methyl (E)-2-methyl-3-(4-(trifluoromethyl)phenyl)acrylate | 220654-86-4

• 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
• 英文名称: methyl (E)-2-methyl-3-(4-(trifluoromethyl)phenyl)acrylate
• 英文别名: (E)-methyl 2-methyl-3-(4-(trifluoromethyl)phenyl)acrylate；(E)-[2-methyl-3-(4-trifluoromethylphenyl)]-2-propenoic acid methyl ester；alpha-Methyl-4-(trifluoromethyl)-trans-cinnamic acid methyl ester；methyl (E)-2-methyl-3-[4-(trifluoromethyl)phenyl]prop-2-enoate
• CAS: 220654-86-4
• 化学式: C₁₂H₁₁F₃O₂
• 分子量: 244.213
• InChiKey: ZXHUDHWLCZINTB-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-methyl-3-(4-(trifluoromethyl)phenyl)acrylate 在 N-氯代丁二酰亚胺 、 三氯化铝 、 lithium aluminium deuteride 、 二甲基硫 作用下， 生成 1-trifluoromethyl-4-[(E)-2-methyl-3,3,3-trideuterio-1-propenyl]benzene
  参考文献：
  名称：

  通过氘标记的三取代烯烃的亚硝基芳烃烯反应中的空间和电子效应，通过单独的取代基控制区域选择性。

  摘要：

  对于4-硝基亚硝基苯（ArNO）与多种伯和仲孤烷基取代的底物的烯反应，twix / twin区域选择性恒定在约85:15。相反，对于单独的叔丁基和对于单独的芳基取代基，仅获得twix区域异构体。这些区域选择性已经在第一步反应的过渡态中，在亲和体与底物之间的空间相互作用和配位方面得到了合理化。

  DOI：

  10.1021/jo026198i
• 作为产物：
  描述：

  methyl 2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)acrylate 在 (S)-DTBM-MeOBIPHEP 、 copper(II) acetate monohydrate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以97%的产率得到methyl (E)-2-methyl-3-(4-(trifluoromethyl)phenyl)acrylate
  参考文献：
  名称：

  Morita–Baylis–Hillman加合物的氢化铜还原反应中化学，区域和对映选择性的控制

  摘要：

  非消旋连接的氢化铜可用于串联S N 2'/ 1,2-还原外消旋的森田-贝利斯-希尔曼（MBH）乙酸酯，以得到具有定义的烯烃几何形状的对映体富集的手性烯丙基醇。MBH酯（包括具有β取代基的酯）可以利用庞大的，低聚的，原位生成的三烷氧基硅氧烷离去基团转化为立体定义的烯酸酯。最后，公开了容易到达的MBH醇衍生物向非外消旋烯丙基醇的非典型转化。

  DOI：

  10.1021/acs.orglett.6b03464

文献信息

• Copper-catalyzed diastereoselective synthesis of β-boryl-α-quaternary carbon carboxylic esters
  作者：Ya-Jie Zuo、Zhuoran Zhong、Yinkun Fan、Xiangyu Li、Xiaolu Chen、Yuwei Chang、Ruihu Song、Xinpeng Fu、Anling Zhang、Chong-Min Zhong

  DOI：10.1039/c8ob02469c

  日期：——

  skeletons of dialkyl sulfates, primary allyl halides, and benzyl bromides were transferred to the α-position of the substrates to provide products in moderate to good yields with a diastereoselectivity of >95% in most cases. Substrates bearing a β-(hetero)aryl substituent gave higher diastereoselectivities than those bearing a linear β-alkyl substituent. The crystal structure of the potassium trifluoroborate

  开发了Cu（I）催化α-烷基取代的α，β-不饱和羧酸酯的非对映选择性碳硼化反应，生成β-硼基-α-季碳酸酯。将硫酸二烷基酯，伯烯丙基卤和苄基溴的碳骨架转移到底物的α位，以中等至良好的收率提供产物，在大多数情况下，非对映异构体选择性> 95％。带有β-（杂）芳基取代基的底物比带有线性β-烷基取代基的底物具有更高的非对映选择性。三氟硼酸钾衍生物的晶体结构表明该反应可能通过铜（I）烯醇中间产物，非对映选择性是由亲电子体对烯醇较少受阻侧的亲电子攻击引起的。
• Anthranilic acid analogs
  申请人：American Home Products Corporation

  公开号：US06046239A1

  公开（公告）日：2000-04-04

  Compounds of the formula: ##STR1## wherein: R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 are, independently, hydrogen, COOR.sub.15, halogen, nitro, cyano, C.sub.1-10 alkoxy, C.sub.1-10 haloalkoxy, sulfonic acid, C.sub.1-10 alkylsulfonyl, C.sub.6-12 arylsulfonyl, C.sub.6-12 aralkylsulfonyl, C.sub.1-10 alkylsulfinyl, C.sub.6-12 alkylsulfinyl, C.sub.6-12 aralkylsulfinyl, sulfamoyl, C.sub.1-10 alkylsulfamido, C.sub.6-12 alkylsulfamido, C.sub.1-10 alkanoyl, C.sub.6-12 aryloyl, C.sub.6-12 aralkanoyl, amino, C.sub.1-10 alkylamino, C.sub.2-10 dialkylamino, C.sub.6-12 aralkylamino, C.sub.6-12 arylamino, carboxamido, C.sub.1-10 alkylcarboxamido, C.sub.6-12 arylcarboxamido, C.sub.1-10 haloalkyl, C.sub.1-10 alkyl, C.sub.2-12 alkenyl, C.sub.6-12 aryl, C.sub.6-12 aralkyl; with the proviso that at least one of R.sub.4 and R.sub.5 is COOR.sub.15 ; R.sub.9 is hydrogen, C.sub.1-10 alkyl and C.sub.1-10 haloalkyl; R.sub.10 is hydrogen, C.sub.1-10 alkyl, C.sub.1-10 haloalkyl, or C.sub.2-12 alkylidene; R.sub.15 is hydrogen, metal cation, acetylamido, alkoxyacetoyl or a related moiety which delivers the carboxylate in vivo; the dotted line is an optional double bond; with the proviso that when R.sub.10 is an alkylidene moiety, the double bond is absent; and W is nitrogen or carbon bearing a hydrogen, or R.sub.4, R.sub.5 or R.sub.6 as hereinbefore defined; or pharmaceutical salts thereof, are useful in the treatment of disorders associated with smooth muscle contraction via potassium channel and chloride channel modulation.

  式为##STR1##的化合物，其中：R.sub.1、R.sub.2、R.sub.3、R.sub.4、R.sub.5、R.sub.6、R.sub.7和R.sub.8分别独立地为氢、COOR.sub.15、卤素、硝基、氰基、C.sub.1-10烷氧基、C.sub.1-10卤代烷氧基、磺酸、C.sub.1-10烷基磺酰基、C.sub.6-12芳基磺酰基、C.sub.6-12芳基烷基磺酰基、C.sub.1-10烷基亚磺酰基、C.sub.6-12烷基亚磺酰基、C.sub.6-12芳基烷基亚磺酰基、磺酰胺基、C.sub.1-10烷基磺酰胺基、C.sub.6-12烷基磺酰胺基、C.sub.1-10酰基、C.sub.6-12芳基酰基、C.sub.6-12芳基烷基酰基、氨基、C.sub.1-10烷基氨基、C.sub.2-10二烷基氨基、C.sub.6-12芳基烷基氨基、C.sub.6-12芳基氨基、羧酰胺基、C.sub.1-10烷基羧酰胺基、C.sub.6-12芳基羧酰胺基、C.sub.1-10卤代烷基、C.sub.1-10烷基、C.sub.2-12烯基、C.sub.6-12芳基、C.sub.6-12芳基烷基；但至少有R.sub.4和R.sub.5中的一个为COOR.sub.15；R.sub.9为氢、C.sub.1-10烷基和C.sub.1-10卤代烷基；R.sub.10为氢、C.sub.1-10烷基、C.sub.1-10卤代烷基或C.sub.2-12烷基亚基；R.sub.15为氢、金属阳离子、乙酰胺基、烷氧乙酰基或在体内释放羧酸根的相关基团；虚线为可选的双键；但当R.sub.10为烷基亚基时，双键不存在；且W为氮或碳，带有氢、或如上所定义的R.sub.4、R.sub.5或R.sub.6；或其制药盐，在通过钾通道和氯通道调节治疗平滑肌收缩相关疾病方面有用。
• Stereoelectronic and solvent effects on the allylic oxyfunctionalization of alkenes with singlet oxygen
  作者：Mariza N. Alberti、Michael Orfanopoulos

  DOI：10.1016/j.tet.2006.07.106

  日期：2006.11

  control the stereochemistry of sensitized photooxygenation of alkenes via singlet oxygen (ene reaction) are selectively reported. We also introduce our most recent stereoelectronic effects on the singlet oxygen–ene reaction. The origin of site selectivity and solvent-dependent stereoselectivity in this classical ene reaction with simple as well as functionalized alkenes is highlighted. These studies

  有选择地报道了控制经由单线态氧（烯烃反应）的烯烃的敏化光氧化的立体化学的因素。我们还介绍了我们对单线态氧-烯反应的最新立体电子效应。在这种经典的烯键反应中，无论是简单的还是官能化的烯烃，其位点选择性和溶剂依赖性立体选择性的起源都得到了强调。这些研究和其他类似研究大大提高了单线态氧在天然和非天然产物合成中的效用。
• Pd-Catalyzed Sequential C–C Bond Formation and Cleavage: Evidence for an Unexpected Generation of Arylpalladium(II) Species
  作者：So Won Youn、Byung Seok Kim、Arun R. Jagdale

  DOI：10.1021/ja304616q

  日期：2012.7.18

  A Pd(II)-catalyzed reaction engaging alkenyl beta-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium-(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven beta-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.
• ANTHRANILIC ACID ANALOGS
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP1003712A1

  公开（公告）日：2000-05-31