(E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)-N-methylethanamine | 74904-71-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)-N-methylethanamine
• 英文别名: 2-[2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-4,5-dimethoxyphenyl]-N-methylethanamine
• CAS: 74904-71-5
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: SYWGAEOWGCHAPF-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)-N-methylethanamine 在 正丁基锂 、 (4S,4'S)-2,2'-(propane-2,2-diyl)bis(4-iso-butyl-4,5-dihydrooxazole) 、 二异丙胺 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 26.0h， 以64%的产率得到(S)-劳丹素
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of (S)-Laudanosine by Hydroamination

  摘要：

  Lithium amide-chiral bisoxazoline-catalyzed asymmetric intramolecular hydroamination was examined with respect to the structural variants of starting aminoalkenes. Substituents on the nitrogen and olefin of aminoalkenes were found to be important factors affecting reaction efficiency as well as enentioselectivity in the production of chiral tetrahydroisoquinolines and isoindolines. The catalytic asymmetric total synthesis of (S)-laudanosine highlights the utility of the asymmetric hydroamination.

  DOI：

  10.3987/com-12-s(n)44
• 作为产物：
  描述：

  (E)-N-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)formamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以92%的产率得到(E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)-N-methylethanamine
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of (S)-Laudanosine by Hydroamination

  摘要：

  Lithium amide-chiral bisoxazoline-catalyzed asymmetric intramolecular hydroamination was examined with respect to the structural variants of starting aminoalkenes. Substituents on the nitrogen and olefin of aminoalkenes were found to be important factors affecting reaction efficiency as well as enentioselectivity in the production of chiral tetrahydroisoquinolines and isoindolines. The catalytic asymmetric total synthesis of (S)-laudanosine highlights the utility of the asymmetric hydroamination.

  DOI：

  10.3987/com-12-s(n)44

文献信息

• Cleavage of 1-Benzyltetrahydroisoquinolines to Secondary Amines via Urethanes
  作者：Wan-Joo Kim、Dong-Ung Lee、Wolfgang Wiegrebe

  DOI：10.1002/ardp.19843170512

  日期：——

  2,2,2‐Trichloroethyl chloroformate and benzyl chloroformate cleave 1‐benzyl‐1,2,3,4‐tetrahydro‐2‐methylisoquinolines of type 1 to yield tertiary stilbene urethanes of type 2 which are easily reduced or hydrogenolyzed to secondary amines. 6′‐(Hydroxymethyl)‐laudanosine (4) is converted by these reagents to the isochroman urethanes 11 and 12 which are split to yield the secondary amine 8 without the

  2,2,2-氯甲酸三氯乙酯和氯甲酸苄酯裂解1-苄基-1,2,3,4-四氢-2-甲基异喹啉，生成2型叔二苯乙烯氨基甲酸酯，它很容易还原或氢解为仲胺。6 ' -（羟甲基）-月桂醇苷 (4) 被这些试剂转化为异色满氨基甲酸乙酯 11 和 12，它们被分裂成仲胺 8，而异色满部分没有受到攻击。
• Asymmetric total synthesis of (−)-javaberine A and (−)-epi-javaberine A based on catalytic intramolecular hydroamination of N-methyl-2-(2-styrylaryl)ethylamine
  作者：Saho Uenishi、Rina Kakigi、Kumiko Hideshima、Akari Miyawaki、Junpei Matsuoka、Tokutaro Ogata、Kiyoshi Tomioka、Yasutomo Yamamoto

  DOI：10.1016/j.tet.2021.132165

  日期：2021.6

  Asymmetric total synthesis of (–)-javaberine A and its epimer was achieved by utilizing two methods for isoquinoline synthesis, asymmetric hydroamination of N-methyl-2-(2-styrylaryl)ethylamine and Bischler-Napieralski cyclization. Intramolecular asymmetric hydroamination of N-methyl aminoalkene 4 was catalyzed by lithium amide–chiral bisoxazoline to give tetrahydroisoquinoline (S)-laudanosine with

  （-）-javaberine A及其差向异构体的不对称总合成是利用两种异喹啉合成方法：N-甲基-2-（2-苯乙烯基芳基）乙胺的不对称加氢胺化和Bischler-Napieralski环化而实现的。酰胺锂-手性双恶唑啉催化N-甲基氨基烯烃4的分子内不对称氢化胺化反应，得到对映体选择性好，产率高的四氢异喹啉（S）-月桂肌苷。（S）-月桂肌苷的N-脱甲基通过Polonovski-型反应完成，得到（S）-去甲月桂肌苷。（S的凝结）-去甲月桂花碱和高鸟氨酸，随后进行Bischler-Napieralski环化，LiAlH 4还原和O-去甲基化，提供了（8 R，14 S）-（-）-javaberine A，对应于天然javaberine A的对映体。（8 S，还成功地合成了14 S）-（–）-Javaberine A，它对应于天然Javaberine A的C14-顶基。
• c. The characterization and thermolysis of cis- and trans-(¦)-laudanosine N-oxide
  作者：JB Bremner、LV Thuc

  DOI：10.1071/ch9800379c

  日期：——
• KIM, WAN-JOO;LEE, DONG-UNG;WIEGREBE, W., ARCH. PHARM., 1984, 317, N 5, 438-442
  作者：KIM, WAN-JOO、LEE, DONG-UNG、WIEGREBE, W.

  DOI：——

  日期：——
• Catalytic Asymmetric Synthesis of (S)-Laudanosine by Hydroamination
  作者：Kiyoshi Tomioka、Tokutaro Ogata、Tetsutaro Kimachi、Ken-ichi Yamada、Yasutomo Yamamoto

  DOI：10.3987/com-12-s(n)44

  日期：——

  Lithium amide-chiral bisoxazoline-catalyzed asymmetric intramolecular hydroamination was examined with respect to the structural variants of starting aminoalkenes. Substituents on the nitrogen and olefin of aminoalkenes were found to be important factors affecting reaction efficiency as well as enentioselectivity in the production of chiral tetrahydroisoquinolines and isoindolines. The catalytic asymmetric total synthesis of (S)-laudanosine highlights the utility of the asymmetric hydroamination.