(R)-1-phenylbuta-2,3-dienylamine | 566950-11-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1-phenylbuta-2,3-dienylamine
• 英文别名: (+)-(R)-1-phenylbuta-2,3-dien-1-ylamine
• CAS: 566950-11-6
• 化学式: C₁₀H₁₁N
• 分子量: 145.204
• InChiKey: TWSCZIJOLDJJQC-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (R)-1-phenylbuta-2,3-dienylamine 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以73%的产率得到(R)-1-苯基丁胺
  参考文献：
  名称：

  Asymmetric Synthesis of Allyl- and α-Allenylamines from Chiral Imines and Alkynes via (η²-Imine)Ti(O-i-Pr)₂ Complexes

  摘要：

  [GRAPHICS]The reaction of a divalent titanium reagent Ti(O-1-Pr)(4)/2i-PrMgX with optically active arylaidimines derived from arylaidehydes and O-methylphenylglycinol provided, in a highly diastereoselective manner, chiral (eta(2)-imine)Ti(O-i-Pr)(2) complexes, which in turn reacted with 1-alkynes or propargyl compounds to give optically active allyl- and alpha-allenylamines, respectively.

  DOI：

  10.1021/ol034599u
• 作为产物：
  描述：

  (R)-benzylidene-(2-methoxy-1-phenylethyl)amine 在 titanium(IV) isopropylate 、 异丙基氯化镁 、 三溴化硼 、 高碘酸 、 甲胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 19.0h， 生成 (R)-1-phenylbuta-2,3-dienylamine
  参考文献：
  名称：

  Asymmetric Synthesis of Allyl- and α-Allenylamines from Chiral Imines and Alkynes via (η²-Imine)Ti(O-i-Pr)₂ Complexes

  摘要：

  [GRAPHICS]The reaction of a divalent titanium reagent Ti(O-1-Pr)(4)/2i-PrMgX with optically active arylaidimines derived from arylaidehydes and O-methylphenylglycinol provided, in a highly diastereoselective manner, chiral (eta(2)-imine)Ti(O-i-Pr)(2) complexes, which in turn reacted with 1-alkynes or propargyl compounds to give optically active allyl- and alpha-allenylamines, respectively.

  DOI：

  10.1021/ol034599u

文献信息

• Asymmetric Propargylboration of Aldimines and Ketimines with the Borabicyclo[3.3.2]decanes: Novel Entries to Allenyl Carbinamines, Amino Acids, and Their α-Methyl Counterparts
  作者：Eyleen Alicea-Matías、John A. Soderquist

  DOI：10.1021/acs.orglett.6b03506

  日期：2017.1.20

  Available in either enantiomerically pure form through quantitative Grignard procedures from air-stable crystalline complexes (1, 3), the B-γ-TMS propargylic derivatives of the 10-TMS- (2) and 10-phenyl-9-borabicyclo[3.3.2]decanes (4) provide highly selective entries to 2°-allenyl carbinamines (8, 60–85%, 78–99% ee) and their 3° counterparts (13, 62–82%, 95–99% ee) through their additions to aldimines

  通过从空气稳定的结晶复合物（定量格利雅程序可用在任一对映体纯的形式1，3）时，乙-γ-TMS 10 TMS-（的炔衍生物2）和10-苯基-9-硼二环[3.3。 2]癸烷（4）提供高度选择性的条目，以2°-allenyl carbinamines（8，60-85％，78-99％ee）和它们的3°同行（13，62-82％，95-99％ee）的通过它们分别添加到醛亚胺和酮亚胺中。这些胺的绝对构型是通过8e的臭氧分解反应从已知的氨基酸衍生物16e R和19d R获得的R和13d R以及14f R的单晶X射线结构。
• Asymmetric Synthesis of Allyl- and α-Allenylamines from Chiral Imines and Alkynes via (η²-Imine)Ti(O-<i>i</i>-Pr)₂ Complexes
  作者：Kohki Fukuhara、Sentaro Okamoto、Fumie Sato

  DOI：10.1021/ol034599u

  日期：2003.6.1

  [GRAPHICS]The reaction of a divalent titanium reagent Ti(O-1-Pr)(4)/2i-PrMgX with optically active arylaidimines derived from arylaidehydes and O-methylphenylglycinol provided, in a highly diastereoselective manner, chiral (eta(2)-imine)Ti(O-i-Pr)(2) complexes, which in turn reacted with 1-alkynes or propargyl compounds to give optically active allyl- and alpha-allenylamines, respectively.