(4-isopropyl-benzylidene)-((R)-1-phenyl-ethyl)-amine | 4187-49-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4-isopropyl-benzylidene)-((R)-1-phenyl-ethyl)-amine
• 英文别名: (4-Isopropyl-benzyliden)-((R)-1-phenyl-aethyl)-amin；4-Isopropyl-benzaldehyd-((R)-1-phenyl-aethylimin)；N-[(1R)-1-phenylethyl]-1-(4-propan-2-ylphenyl)methanimine
• CAS: 4187-49-9；88644-93-3
• 化学式: C₁₈H₂₁N
• 分子量: 251.371
• InChiKey: KHZHAVNBYVWNHS-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  R_P-(-)-menthyl phenylphosphine oxide 、 (4-isopropyl-benzylidene)-((R)-1-phenyl-ethyl)-amine 以 neat (no solvent) 为溶剂， 反应 12.0h， 以56%的产率得到(Rp)-(-)-menthyl(phenyl)[(R)-N-(R)-1-phenylethylamino-p-i-propylbenzyl]phosphine oxide
  参考文献：
  名称：

  （RP）-甲基苯基膦氧化物加到手性醛亚胺中的双重不对称诱导。

  摘要：

  在纯净条件下于80°C于最高91：9 dr C和99％的收率下，通过向手性醛亚胺中添加（R P）-薄荷基苯基膦氧化物制备P，C-立体异构α-氨基膦氧化物。非对映选择性主要是由手性磷诱导的，它们分别与（S）-或（R）-亚胺形成匹配或不匹配的诱导。手性28：132–135，2016。©2015 Wiley Periodicals，Inc.

  DOI：

  10.1002/chir.22549
• 作为产物：
  描述：

  R(+)-alpha-甲基苄胺 、 4-异丙基苯甲醛 以 乙醇 为溶剂， 反应 6.0h， 生成 (4-isopropyl-benzylidene)-((R)-1-phenyl-ethyl)-amine
  参考文献：
  名称：

  Asymmetric induction in the addition of enantiomerically pure H -phosphinate to chiral aldimines: diastereoselective generation of α-amino phosphinates with P , C -stereogenic centers

  摘要：

  alpha-Amino phosphinates with P,C-stereogenic centers were prepared from a P-retained addition of (R-p)-(-)-menthyl H-phenylphosphinate to (R)-aldimines with up to 86:14 dr under catalyst and solvent free condition at ambient temperature; the single (S-p,S alpha-c)-stereoisomers were isolated in moderate yields. Chirality on the nitrogen of chiral aldimine was proposed to control the stereoselectivity, and the (-)-menthoxyl showed mismatched asymmetric induction with (S)-aldimines. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.06.022

文献信息

• Asymmetric induction in the addition of enantiomerically pure H -phosphinate to chiral aldimines: diastereoselective generation of α-amino phosphinates with P , C -stereogenic centers
  作者：Meng Yang、Hao Xu、Zhong-Yang Zhou、He Zhang、Li-Juan Liu、Yong-Ming Sun、Shao-Zhen Nie、Chang-Qiu Zhao

  DOI：10.1016/j.tetasy.2016.06.022

  日期：2016.10

  alpha-Amino phosphinates with P,C-stereogenic centers were prepared from a P-retained addition of (R-p)-(-)-menthyl H-phenylphosphinate to (R)-aldimines with up to 86:14 dr under catalyst and solvent free condition at ambient temperature; the single (S-p,S alpha-c)-stereoisomers were isolated in moderate yields. Chirality on the nitrogen of chiral aldimine was proposed to control the stereoselectivity, and the (-)-menthoxyl showed mismatched asymmetric induction with (S)-aldimines. (C) 2016 Elsevier Ltd. All rights reserved.
• Double Asymmetric Induction During the Addition of (<i>R</i>_P)-Menthyl Phenyl Phosphine Oxide to Chiral Aldimines
  作者：Zhong-Yang Zhou、He Zhang、Lan Yao、Jing-Hong Wen、Shao-Zhen Nie、Chang-Qiu Zhao

  DOI：10.1002/chir.22549

  日期：2016.2

  P,C‐Stereogenic α‐amino phosphine oxides were prepared from the addition of (RP)‐menthyl phenyl phosphine oxide to chiral aldimines under neat condition at 80 °C in up to 91:9 drC and 99% yields. The diastereoselectivity was mainly induced by chiral phosphorus that showed matched or mismatched induction with (S)‐ or (R)‐aldimines, respectively. Chirality 28:132–135, 2016. © 2015 Wiley Periodicals,

  在纯净条件下于80°C于最高91：9 dr C和99％的收率下，通过向手性醛亚胺中添加（R P）-薄荷基苯基膦氧化物制备P，C-立体异构α-氨基膦氧化物。非对映选择性主要是由手性磷诱导的，它们分别与（S）-或（R）-亚胺形成匹配或不匹配的诱导。手性28：132–135，2016。©2015 Wiley Periodicals，Inc.