4-羟基甲基苯甲酸叔丁酯 | 143726-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-羟基甲基苯甲酸叔丁酯
• 英文名称: tert-butyl 4-(hydroxymethyl)benzoate
• CAS: 143726-85-6
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD04973449
• 分子量: 208.257
• InChiKey: MGMZECMXYCZYSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温下应存放在干燥密封的环境中。

反应信息

• 作为反应物：
  描述：

  4-羟基甲基苯甲酸叔丁酯 在 N,N-二甲基甲酰胺 4-二甲氨基吡啶 、 草酰氯 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 3-[4'-(tert-butyloxycarbonyl)benzyloxycarbonyl]phenylacetic chloride
  参考文献：
  名称：

  Design, Synthesis, and Proposed Active Site Binding Analysis of Monocyclic 2-Azetidinone Inhibitors of Prostate Specific Antigen

  摘要：

  A homology derived molecular model of prostate specific antigen (PSA) was created and refined. The active site region was investigated for specific interacting functionality and a binding model postulated for the novel 2-azetidinone acyl enzyme inhibitor 1 (IC50 = 8.98 +/- 0.90 muM) which was used as a lead compound in this study. A single low energy conformation structure II (Figure 2) was adopted as most likely to represent binding after minimization and dynamics calculations. Systematic analysis of the binding importance of all three side chains appended to the 2-azetidinone was conducted by the synthesis of several analogues. A proposed salt bridge to Lys-145 with 4 (IC50 = 5.84 +/- 0.92 muM) gave improved inhibition, but generally the binding of the N-1 side chain in a specific secondary aromatic binding site did not tolerate much structural alteration. A hydrophobic interaction of the C-4 side chain afforded inhibitor 6 (IC50 = 1.43 +/- 0.19 muM), and polar functionality could also be added in a proposed interaction with Gln-166 in 5 (IC50 = 1.34 +/- 0.05 muM). Reversal of the C-4 ester connectivity furnished inhibitors 7 (IC50 = 1 59 +/- 0 15 muM), 11 (IC50 = 3.08 +/- 0.41 muM), and 13 (IC50 = 2.19 +/- 0.36 muM) which were perceived to bind to PSA by a rotation of 180 degrees relative to the C-4 ester of normal connectivity. Incorporation of hydroxyl functionality into the C-3 side chain provided 16 (IC50 = 348 +/- 50 nM) with the greatest increase in PSA inhibition by a single modification. Multiple copy simultaneous search (MCSS) analysis of the PSA active site further supported our model and suggested that 18 would bind strongly. Asymmetric synthesis yielded 18 (IC50 = 226 +/- 10 nM) as the most potent inhibitor of PSA reported to date. It is concluded that our design approach has been successful in developing PSA inhibitors and could also be applied to the inhibition of other enzymes, especially in the absence of crystallographic information.

  DOI：

  10.1021/jm000145g
• 作为产物：
  描述：

  4-(叔丁氧羰基)苯甲 酸 在 tetrabutylammonium borohydride 作用下， 反应 18.0h， 以75%的产率得到4-羟基甲基苯甲酸叔丁酯
  参考文献：
  名称：

  Synthesis and biological activity of optimized belactosin C congeners

  摘要：

  对天然产物贝乳糖素 A 和 C 及其更稳定的酰化衍生物的成功生化研究证明它们是强大的蛋白酶体抑制剂，因此是作为药理学相关活性化合物的潜在候选者。为了详细了解它们的结构-生物活性关系并找到提高其生物活性的方法，合成并测试了四种新的修饰贝乳素同系物。其中一种（化合物 6）被证明是比已知的蛋白酶体抑制剂 MG132 更有效的 HeLa 细胞抑制剂。

  DOI：

  10.1039/c1ob05661a

文献信息

• Protease inhibitors
  申请人：——

  公开号：US20020049316A1

  公开（公告）日：2002-04-25

  The present invention provides compounds of formula (I) which inhibit proteases, including cathepsin K, pharmaceutical compositions of such compounds, and methods for treating diseases of excessive bone loss or cartilage or matrix degradation, including osteoporosis; gingival disease including gingivitis and periodontitis; arthritis, more specifically, osteoarthritis and rheumatoid arthritis; Paget's disease; hypercalcemia or malignancy; and metabolic bone disease therewith.

  本发明提供了一种公式（I）的化合物，其抑制蛋白酶，包括卡特普辛K，以及这些化合物的药物组合物，以及治疗骨量过度流失或软骨或基质降解疾病的方法，包括骨质疏松症；牙龈疾病，包括牙龈炎和牙周炎；关节炎，更具体地说是骨关节炎和类风湿关节炎；帕吉特病；高钙血症或恶性肿瘤；以及代谢性骨病。
• Nickel/N-Heterocyclic Carbene Complex-Catalyzed Enantioselective Redox-Neutral Coupling of Benzyl Alcohols and Alkynes to Allylic Alcohols
  作者：Yuan Cai、Jia-Wen Zhang、Feng Li、Jia-Ming Liu、Shi-Liang Shi

  DOI：10.1021/acscatal.8b04198

  日期：2019.1.4

  The nickel-catalyzed enantioselective redox-neutral coupling of alcohols and alkynes to access chiral allylic alcohols is reported. The reaction proceeds via a hydrogen transfer process under ambient temperature, converting abundant feedstock alcohols and alkynes to chiral allylic alcohols with high stereoselectivities in one chemical step. Key to the success of this process was the development of

  据报道，醇和炔烃的镍催化对映选择性氧化还原-中性偶合反应可得到手性烯丙基醇。反应在环境温度下通过氢转移过程进行，在一个化学步骤中将丰富的原料醇和炔烃转化为具有高立体选择性的手性烯丙基醇。该方法成功的关键是开发了庞大的手性N-杂环卡宾（R，R，R，R，R）-SIPE（SIPr的手性版本）作为镍的配体。值得注意的是，我们发现利用P（OPh）3作为镍的二级配体对于抑制产物的异构化至关重要。
• RADIATION-SENSITIVE RESIN COMPOSITION, RESIST PATTERN-FORMING METHOD, COMPOUND AND METHOD OF GENERATING ACID
  申请人：JSR CORPORATION

  公开号：US20200341376A1

  公开（公告）日：2020-10-29

  A radiation-sensitive resin composition contains: a polymer that includes a structural unit including an acid-labile group; and a radiation-sensitive acid generating agent. The radiation-sensitive acid generating agent includes a sulfonate anion and a radiation-sensitive cation. The sulfonate anion includes two or more rings, and an iodine atom and a monovalent group having 0 to 10 carbon atoms which includes at least one of an oxygen atom and a nitrogen atom bond to at least one of the two or more rings. The ring is preferably an aromatic ring. The radiation-sensitive acid generating agent is preferably a compound represented by formula (1). In the formula (1), A 1 represents a group obtained from a compound which includes a ring having 3 to 20 ring atoms by removing (p+q+r+1) hydrogen atoms on the ring.

  一种辐射敏感树脂组合物包含：包括含有酸敏感基团的结构单元的聚合物；和辐射敏感酸发生剂。辐射敏感酸发生剂包括磺酸根离子和辐射敏感阳离子。磺酸根离子包括两个或两个以上的环，以及一个碘原子和一个含有0至10个碳原子的一价基团，其中该基团至少包括一个氧原子和一个氮原子，与两个或两个以上的环中的至少一个结合。环最好是芳香环。辐射敏感酸发生剂最好是由式（1）表示的化合物。在式（1）中，A1表示通过去除环上（p+q+r+1）个氢原子而获得的由含有3至20个环原子的环的化合物得到的基团。
• Synthesis of Tetrasubstituted Thieno[3,2-<i>b</i>]pyridin-5(4<i>H</i>)-one Derivatives as a Heterocyclic Scaffold for Multisite-specific Fluorous Fluorescent Tagging and Fluorous Solid-Phase Extraction
  作者：Moon-Kook Jeon、Su-Jin Yi、Seung Uk Son

  DOI：10.1002/bkcs.10840

  日期：2016.8

  Tetrasubstituted thieno[3,2‐b]pyridin‐5(4H)‐one derivatives were selected as a highly functionalized heterocyclic scaffold for a multisite‐specific tagging process utilizing a previously devised fluorous fluorescent tag system. A suitable synthetic method was established for the 7‐alkoxy‐2,4,6‐trisubstituted‐thieno[3,2‐b]pyridin‐5(4H)‐one derivatives, and incorporating t‐butoxycarbonyl‐functionalized

  使用先前设计的荧光标记系统，选择了四取代的噻吩并[3,2 - b ]吡啶5-5 （4 H）-one衍生物作为高度功能化的杂环支架，用于多位点特异性标记过程。建立了合适的合成方法用于7-烷氧基-2,4,6-三取代-噻吩并[3,2 - b ]吡啶5-5 （4 H）-one衍生物，并将叔丁氧羰基官能化的结构单元并入反应序列产生的前体可用于标记过程。经过一系列反应，包括t- Bu脱保护/ N，通过氟固相萃取有助于标记的目标化合物的纯化-羟基琥珀酰亚胺酯的形成/酰胺化。
• [EN] PYRAZOLE DERIVATIVES FOR THE TREATMENT OF CYSTIC FIBROSIS<br/>[FR] NOUVEAUX DÉRIVÉS DE PYRAZOLE POUR LE TRAITEMENT DE LA FIBROSE KYSTIQUE
  申请人：FONDAZIONE ST ITALIANO TECNOLOGIA

  公开号：WO2018167695A1

  公开（公告）日：2018-09-20

  The present invention relates to compounds of Formula (I) or pharmaceutically acceptable salts or solvates thereof. It further discloses a pharmaceutical composition comprising the compounds of Formula (I) and their uses, in particular to modulate CFTR protein or ABC protein activities.

  本发明涉及式（I）化合物或其药用可接受的盐或溶剂。还披露了包括式（I）化合物的药物组合物及其用途，特别是用于调节CFTR蛋白或ABC蛋白的活性。