机制氧化苄基位置，如图 1C 所示。如果有选择性且易于控制，鉴于潜在底物的易得性和稳定性以及相应氧化产物的广泛用途，这种方法可能是有机合成中的一种有价值的工具。4 在此，我们报告了这种过程的实现、范围和一般性，并证明了基于简单修改反应条件的 IBX 介导过程的显着化学选择性。如表 1 所示，IBX 诱导的苄基位置氧化非常普遍，并且在 80 -90 °C 的氟苯/DMSO (2:1) 或 DMSO 中有效进行。该反应不受水（条目
• SUBSTITUTED 2-AMINO-CYCLOALKANECARBOXAMIDES AND THEIR USE AS CYSTEINE PROTEASE INHIBITORS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1453801A1

  公开（公告）日：2004-09-08