(1R,2R)-1,2-diphenylbut-3-en-1-amine | 1380611-73-3

• 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: (1R,2R)-1,2-diphenylbut-3-en-1-amine
• CAS: 1380611-73-3
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: VDJNGOLBZQHMER-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1,2-diphenylbut-3-en-1-amine 在 Schwartz's reagent 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2R,3R)-2,3-diphenylpyrrolidine
  参考文献：
  名称：

  Switching Regioselectivity in the Allylation of Imines by N-Side Chain Tuning

  摘要：

  A spectacular inversion of alpha- to gamma-regioselectivity in the allylzincation of imines can be achieved by fine-tuning of the N-side chain. This approach allows easy preparation of regioisomeric amines, in racemic as well as enantiopure forms. The usefulness of the method is illustrated by the parallel asymmetric syntheses of 2,3- and 2,5-diphenylpyrrolidines.

  DOI：

  10.1021/ol301026w
• 作为产物：
  描述：

  苯乙醇,b-[(苯基亚甲基)氨基]-,(R)- 在 lead(IV) tetraacetate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 (1R,2R)-1,2-diphenylbut-3-en-1-amine
  参考文献：
  名称：

  Switching Regioselectivity in the Allylation of Imines by N-Side Chain Tuning

  摘要：

  A spectacular inversion of alpha- to gamma-regioselectivity in the allylzincation of imines can be achieved by fine-tuning of the N-side chain. This approach allows easy preparation of regioisomeric amines, in racemic as well as enantiopure forms. The usefulness of the method is illustrated by the parallel asymmetric syntheses of 2,3- and 2,5-diphenylpyrrolidines.

  DOI：

  10.1021/ol301026w

文献信息

• Dramatic lithium chloride effect on the reaction stereocontrol in Zn-mediated asymmetric cinnamylation: highly practical synthesis of β-aryl homoallylic amines
  作者：Min Liu、An Shen、Xing-Wen Sun、Fei Deng、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1039/c0cc03230a

  日期：——

  An extremely mild and practical approach for the preparation of enantiomerically enriched beta-aryl substituted homoallylic amines bearing two adjacent stereogenic centers was realized by room temperature zinc-mediated highly stereoselective cinnamylation of N-sulfinyl imines.

  通过室温锌介导的N-亚磺酰基亚胺的高度立体选择性肉桂基化，实现了一种极其温和且实用的方法，用于制备带有两个相邻立体异构中心的对映异构体富集的β-芳基取代的均烯丙基胺。
• Switching Regioselectivity in the Allylation of Imines by N-Side Chain Tuning
  作者：Pierre-Olivier Delaye、Jean-Luc Vasse、Jan Szymoniak

  DOI：10.1021/ol301026w

  日期：2012.6.15

  A spectacular inversion of alpha- to gamma-regioselectivity in the allylzincation of imines can be achieved by fine-tuning of the N-side chain. This approach allows easy preparation of regioisomeric amines, in racemic as well as enantiopure forms. The usefulness of the method is illustrated by the parallel asymmetric syntheses of 2,3- and 2,5-diphenylpyrrolidines.