3-(2-氯苯基)丙酸甲酯 | 74124-86-0

• 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: 3-(2-氯苯基)丙酸甲酯
• 中文别名: 邻氯苯丙酸甲酯
• 英文名称: methyl 3-(2-chlorophenyl)propanoate
• 英文别名: 3-chlorophenylpropionic acid methyl ester
• CAS: 74124-86-0
• 化学式: C₁₀H₁₁ClO₂
• mdl: MFCD16620959
• 分子量: 198.649
• InChiKey: SKAIVXBBFBJQOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-(2-氯苯基)丙酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-(2-氯苯基)-1-丙醇
  参考文献：
  名称：

  Synthesis of N-Glyoxyl Prolyl and Pipecolyl Amides and Thioesters and Evaluation of Their In Vitro and In Vivo Nerve Regenerative Effects

  摘要：

  The recent discovery that small molecule ligands for the peptidyl-prolyl isomerase (PPIase) FKBP12 possess powerful neuroprotective and neuroregenerative properties in vitro and in vivo suggests therapeutic utility for such compounds in neurodegenerative disease. The neurotrophic effects of these compounds are independent of the immunosuppressive pathways by which drugs such as FK506 and rapamycin operate. Previous work by ourselves and other groups exploring the structure-activity relationships (SAR) of small molecules that mimic only the FKBP binding domain portion of FK506 has focused on esters of proline and pipecolic acid. We have explored amide and thioester analogues of these earlier structures and found that they too are extremely potent in promoting recovery of lesioned dopaminergic pathways in a mouse model of Parkinson's disease. Several compounds were shown to be highly effective upon oral administration after lesioning of the dopaminergic pathway, providing further evidence of the potential clinical utility of a variety of structural classes of FKBP12 ligands.

  DOI：

  10.1021/jm010556c
• 作为产物：
  描述：

  1-(2-氯苯基)乙醇 在 palladium diacetate 、 sodium hydride 、 对甲苯磺酸 、 双(2-二苯基磷苯基)醚 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 130.0 ℃ 、2.5 MPa 条件下， 反应 25.0h， 生成 3-(2-氯苯基)丙酸甲酯
  参考文献：
  名称：

  钯催化仲苄醚的烷氧羰基化

  摘要：

  从仲苄基醚开始合成3-芳基丙酸酯的烷氧基羰基化反应方案，并证明了与已建立的烯烃，醇或芳基卤化物体系具有可比的反应行为。

  DOI：

  10.1002/ejoc.201901592

文献信息

• Cobalt(II)-Catalyzed Alkoxycarbonylation of Aliphatic Amines via C–N Bond Activation
  作者：Chong-Liang Li、Xuan Jiang、Liang-Qiu Lu、Wen-Jing Xiao、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.9b02534

  日期：2019.9.6

  The first cobalt-catalyzed deaminative alkoxycarbonylation reaction was described for the conversion of readily available primary alkyl amines to synthetically versatile esters with moderate to high yields. This transformation shows good functional group compatibility and can serve as a powerful tool for the modification of alkyl amine-containing complex natural products and drug molecules.

  描述了第一个钴催化的脱氨基烷氧羰基化反应，用于以中等到高收率将易于获得的伯烷基胺转化为合成用途的酯。该转化显示出良好的官能团相容性，可以用作修饰含烷基胺的复杂天然产物和药物分子的有力工具。
• Aromatic chlorination of ω-phenylalkylamines and ω-phenylalkylamides in carbon tetrachloride and α,α,α-trifluorotoluene
  作者：Jenny L. O'Connell、Jamie S. Simpson、Paul G. Dumanski、Gregory W. Simpson、Christopher J. Easton

  DOI：10.1039/b605010g

  日期：——

  aromatic chlorination in carbon tetrachloride and alpha,alpha,alpha-trifluorotoluene. These reactions generally show a first-order dependence on the substrate concentration, but not on the amount of chlorine. With carbon tetrachloride, very similar reaction rates are observed with chlorine concentrations ranging from 0.1-1.5 M. In alpha,alpha,alpha-trifluorotoluene, the rates reach a plateau at a chlorine

  简单的烷基苯与氯的芳族卤化反应在乙酸中可顺利进行，但在极性较小的溶剂中效率较低。相反，在乙酸，四氯化碳或α，α，α-三氟甲苯中，ω-苯基烷基胺（如3-苯基丙胺）的氯化反应很容易发生，而在后一种溶剂中，则可得到高比例的邻氯化产物。这些作用归因于N-氯胺作为反应中间体，以及亲电体在分子内的传递。ω-苯基烷基酰胺，例如3-苯基丙酰胺，也很容易在四氯化碳和α，α，α-三氟甲苯中进行芳族氯化反应。这些反应通常表现出对底物浓度的一阶依赖性，但不取决于氯的量。对于四氯化碳，在氯浓度范围为0.1-1.5 M时观察到非常相似的反应速率。在α，α，α-三氟甲苯中，该速率在氯浓度约为0.2 M时达到平稳状态。这些特征表明反应在进行通过中间体的形成，证据表明可能是相应的邻氯亚氨酸盐。不论机理如何，反应都非常迅速，比在乙酸中的类似反应要快，并且比简单烷基苯在四氯化碳中的反应要快三到四个数量级。因此，无需高极性溶剂，
• Metal-Free Catalytic Reduction of α,β-Unsaturated Esters by 1,3,2-Diazaphospholene and Subsequent C–C Coupling with Nitriles
  作者：Che Chang Chong、Bin Rao、Rei Kinjo

  DOI：10.1021/acscatal.7b01338

  日期：2017.9.1

  tautomerizes to saturated esters, while the P–O bond cleavage by HBpin via a formal σ-bond metathesis affords boryl enolate intermediate. The latter could undergo a further coupling reaction with nitriles to form substituted amino diesters or 1,3-imino esters, depending on α,β-unsaturated ester substrates. These catalytic reactions can also be performed in a one-pot manner, illustrating a protocol for metal-free

  1,3,2-二氮杂磷腈1催化α，β-不饱和酯的共轭转移氢化以及1,4-氢硼化。两种方法的起始步骤都包括α，β-不饱和酯的1，4-氢磷酸化，以得到次膦酰基烯醇醚。氨硼烷随后切断了次膦酰基烯醇醚中的P–O键（AB）生成一个互变异构体成饱和酯的烯醇中间体，而HBpin通过正式的σ键复分解通过HB的P–O键裂解，提供了烯醇硼酸酯中间体。取决于α，β-不饱和酯底物，后者可与腈进一步进行偶联反应以形成取代的氨基二酯或1，3-亚氨基酯。这些催化反应也可以一锅法进行，说明了无金属催化C-C键构建的方案。
• Pharmaceutical compositions and method of inhibiting phenylethanolamine
  申请人：SmithKline Corporation

  公开号：US04192888A1

  公开（公告）日：1980-03-11

  Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase using 2-indanamine compounds having 4 and/or 5 substituents.

  制药组合物和使用具有4和/或5取代基的2-茚胺化合物抑制苯乙醇胺N-甲基转移酶的方法。
• Synthesis of<i>N</i>-Substituted Condensed Tetrahydropyridine-Based Enaminones<i>via</i>Palladium-Catalyzed Intramolecular C-N Cross-coupling
  作者：Hana Doušová、Zdeňka Růžičková、Petr Šimůnek

  DOI：10.1002/jhet.3085

  日期：2018.3

  A number of β‐enaminones with secondary amino group (alkyl, cyclopropyl, and aryl) were prepared from corresponding β‐diketones. Two general protocols for their palladium‐catalyzed intramolecular C–N cross‐coupling were established to give corresponding N‐substituted condensed tetrahydropyridines in good yields. The methodology is applicable for a wide variety of structural motifs. The work also extends

  从相应的β-二酮制备了许多具有仲氨基的β-烯胺（烷基，环丙基和芳基）。建立了两种用于钯催化的分子内C–N交叉偶联的通用方案，可以以较高的收率得到相应的N-取代的缩合四氢吡啶。该方法适用于多种结构基序。这项工作还将新近建立的新型钯预催化剂的适用性扩展到新的基质上。