2-(1,2-苯异噁唑-3-基)乙酸甲酯 | 59899-89-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 中文名称: 2-(1,2-苯异噁唑-3-基)乙酸甲酯
• 中文别名: 2-(1,2-苯并异恶唑-3-基)乙酸甲酯
• 英文名称: 1,2-benzisoxazol-3-ylacetic acid methyl ester
• 英文别名: 1,2-benzisoxazole-3-acetic acid methyl ester；methyl 2-(benzo[d]isoxazol-3-yl)acetate；methyl 2-(1,2-benzoxazol-3-yl)acetate；methyl 1,2-benzisoxazol-3-yl acetate；methyl 1,2-benzisoxazol-3-ylacetate；methyl 1,2-benzisoxazole-3-acetate；Methyl 2-(1,2-benzisoxazol-3-yl)acetate
• CAS: 59899-89-7
• 化学式: C₁₀H₉NO₃
• mdl: MFCD04117784
• 分子量: 191.186
• InChiKey: VKNXYAQLRDOEFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,2-苯异噁唑-3-基)乙酸甲酯 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 N-[2-(1,2-benzoxazol-3-yl)ethoxy-(dimethylamino)phosphoryl]-N-methylmethanamine
  参考文献：
  名称：

  1,2-Benzisoxazole Phosphorodiamidates as Novel Anticancer Prodrugs Requiring Bioreductive Activation

  摘要：

  Several 1,2-benzisoxazole phosphorodiamidates have been designed as prodrugs of phosphoramide mustard requiring bioreductive activation. Enzymatic reduction of 1,2-benziosoxazole moiety is expected to result in the formation of imine intermediate due to the cleavage of the N-O bond. The imine should then be spontaneously hydrolyzed to a ketone metabolite, thereby facilitating base-catalyzed beta-elimination of cytotoxic phosphoramide mustard. As expected, the proposed prodrugs 4, 9, and 12 were at least 3-5-fold more potent cytotoxins than control compounds 5 and 15, which lack in the phosphoramide mustard group. Upon incubation with phenobarb-induced rat liver S-9 fraction, compounds 4, 9, and 12 underwent extensive NADPH-dependent metabolism with concomitant generation of alkylating activity under both hypoxic and oxic conditions. Corresponding ketone metabolites were detected for 9 and 15. NADPH-dependent bioreduction of 15 to its ketone metabolite 16 was located in the microsomal fraction and inhibited by SKF-525A and pCMBA. Compared with phenobarb-induced rat liver microsomal fraction, incubation of 15 with rat or human P450 reductase microsomes showed moderate generation of 16. Microsomal cytochrome P450 and/or P450 reductase appear to be involved in the reductive metabolism of 1,2-benzisoxazole moiety under hypoxic as well as oxic conditions.

  DOI：

  10.1021/jm020581y
• 作为产物：
  描述：

  methyl (1,2-benzisoxazol-3-yl)(phenylthio)acetate 在 sodium periodate 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 22.0h， 生成 2-(1,2-苯异噁唑-3-基)乙酸甲酯
  参考文献：
  名称：

  Ueda, Shozo; Naruto, Shunsuke; Yoshida, Toyokichi, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1013 - 1022

  摘要：

  DOI：

文献信息

• [EN] NEW SOMATOSTATIN RECEPTOR SUBTYPE 4 (SSTR4) AGONISTS<br/>[FR] NOUVEAUX AGONISTES DU RÉCEPTEUR DE SOMATOSTATINE DE SOUS-TYPE 4 (SSTR4)
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014184275A1

  公开（公告）日：2014-11-20

  The invention relates to 3-aza-bicyclo[3.1.0]hexane-6-carboxylic acid amide derivatives of general formula (I), which are agonists of somatostatin receptor subtype 4 (SSTR4), useful for preventing or treating medical disorders related to SSTR4. In addition, the invention relates to processes for preparing pharmaceutical compositions as well as processes for manufacture of the compounds according to the invention.

  这项发明涉及一般式(I)的3-aza-双环[3.1.0]己烷-6-羧酸酰胺衍生物，它们是生长抑素受体亚型4（SSTR4）的激动剂，用于预防或治疗与SSTR4相关的医学疾病。此外，该发明涉及制备药物组合物的方法，以及根据该发明制备化合物的方法。
• Green Esterification of Carboxylic Acids Promoted by <i>tert</i> ‐Butyl Nitrite
  作者：Yonggao Zheng、Yanwei Zhao、Suyan Tao、Xingxing Li、Xionglve Cheng、Gangzhong Jiang、Xiaobing Wan

  DOI：10.1002/ejoc.202100326

  日期：2021.5.14

  TBN‐catalyzed green esterification of carboxylic acids has been developed, which features a broad range of substrates and excellent functional groups tolerance. The mechanistic study confirmed that the nitrous acid formed in situ in the system is the actual catalyst for this transformation.

  已经开发了TBN催化的羧酸绿色酯化反应，它具有多种底物和出色的官能团耐受性。机理研究证实，在系统中原位形成的亚硝酸是该转化的实际催化剂。
• Synthesis and spasmolytic activity of aminoalkyl 2-substituted-2-(1,2-benzisoxazol-3-yl)acetates.
  作者：SHUNSUKE NARUTO、SHOZO UEDA、TOYOKICHI YOSHIDA、HIROYUKI MIZUTA、KATSUYOSHI KAWASHIMA、TOSHIAKI KADOKAWA

  DOI：10.1248/cpb.35.2095

  日期：——

  Several aminoalkyl esters of 2- (1, 2-benzisoxazol-3-yl) -2-cyclohexylacetic acid, 1- (1, 2-benzisoxazol-3-yl) -1-cyclopentanecarboxylic acid, and 1- (1, 2-benzisoxazol-3-yl) -1-cyclohexanecarboxylic acid and their quaternary ammonium salts were synthesized. The anticholinergic (anti-Ach) and musculotropic (anti-KCl) activities of these compounds were examined. Among them, 3- (N, N-diethylamino) -propyl 2- (1, 2-benzisoxazol-3-yl) -2-cyclohexylacetate (8b) showed potent anti-Ach and anti-KCl activities.

  若干2-（1,2-苯并异噁唑-3-基）-2-环己基乙酸、1-（1,2-苯并异噁唑-3-基）-1-环戊烷羧酸和1-（1,2-苯并异噁唑-3-基）-1-环己烷羧酸的氨基烷基酯及其季铵盐被合成。这些化合物的抗胆碱能（抗乙酰胆碱）和肌肉亲和性（抗氯化钾）活性得到了检测。其中，3-（N,N-二乙基氨基）-丙基 2-（1,2-苯并异噁唑-3-基）-2-环己基乙酸酯（8b）表现出强效的抗乙酰胆碱和抗氯化钾活性。
• Enantioselective Nickel-Catalyzed Michael Additions of Azaarylacetates and Acetamides to Nitroalkenes
  作者：Charlene Fallan、Hon Wai Lam

  DOI：10.1002/chem.201202093

  日期：2012.9.3

  Put a nickel in it: Azaarylacetates and acetamides, which have been neglected as substrates in catalytic asymmetric synthesis, undergo highly enantioselective Michael additions to nitroalkenes in the presence of a chiral nickel(II)‐bis(diamine) complex (see scheme; Bn=benzyl, MS=molecular sieves). This process is tolerant of a wide variety of azaarenes in the pronucleophile.

  在其中放镍：在手性镍（II）-双（二胺）配合物的存在下，氮杂芳基乙酸酯和乙酰胺在催化不对称合成中被忽略为底物，对硝基烯烃进行高度对映选择性的迈克尔加成反应（见方案； Bn =苄基，MS =分子筛）。该过程可耐受亲核试剂中的多种氮杂氮杂。
• 一种羧酸酯化合物的制备方法
  申请人：苏州大学

  公开号：CN112552171B

  公开（公告）日：2022-04-26

  本发明涉及一种羧酸酯化合物的制备方法：在亚硝酸酯的催化下，羧酸与甲醇在空气下反应，得到酯化合物。本发明的制备方法具有原料来源丰富、催化剂廉价易得、反应条件温和且操作简便等优点，可高收率的修饰一系列脂肪羧酸，特别要说明的是，传统的酯化方法一般不适合药物分子的酯化。利用本方法，可以对一系列已知药物分子进行修饰，从而为发现新的药物分子提供捷径。