(4-甲基-2-乙烯基苯基)氨基甲酸叔丁酯 | 809231-04-7

• 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: (4-甲基-2-乙烯基苯基)氨基甲酸叔丁酯
• 英文名称: (4-methyl-2-vinylphenyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-(2-ethenyl-4-methylphenyl)carbamate
• CAS: 809231-04-7
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: DICKFDFDHFSUQU-UHFFFAOYSA-N

物化性质

• 熔点：
  87-89 °C
• 沸点：
  292.2±29.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-甲基-2-乙烯基苯基)氨基甲酸叔丁酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到4-methyl-2-vinylaniline
  参考文献：
  名称：

  铑催化的串联共轭加成反应-曼尼希环化反应：直接获得完全取代的四氢喹啉

  摘要：

  已开发出一种新的Rh（I）催化的串联共轭加成反应-亚胺取代的电子缺陷烯烃与芳基硼酸的曼尼希环化反应，得到2,3,4-三取代的1,2,3,4-四氢喹啉。这是第一个涉及亚胺基作为Rh（I）催化串联反应中的第二亲电子试剂的例子。

  DOI：

  10.1021/jo800914c
• 作为产物：
  描述：

  2-溴-4-甲基苯胺 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 62.0h， 生成 (4-甲基-2-乙烯基苯基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Indole Synthesis by Controlled Carbolithiation of o-Aminostyrenes

  摘要：

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.

  DOI：

  10.1021/jo048723e

文献信息

• Carbamato-benzylidene ruthenium chelates – Synthesis, structure and catalytic activity in olefin metathesis
  作者：Szymon Rogalski、Patrycja Żak、Piotr Pawluć、Maciej Kubicki、Cezary Pietraszuk

  DOI：10.1016/j.jorganchem.2018.01.032

  日期：2018.3

  4-diacetoxybut-2-ene, the complexes behave like latent catalysts. Complexes remain completely inactive until they are activated by the addition of ethereal solution of HCl. The presence of the electron-withdrawing group results in a slight increase in the catalytic activity of the activated form of the catalyst relative to a similar form of the unsubstituted complex or the least active complex carrying the electron

  通过第一代[RuCl 2（PCy 3）2（= CHPh）]和第二代[RuCl 2（SIMes）（PCy 3）（= CHPh）]通过交换置换合成了新的氨基甲酸酯-κN-亚苄基钌螯合物。位置上对位带有亚苄基配体的叔丁基（2-乙烯基苯基）氨基甲酸酯的亚苄基配体的合成具有甲基或三氟甲基的氨基甲酸酯官能团。在测试的所有复分解转化中，即在环辛-1,5-二烯的ROMP中，二烯丙基丙二酸二乙酯和2-烯丙基-2-（2-甲基烯丙基）丙二酸二乙酯的RCM以及烯丙基苯与Z-1,4-二乙酰氧基丁酸酯的交叉复分解-2-烯，络合物的行为类似于潜在催化剂。络合物保持完全无活性，直到通过加入HCl的醚溶液将其活化为止。相对于带有供电子基团的未取代配合物或活性最低的配合物的类似形式，吸电子基团的存在导致催化剂活化形式的催化活性略有增加。
• Indole Synthesis by Controlled Carbolithiation of <i>o</i>-Aminostyrenes
  作者：Albane Kessler、Claire M. Coleman、Patchanee Charoenying、Donal F. O'Shea

  DOI：10.1021/jo048723e

  日期：2004.11.1

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.
• Rhodium-Catalyzed Tandem Conjugate Addition−Mannich Cyclization Reaction: Straightforward Access to Fully Substituted Tetrahydroquinolines
  作者：So Won Youn、Ju-Hyun Song、Dai-Il Jung

  DOI：10.1021/jo800914c

  日期：2008.7.1

  A new Rh(I)-catalyzed tandem conjugate addition−Mannich cyclization reaction of imine-substituted electron-deficient alkenes with arylboronic acids has been developed to afford 2,3,4-trisubstituted 1,2,3,4-tetrahydroquinolines. This is the first example involving imine group as a secondary electrophile in Rh(I)-catalyzed tandem reactions.

  已开发出一种新的Rh（I）催化的串联共轭加成反应-亚胺取代的电子缺陷烯烃与芳基硼酸的曼尼希环化反应，得到2,3,4-三取代的1,2,3,4-四氢喹啉。这是第一个涉及亚胺基作为Rh（I）催化串联反应中的第二亲电子试剂的例子。