(1R,2S)-2-[methyl(prop-2-enyl)amino]-1-phenylpropan-1-ol | 150339-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S)-2-[methyl(prop-2-enyl)amino]-1-phenylpropan-1-ol
• CAS: 150339-21-2
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: YGTXXDWODIVLCZ-AAEUAGOBSA-N

物化性质

• 沸点：
  308.0±30.0 °C(predicted)
• 密度：
  0.997±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-[methyl(prop-2-enyl)amino]-1-phenylpropan-1-ol 在 lithium tetrachloropalladate 、 三氟乙酸 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 (2R,3S,6R)-6-(chloromethyl)-3,4-dimethyl-2-phenylmorpholine
  参考文献：
  名称：

  Stereochemistry and regiochemistry of heteroatom directed reactions. Part 4. Palladium(II)-catalyzed synthesis of optically active tetrahydro-1,4-oxazine derivatives

  摘要：

  Three different types of morpholine derivatives 1-3 could be obtained from allylic amine substrates 4 in high yield and excellent diastereoselectivity by slight, variation of the Pd(II)-Cu(II) reagents system.

  DOI：

  10.1021/jo00070a001
• 作为产物：
  描述：

  麻黄碱 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (1R,2S)-2-[methyl(prop-2-enyl)amino]-1-phenylpropan-1-ol
  参考文献：
  名称：

  Stereochemistry and regiochemistry of heteroatom directed reactions. Part 4. Palladium(II)-catalyzed synthesis of optically active tetrahydro-1,4-oxazine derivatives

  摘要：

  Three different types of morpholine derivatives 1-3 could be obtained from allylic amine substrates 4 in high yield and excellent diastereoselectivity by slight, variation of the Pd(II)-Cu(II) reagents system.

  DOI：

  10.1021/jo00070a001

文献信息

• Pd-Catalyzed Decarboxylative Asymmetric Protonation of Sterically Hindered α-Aryl Lactones and Dihydrocoumarins
  作者：Jinju James、Ramulu Akula、Patrick J. Guiry

  DOI：10.1002/adsc.201800724

  日期：2018.8.17

  Pd‐catalyzed decarboxylative asymmetric protonation (DAP) has been developed for sterically hindered α‐aryl lactone and dihydrocoumarin substrates. Optimization studies were conducted using δ‐lactone‐ and dihydrocoumarin‐derived α‐aryl, β‐oxo‐allyl esters with 2,4,6‐trimethoxyphenyl as the aryl substituent. In the absence of a chiral P,N‐ligand, (1R,2S)‐(−)ephedrine, a cheap and readily available chiral

  钯催化的脱羧不对称质子化（DAP）已开发用于空间受阻的α-芳基内酯和二氢香豆素底物。使用由δ-内酯和二氢香豆素衍生的α-芳基，β-氧代烯丙基酯与2,4,6-三甲氧基苯基作为芳基取代基进行了优化研究。在没有手性P，N-配体的情况下，（1 R，2 S）-（-）麻黄碱（廉价且容易获得的手性质子供体）与内酯和二氢香豆素的对映选择性高达92％ee和88％ee基板。含双邻位的庞大芳基取代基和萘基的对映选择性最高，分别高达92％和86％。提出了立体化学原理来解释不对称诱导的优选含义。
• Stereochemistry and regiochemistry of heteroatom directed reactions. Part 4. Palladium(II)-catalyzed synthesis of optically active tetrahydro-1,4-oxazine derivatives
  作者：Jinyu Lai、Xiaoxin Shi、Yanshen Gong、Lixin Dai

  DOI：10.1021/jo00070a001

  日期：1993.8

  Three different types of morpholine derivatives 1-3 could be obtained from allylic amine substrates 4 in high yield and excellent diastereoselectivity by slight, variation of the Pd(II)-Cu(II) reagents system.