(S,E)-N-苄基-(1-甲基-2-丁烯基)胺 | 121440-83-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S,E)-N-苄基-(1-甲基-2-丁烯基)胺
• 英文名称: (S,E)-N-benzyl-2-pent-3-enylamine
• 英文别名: (S,E)-N-benzyl-(1-methyl-2-butenyl)amine；(E,2S)-N-benzylpent-3-en-2-amine
• CAS: 121440-83-3
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: MMIOBUCKGJTLLY-KTROKBFUSA-N

物化性质

• 沸点：
  253.3±9.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-甲基羟胺盐酸盐 、 (S,E)-N-苄基-(1-甲基-2-丁烯基)胺 在 sodium tetrahydroborate 、 potassium carbonate 、 nickel dichloride 作用下， 生成 (2S,3S)-2-N-benzyl-3-N-methylpentane-2,3-diamine
  参考文献：
  名称：

  Factors influencing the reverse-Cope approach to 1,2,5-oxadiazinanes from allylamines and nitrones: Optimization of a new vicinal diamine synthesis

  摘要：

  Nitrones generated from formaldehyde and N-alkyl-hydroxylamines are particularly suitable reactants in tandem reverse-Cope-Meisenheimer reactions leading to oxadiazinanes and thence N-hydroxydiamines and vicinal diamines, front allylamines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10243-x
• 作为产物：
  描述：

  3-penten-2-ol 在 [(η³-allyl)Pd((S)-2-Ph2P-2'-Ph2P(S)-1,1'-binaphthyl)]SbF6 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 22.0h， 生成 (S,E)-N-苄基-(1-甲基-2-丁烯基)胺
  参考文献：
  名称：

  钯/ BINAP（S）催化的不对称烯丙基胺化。

  摘要：

  研究了钯/（S）-BINAP（S）体系催化的无环烯丙基碳酸酯的对映选择性烯丙基胺化。几种底物的胺化以高ee进行。碳酸巴豆酯显示对支链异构体的异常高的区域选择性。发现使用（S）-TolBINAP（S）和（S）-3,5-二甲苯基-BINAP（S）作为配体可增加胺的对映选择性。在X射线晶体学研究中发现BINAP（S）配体的AP，S结合模式。[反应：看文字]

  DOI：

  10.1021/ol047624k

文献信息

• Asymmetric allylic substitution reaction with nitrogen and oxygen nucleophiles using monodentate chiral phosphine, 9-PBN
  作者：Yasumasa Hamada、Noriko Seto、Yoshie Takayanagi、Takeshi Nakano、Osamu Hara

  DOI：10.1016/s0040-4039(99)01617-2

  日期：1999.10

  Asymmetric allylic substitution reactions between 1,3-diphenyl-2-propenyl acetate and various hetero nucleophiles were efficiently carried out using the catalysts derived from the monodentate phosphine ligands, (1R, 2S, 5R, 6S)-2,6-dimethyl-9-phenyl-9-phosphabicyclo[3.3.1] nonane and its enantiomer ((−)- and (+)-9-PBNs), and palladium (0).

  使用衍生自单齿膦配体（1 R，2 S，5 R，6 S）-2,6的催化剂，可以有效地进行1,3-二苯基-2-丙烯基乙酸丙烯酯与各种杂亲核试剂之间的不对称烯丙基取代反应-二甲基-9-苯基-9-磷酸双环[3.3.1]壬烷及其对映异构体（（-）-和（+）-9-PBNs）和钯（0）。
• Asymmetric synthesis catalyzed by chiral ferrocenylphosphine - transition-metal complexes. 8. Palladium-catalyzed asymmetric allylic amination
  作者：Tamio Hayashi、Akihiro Yamamoto、Yoshihiko Ito、Eriko Nishioka、Hitoshi Miura、Kazunori Yanagi

  DOI：10.1021/ja00198a048

  日期：1989.8
• A Widely Applicable Chiral Auxiliary, <i>cis</i>-2-Amino-3,3-dimethyl-1-indanol:  Conversion to a Novel Phosphorus-Containing Oxazoline and Its Application as a Highly Efficient Ligand for the Palladium-Catalyzed Enantioselective Allylic Amination Reaction
  作者：Atsushi Sudo、Kazuhiko Saigo

  DOI：10.1021/jo970359e

  日期：1997.8.1

  A chiral amino alcohol, cis-2-amino-3,3-dimethyl-1-indanol (2), was converted into the corresponding enantiomerically pure phosphorus-containing oxazoline 4. Oxazoline 4 was found to be an efficient ligand for palladium-catalyzed enantioselective allylic amination reactions: In the amination reaction of (E)-1,3-diphenyl-2-propen-1-yl acetate (7a), 4 was found to be more efficient than the similar ligands 1a-c, derived from valinol, tert-leucinol, etc. Other 1,3-bis(p-substituted aryl)-2-propen-1-yl acetates were also converted to the corresponding amines in a similar manner and with excellent enantioselectivity. In the amination reaction of 1-alkyl-3,3-diphenyl-2-propen-1-yl acetates 11, the correponding amines 12 were obtained with excellent enantioselectivity when acetic acid was added to the reaction system.
• Palladium/BINAP(S)-Catalyzed Asymmetric Allylic Amination
  作者：J. W. Faller、Jeremy C. Wilt

  DOI：10.1021/ol047624k

  日期：2005.2.1

  enantioselective allylic amination of acyclic allylic carbonates catalyzed by a palladium/(S)-BINAP(S) system was investigated. Amination of several substrates proceeded with high ee. Crotyl carbonates show an unusually high regioselectivity for the branched isomer. The use of (S)-TolBINAP(S) and (S)-3,5-xylyl-BINAP(S) as ligands was found to increase the enantioselectivity of the aminations. A P,S binding

  研究了钯/（S）-BINAP（S）体系催化的无环烯丙基碳酸酯的对映选择性烯丙基胺化。几种底物的胺化以高ee进行。碳酸巴豆酯显示对支链异构体的异常高的区域选择性。发现使用（S）-TolBINAP（S）和（S）-3,5-二甲苯基-BINAP（S）作为配体可增加胺的对映选择性。在X射线晶体学研究中发现BINAP（S）配体的AP，S结合模式。[反应：看文字]
• Factors influencing the reverse-Cope approach to 1,2,5-oxadiazinanes from allylamines and nitrones: Optimization of a new vicinal diamine synthesis
  作者：Kathryn E. Bell、Michael P. Coogan、Michael B. Gravestock、David W. Knight、Steven R. Thornton

  DOI：10.1016/s0040-4039(97)10243-x

  日期：1997.12

  Nitrones generated from formaldehyde and N-alkyl-hydroxylamines are particularly suitable reactants in tandem reverse-Cope-Meisenheimer reactions leading to oxadiazinanes and thence N-hydroxydiamines and vicinal diamines, front allylamines. (C) 1997 Elsevier Science Ltd.