ethyl 5-chloro-2-hydroxy-3-nitrobenzoate | 159323-96-3

• 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: ethyl 5-chloro-2-hydroxy-3-nitrobenzoate
• CAS: 159323-96-3
• 化学式: C₉H₈ClNO₅
• 分子量: 245.619
• InChiKey: UPPGKFOEZDUZBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 储存条件：
  存储条件：2-8°C，干燥。

反应信息

• 作为反应物：
  描述：

  ethyl 5-chloro-2-hydroxy-3-nitrobenzoate 在 palladium on activated charcoal 、 Rh/Al₂O₃ 氢气 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 苯 为溶剂， 25.0~100.0 ℃ 、101.33 kPa 条件下， 反应 83.0h， 生成 Ethyl 4,4-dimethylpyrrolo[2,1-c][1,4]benzoxazine-6-carboxylate
  参考文献：
  名称：

  新的5-HT3（5-羟色胺3）受体拮抗剂。V.吡咯并[2，1-c] [1，4]苯并恶嗪-6-羧酰胺的合成和构效关系。

  摘要：

  本文介绍了结构新颖的杂环羧酰胺的发现，该酰胺是高效的5-HT3（5-羟色胺3）受体拮抗剂。发现吡咯并[2,1-c] [1,4]苯并恶嗪-6-羧酰胺（12和20）对麻醉大鼠的von Bezold-Jarisch反射具有有效的5-HT3受体拮抗剂活性。结构活性研究表明，在芳族环部分的8位上具有小的亲脂性取代基（如氯和甲基）的化合物保留了较高的效价，而具有庞大的取代基的化合物则基本无活性。在4-位的二甲基基团稍微降低了效力。1-氮杂双环[2.2.2]辛-3-胺作为胺部分提供了最有效的活性。在这个系列中，发现20a是最有效的5-HT3受体拮抗剂，

  DOI：

  10.1248/cpb.43.1358
• 作为产物：
  描述：

  5-氯代水杨酸 在 硫酸 、 硝酸 作用下， 以 苯 为溶剂， 反应 5.67h， 生成 ethyl 5-chloro-2-hydroxy-3-nitrobenzoate
  参考文献：
  名称：

  Development of a Phase-Transfer-Catalyzed, [2,3]-Wittig Rearrangement

  摘要：

  An investigation into the use of phase-transfer catalysis for the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds is described. Initial studies focused on identifying viable substrate classes that would undergo selective [2,3]-rearrangement under phase-transfer catalysis. Under certain conditions, the [2,3]-sigmatropic rearrangement of allyloxy carbonyl compounds takes place in the presence of a phase-transfer agent, providing a rare example of a phase-transfer-catalyzed unimolecular reaction. In the course of this investigation, it was found that catalysis is dependent on several variables including base concentration, catalyst structure, and substrate lipophilicity. Preliminary testing of chiral, nonracemic phase-transfer catalysts has shown promising levels of enantioselectivity for future development.

  DOI：

  10.1021/acs.joc.5b01759

文献信息

• BENZOXAZOLE DERIVATIVES AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：Shudo, Koichi

  公开号：EP1134220B1

  公开（公告）日：2004-08-18
• Synthesis and Enzymic Evaluation of Conformationally Defined Carnitine Analogs
  作者：Wayne J. Brouillette、Ashraf Saeed、Ahmed Abuelyaman、Tracy L. Hutchison、Paul E. Wolkowicz、Jeanie B. McMillin

  DOI：10.1021/jo00094a049

  日期：1994.7

  Carnitine (1, 3-hydroxy-4-trimethylammoniobutyrate) is essential as a donor and acceptor of acyl groups in cellular metabolism. The major solution conformation of carnitine about C3-C4 contains the gauche relationship between the trimethylammonium and hydroxy groups, while two of the three low-energy, staggered conformations about C2-C3 are significantly populated. For studies of carnitine's protein binding sites, we designed conformationally defined cyclohexyl carnitine analogs (2-hydroxy-3-trimethylammoniocyclohexanecarboxylate) which all contain the favored carnitine conformation about the C3-C4 bond. Of the four possible diastereomers for these analogs, we synthesized three (2-4) that contain different carnitine conformations about C2-C3. Diastereomers 2 and 3 were prepared via the major diastereomeric products resulting from reduction of ethyl 5-chloro-3-nitrosalicylate (7). Compound 4, which could not be obtained in practical quantities by the above method, was prepared stereoselectively via opening of the epoxide of 3-(benzyloxycarbonylamino)cyclohexene (23) with Et(2)AlCN. Compounds 2-4 were not substrates for pigeon breast carnitine acetyltransferase but were weak, competitive inhibitors with K-i values from 2.9 to 4.1 mM. In contrast, compounds 2 and 4 were not inhibitors of neonatal rat cardiac myocyte CPT-2, while compound 3 was a modest competitive inhibitor (K-i 5.3 mM). These results suggest differences between the carnitine binding sites of CAT and CPT-2.
• Smith; Peirce, American Chemical Journal, 1879, vol. 1, p. 176
  作者：Smith、Peirce

  DOI：——

  日期：——
• A microchip-laser-pumped DFB-polymer-dye laser
  作者：T. Voss、D. Scheel、W. Schade

  DOI：10.1007/s003400100619

  日期：2001.8

  A miniaturized, high repetition rate, picosecond all solid state photo-induced distributed feedback (DFB) polymer-dye laser is described by applying a passively Q-switched and frequency-doubled Cr4+:Nd3+:YAG-microchip laser (pulse width Delta tau = 540ps, repetition rate nu = 3 kHz, pump energy E-pump = 0.15 muJ) as a pump source. A poly-methylmethacrylate film doped with rhodamine B dye serves as active medium. The DFB-laser pulses are temporally and spectrally characterized, and the stability of the thin polymer/dye film at high repetition rates is analyzed. The shortest DFB-laser pulses obtained have a duration of 11 ps. After the emission of 350 000 pulses the intensity of the DFB-laser output has decreased by a factor of two and the pulse duration has increased by a factor of 1.2. For single DFB-laser pulses of 20-ps duration the spectral bandwidth is measured to be Delta lambda = 0.03 nm, which is only 0.005 nm above the calculated Fourier limit assuming a Gaussian profile for the temporal shape of the pulses. Coarse wavelength tuning of the DFB laser between 590 and 619 nm is done by turning the prism. Additionally, a fine tuning of the DFB-polymer-laser wavelength is achieved by changing the temperature of the polymer/dye layer ( d lambda /dT = -0.05 nm/degreesC) in the range from 20 to 40 degreesC.
• US7045516B1
  申请人：——

  公开号：US7045516B1

  公开（公告）日：2006-05-16