3-methoxy-cinnamic acid methyl ester | 15854-56-5

• 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
• 英文名称: 3-methoxy-cinnamic acid methyl ester
• 英文别名: meta-methoxycinnamic acid methyl ester；methyl m-methoxycinnamate；methyl 3-methoxycinnamate；methyl (3-methoxyphenyl)prop-2-enoate；m-Methoxyzimtsaeuremethylester；Methylaether-m-cumarsaeure-methylester；O-Methyl-m-cumarsaeure-methylester；3-Methoxy-zimtsaeure-methylester；methyl 3-(3-methoxyphenyl)prop-2-enoate
• CAS: 15854-56-5
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: NDMAAKFMVKZYIV-UHFFFAOYSA-N

物化性质

• 熔点：
  57 °C
• 沸点：
  300.0±15.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-cinnamic acid methyl ester 在 二苯基甲烷 、 二苯基膦叠氮化物 、 三乙胺 、 sodium hydroxide 作用下， 以 甲苯 为溶剂， 生成 6-甲氧基异喹啉-1(2H)-酮
  参考文献：
  名称：

  Optimisation of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors

  摘要：

  Rho kinase is an important target implicated in a variety of cardiovascular diseases. Herein, we report the optimisation of the fragment derived ATP-competitive ROCK inhibitors 1 and 2 into lead compound 14A. The initial goal of improving ROCK-I potency relative to 1, whilst maintaining a good PK profile, was achieved through removal of the aminoisoquinoline basic centre. Lead 14A was equipotent against both ROCK-I and ROCK-II, showed good in vivo efficacy in the spontaneous hypertensive rat model, and was further optimised to demonstrate the scope for improving selectivity over PKA versus hydroxy Fasudil 3. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.104
• 作为产物：
  描述：

  3-甲氧基肉桂酸 生成 3-methoxy-cinnamic acid methyl ester
  参考文献：
  名称：

  Rieche, Chemische Berichte, 1889, vol. 22, p. 2354

  摘要：

  DOI：

文献信息

• Enantioselective Synthesis of Pyroglutamic Acid Esters from Glycinate via Carbonyl Catalysis
  作者：Jiguo Ma、Qinghai Zhou、Guanshui Song、Yongchang Song、Guoqing Zhao、Kuiling Ding、Baoguo Zhao

  DOI：10.1002/anie.202017306

  日期：2021.5.3

  Direct α‐functionalization of NH2‐free glycinates with relatively weak electrophiles such as α,β‐unsaturated esters still remains a big challenge in organic synthesis. With chiral pyridoxal 5 d as a carbonyl catalyst, direct asymmetric conjugated addition at the α‐C of glycinate 1 a with α,β‐unsaturated esters 2 has been successfully realized, to produce various chiral pyroglutamic acid esters 4 in 14–96 %

  用相对较弱的亲电试剂（例如，α，β-不饱和酯）将不含NH 2的甘氨酸直接进行α-官能化仍然是有机合成中的一大挑战。以手性吡ido醛5 d作为羰基催化剂，已成功实现在甘氨酸1a的α-C与α，β-不饱和酯2的直接不对称共轭加成反应，以14-96％的收率生产各种手性焦谷氨酸酯4原位内酰胺化后具有81–97％ee的物质。该反式与顺非对映异构体可以通过色谱法同时获得，并且可以很容易地通过叔丁基去除和随后的Barton转化为手性4取代的吡咯烷-2-酮，例如具有相同绝对构型的阿兹海默氏药物Rolipram（11）。脱羧。
• Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst
  作者：Jingjing Wang、Feng Jiang、Chaofu Tao、Han Yu、Laurent Ruhlmann、Yongge Wei

  DOI：10.1039/d1gc00161b

  日期：——

  direct esterification of alcohols with non-noble metal-based catalytic systems faces great challenges. Here, we report a new chrome-based catalyst stabilized by a single pentaerythritol decorated Anderson-type polyoxometalate, [N(C4H9)4]3[CrMo6O18(OH)3C(OCH2)3CH2OH}], which can realize the efficient transformation from alcohols to esters by H2O2 oxidation in good yields and high selectivity without

  醇与基于非贵金属的催化体系直接酯化面临巨大挑战。在这里，我们报告了一种由单季戊四醇修饰的安德森型多金属氧酸盐[N（C 4 H 9）4 ] 3 [CrMo 6 O 18（OH）3 C （OCH 2）3 CH 2 OH}]，可以实现H 2 O 2从醇到酯的高效转化无需额外的有机配体，即可以高收率和高选择性进行氧化。该系统可耐受各种功能不同的醇，包括某些天然产物和医药中间体。铬基催化剂可以循环使用几次，并且仍保持原始配置和催化活性。我们还提出了合理的催化机制，并证明了其在工业上的应用潜力。
• Palladium(II)-Schiff base complex immobilized covalently on h-BN: An efficient and recyclable catalyst for aqueous organic transformations
  作者：Weijian Li、Guanghui Lv、Xu Cheng、Rui Sang、Xiaojun Ma、Yong Zhang、Ruifang Nie、Jie Li、Mei Guan、Yong Wu

  DOI：10.1016/j.tet.2016.11.027

  日期：2016.12

  air-stable palladium(II)-Schiff base complex supported on h-BN was simply prepared by using commercially available reagents. This nanomaterial was applied as an excellent and recyclable heterogeneous catalyst for the Suzuki and Heck cross-coupling reactions. And it has been characterized by FT-IR, XRD, SEM, XPS, TG and ICP-AES techniques. High yields, ligand-free, low reaction time, water as solvent

  负载在h-BN上的水分和空气稳定的钯（II）-席夫碱复合物只需使用市售试剂即可制备。这种纳米材料被用作Suzuki和Heck交叉偶联反应的优良且可回收的非均相催化剂。并且已通过FT-IR，XRD，SEM，XPS，TG和ICP-AES技术进行了表征。这些方案的主要优点是高收率，无配体，反应时间短，以水为溶剂，无毒和可回收的催化剂。另外，使用该催化剂成功地合成了一系列药理上相关的产物。最重要的是，这项工作为使用h-BN作为多相催化剂的有效载体开辟了一条有趣的诱人途径。
• Cross-Linked Thiazolidine Network as Support for Palladium: A New Catalyst for Suzuki and Heck Reactions
  作者：Lucia Anna Bivona、Francesco Giacalone、Luigi Vaccaro、Carmela Aprile、Michelangelo Gruttadauria

  DOI：10.1002/cctc.201500408

  日期：2015.8.17

  sodium borohydride afforded a thiazolidine‐based material that acted as ligands for the Pd species. The thiazolidine‐based palladium catalyst was fully characterized and, working in only 0.1 mol % amount, displayed good activity in the Suzuki–Miyaura and in the Heck reactions. Several biphenyl and alkene compounds could be prepared in high yields. The catalytic material proved to be fully recoverable and

  噻唑烷基材料首次用作钯的载体。支撑物是从高度交联的噻唑基材料开始制备的，该材料是在3-巯基丙基改性的二氧化硅SBA-15的存在下，将二乙烯基双乙烯基噻唑鎓二溴化物盐自由基低聚得到的。通过用四氯钯盐处理来固定钯。用硼氢化钠还原可得到基于噻唑烷的材料，该材料可作为Pd的配体。噻唑烷基钯催化剂已得到充分表征，仅以0.1 mol％的量工作，在Suzuki-Miyaura和Heck反应中显示出良好的活性。可以高收率制备几种联苯和烯烃化合物。
• Novel cyclodextrin-modified h-BN@Pd(II) nanomaterial: An efficient and recoverable catalyst for ligand-free C-C cross-coupling reactions in water
  作者：Xiaojun Ma、Guanghui Lv、Xu Cheng、Weijian Li、Rui Sang、Yong Zhang、Qiantao Wang、Li Hai、Yong Wu

  DOI：10.1002/aoc.3854

  日期：2017.12

  An environmentally friendly palladium(II) catalyst supported on cyclodextrin‐modified h‐BN was successfully prepared. The catalyst was characterized by FT‐IR, SEM, TG, XRD and XPS, and the loading level of Pd in h‐BN@β‐CD@Pd(II) was measured to be 0.088 mmol g−1 by ICP. It exhibits excellent catalytic activity for the Suzuki and Heck reactions in water, and can be easily separated and consecutively

  已成功制备了负载在环糊精修饰的h-BN上的环保钯（II）催化剂。通过FT-IR，SEM，TG，XRD和XPS对催化剂进行了表征，ICP测得h-BN @β-CD@ Pd（II）中Pd的负载量为0.088 mmol g -1。它对水中的Suzuki和Heck反应具有出色的催化活性，并且可以轻松分离并连续重复使用至少9次。此外，使用该催化剂成功合成了一系列药理学有趣的产品，以证明其在制药工业中的潜在应用。最重要的是，这项工作为使用环糊精官能化的h-BN作为亲水性非均相催化剂的有效载体开辟了一条有趣的诱人途径。