2-氯-3-苯基丙-2-烯酸 | 705-54-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 2-氯-3-苯基丙-2-烯酸
• 英文名称: (Z)-α-chlorocinnamic acid
• 英文别名: α-chlorocinnamic acid；(2Z)-2-Chloro-3-phenylacrylic acid；(Z)-2-chloro-3-phenylprop-2-enoic acid
• CAS: 705-54-4
• 化学式: C₉H₇ClO₂
• 分子量: 182.606
• InChiKey: IWZNLKUVIIFUOG-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-3-苯基丙-2-烯酸 在 硫酸 、 硝酸 作用下， 生成 (Z)-ethyl 2-chloro-3-(4-nitrophenyl)-2-propenoate
  参考文献：
  名称：

  Pfeiffer, Chemische Berichte, 1914, vol. 47, p. 1768

  摘要：

  DOI：
• 作为产物：
  描述：

  2-chloro-3-hydroxy-3-phenyl-propionic acid 在 sodium acetate 、 乙酸酐 作用下， 生成 2-氯-3-苯基丙-2-烯酸
  参考文献：
  名称：

  Forrer, Chemische Berichte, 1883, vol. 16, p. 854

  摘要：

  DOI：

文献信息

• Phenylalanine derivatives enhancing intestinal absorption of insulin in mice.
  作者：YUSUKE AMINO、KAZUHIRO KAWADA、KOJI TOI、IZUMI KUMASHIRO、KOJI FUKUSHIMA

  DOI：10.1248/cpb.36.4426

  日期：——

  The adjuvant effect of N-acyl-L-and D-phenylalanine derivatives on intestinal absorption of insulin was investigated in normal mice. The correlation between the chemical structural properties of the N-acyl moiety and the absorption-promoting activity was estimated from the glucose concentrations and the insulin levels in the blood of mice after oral combined administration of insulin and adjuvant. The chemical structural properties of N-acyl-phenylalanine derivatives necessary for adjuvant effect on intestinal absorption of insulin were as follows. 1. An aromatic ring is present, separated by two atoms from the acyl carbonyl group. 2. Either of X or Y is oxygen or X-Y is a double bond in Fig.2. 3. The N-acyl moiety has small hydrophobic substituents, such as F, Cl, or Me at Rα, Rβ, Rη and has an appropriate hydrophilic-hydrophobic balance of the overall molecule. The use of these agents to enhance insulin absorption offers the possibility of a new approach to oral insulin therapy.

  研究了N-酰基-L-和D-苯丙氨酸衍生物对正常小鼠胰岛素肠道吸收的辅助效应。根据小鼠口服胰岛素和辅料联合给药后的血糖浓度和胰岛素水平，推测了N-酰基部分的化学结构性质与促吸收活性之间的相关性。N-酰基-苯丙氨酸衍生物对胰岛素肠道吸收具有辅效应的化学结构性质如下：1. 芳环存在，与酰基羰基相隔两个原子。2. 图2中的X或Y之一为氧，或者X-Y是双键。3. N-酰基部分具有较小的疏水取代基，如F、Cl或Me在Rα、Rβ、Rη位置，并且整个分子具有适当的亲水-疏水平衡。利用这些制剂增强胰岛素吸收，为口服胰岛素治疗提供了新的途径。
• Highly Selective Reaction of α-Halo-α,β-unsaturated Esters with Ketones or Aldehydes Promoted by SmI₂:  An Efficient Alternative Access to Baylis−Hillman Adducts
  作者：José M. Concellón、Mónica Huerta

  DOI：10.1021/jo0504969

  日期：2005.6.1

  A samarium diiodide promoted addition of aromatic or aliphatic β-substituted-α-halo-α,β-unsaturated esters 1 or 3 to both ketones (in THF) and aldehydes (in acetonitrile) led to (Z)-2-(1-hydroxyalkyl)-2,3-alkenoates 2 and 4 in good yields and very high stereoselectivity. This method constitutes an efficient and valuable alternative to the synthesis of Baylis−Hillman adducts. A mechanism is proposed

  二碘化sa促进芳香族或脂肪族β-取代-α-卤代-α，β-不饱和酯1或3加到酮（在THF中）和醛（在乙腈中）上，导致（Z）-2-（1-羟基烷基）-2,3-链烯酸酯2和4的收率和立体选择性很高。该方法构成了Baylis-Hillman加合物合成的有效且有价值的替代方法。提出了一种机制来解释这种转变。
• Ir(ppy)₃-Catalyzed, Visible-Light-Mediated Reaction of α-Chloro Cinnamates with Enol Acetates: An Apparent Halogen Paradox
  作者：Thomas Föll、Julia Rehbein、Oliver Reiser

  DOI：10.1021/acs.orglett.8b02484

  日期：2018.9.21

  activation of vinyl chlorides derived from α-chloro ethyl cinnamates via oxidative quenching of excited photocatalyst fac-Ir(ppy)3 is described. Upon photoelectron transfer and chloride extrusion, the corresponding vinyl radical can be efficiently trapped by enol acetates, giving rise to synthetically useful 1,4-dicarbonyl compounds in good to excellent yields. This transformation is distinguished by

  描述了由α-氯乙基肉桂酸酯衍生的氯乙烯的可见光介导的活化，该活化是通过激发光催化剂fac -Ir（ppy）3的氧化猝灭。在光电子转移和氯化物挤出时，相应的乙烯基可以被烯醇乙酸酯有效地捕集，从而以良好的至优异的产率产生了合成上有用的1，4-二羰基化合物。这种转化的特征是温和且对环境无害的反应条件，并且可以在数克范围内进行，这与对比的α-溴乙基肉桂酸酯形成鲜明对比，后者在各种条件下均显示出低转化率。
• Catalyst and method for converting low molecular weight paraffinic hydrocarbons into alkenes
  申请人：Bagherzadeh Ebrahim

  公开号：US20060135838A1

  公开（公告）日：2006-06-22

  A process and catalyst for the partial oxidation of low molecular weight paraffinic hydrocarbons, such as methane, ethane, propane, naphtha, and natural gas condensates to form alkenes, such as ethylene, propylene and other valuable by-products. The process involves contacting the low molecular weight paraffinic hydrocarbon with the catalyst in the presence of oxygen or air and optionally steam. The catalyst has a perovskite-type crystalline structure, and lends itself to fixed and fluidized bed reactor configurations. The conversion process is less costly than conventional processes due to low pressure operation, the use of air and steam as a source of oxygen, and lower operating temperatures resulting in less coking, downtime, and reduced cost for materials of construction. Catalyst activity is extended and reactor downtime for catalyst regeneration is minimized by addition of chlorides and/or amines.

  一种用于部分氧化低分子量烷烃烃类碳氢化合物（如甲烷、乙烷、丙烷、石脑油和天然气凝析液）以形成烯烃（如乙烯、丙烯等）和其他有价值的副产品的过程和催化剂。该过程涉及将低分子量烷烃烃类碳氢化合物与催化剂在氧气或空气以及可选的蒸汽存在下接触。催化剂具有钙钛矿型的晶体结构，并适用于固定床和流化床反应器结构。由于低压操作、使用空气和蒸汽作为氧源以及较低的操作温度导致较少的结焦、停机时间和降低建筑材料成本，转化过程比传统工艺成本更低。通过添加氯化物和/或胺，延长了催化剂的活性并将用于催化剂再生的反应器停机时间最小化。
• Ru-catalyzed highly chemo- and enantioselective hydrogenation of γ-halo-γ,δ-unsaturated-β-keto esters under neutral conditions
  作者：Xin Ma、Wanfang Li、Xiaoming Li、Xiaoming Tao、Weizheng Fan、Xiaomin Xie、Tahar Ayad、Virginie Ratovelomanana-Vidal、Zhaoguo Zhang

  DOI：10.1039/c2cc30925d

  日期：——

  Finely-tuned ruthenium-catalyzed highly chemoselective and enantioselective hydrogenation of gamma-halo-gamma,delta-unsaturated-beta-keto esters at the carbonyl group was achieved under neutral reaction conditions (ee up to 97%). Both olefin and alkenyl halogen moieties, which are labile under hydrogenation conditions, remained untouched during the reaction.

  在中性反应条件下（ee高达97％），实现了钌的精细调节，催化了羰基上的gamma-卤代-gamma，δ-不饱和β-酮酸酯的高度化学选择性和对映选择性氢化。在氢化条件下不稳定的烯烃和烯基卤素部分都在反应过程中保持不变。

表征谱图