(E)-N-(tert-butoxycarbonyl)-2-amino-4-methoxy-3-butene | 124754-96-7

• 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: (E)-N-(tert-butoxycarbonyl)-2-amino-4-methoxy-3-butene
• 英文别名: tert-butyl N-[(E,2S)-4-methoxy-1-phenylbut-3-en-2-yl]carbamate
• CAS: 124754-96-7
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: OPBCZNSKHPCCDQ-PLSXKVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-N-(tert-butoxycarbonyl)-2-amino-4-methoxy-3-butene 在 titanium(IV) isopropylate 、 sodium tetrahydroborate 、 sodium carbonate 、 lithium chloride 作用下， 以 乙醇 、 水 为溶剂， 生成 (1-benzyl-3-hydroxy-2-phenylselanyl-propyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  苯硒基氯的立体选择性加成到衍生自N-保护的手性α-氨基酸的甲氧基烯烃中。

  摘要：

  衍生自N-Boc或N-Cbzα-氨基酸的（E）-甲氧基烯烃在Ti（O i -Pr）4和LiCl的存在下进行立体选择性加成的苯基硒基氯，得到相应的苯基硒基醛，可以很容易地转化为含有氮丙啶环的新对映体纯氨基酸。

  DOI：

  10.1016/s0040-4039(99)00761-3
• 作为产物：
  描述：

  N-Boc-L-苯丙氨醛 、 甲氧基甲基三苯基氯化膦 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (Z)-N-(tert-butoxycarbonyl)-2-amino-4-methoxy-3-butene 、 (E)-N-(tert-butoxycarbonyl)-2-amino-4-methoxy-3-butene
  参考文献：
  名称：

  Diastereoselectivity of Additions to Chiral Carbonyl Oxides

  摘要：

  The influence of a resident stereocenter on the formation of hydroperoxy acetals from carbonyl oxides is investigated. Addition of either methanol or 2-propanol to 8-phenylpropanal O-oxide proceeds with modest stereoselectivity; addition of a tertiary alcohol proceeds with higher selectivity. Product stereochemistry, which is confirmed by conversion of a functionalized hydroperoxy acetal to a 1,2-dioxane, is found to derive from nucleophilic attack through a Felkin-Anh type transition state. Trapping of a carbonyl oxide containing a neighboring hydrogen bond donor proceeds with modest selectivity for both syn- and anti-carbonyl oxide isomers. Ozonolysis of a 3-(trialkylstannyl)-1-enol ether proceeds with loss of the stannyl-bearing carbon through the possible intermediacy of a vinyl peroxide.

  DOI：

  10.1021/jo00130a021

文献信息

• Diastereoselectivity of Additions to Chiral Carbonyl Oxides
  作者：Patrick H. Dussault、Umesh R. Zope

  DOI：10.1021/jo00130a021

  日期：1995.12

  The influence of a resident stereocenter on the formation of hydroperoxy acetals from carbonyl oxides is investigated. Addition of either methanol or 2-propanol to 8-phenylpropanal O-oxide proceeds with modest stereoselectivity; addition of a tertiary alcohol proceeds with higher selectivity. Product stereochemistry, which is confirmed by conversion of a functionalized hydroperoxy acetal to a 1,2-dioxane, is found to derive from nucleophilic attack through a Felkin-Anh type transition state. Trapping of a carbonyl oxide containing a neighboring hydrogen bond donor proceeds with modest selectivity for both syn- and anti-carbonyl oxide isomers. Ozonolysis of a 3-(trialkylstannyl)-1-enol ether proceeds with loss of the stannyl-bearing carbon through the possible intermediacy of a vinyl peroxide.
• Stereoselective addition of phenyl selenyl chloride to methoxy alkenes derived from N-protected chiral α-amino acids.
  作者：Mariangela Demarcus、Silvia N. Filigheddu、André Mann、Maurizio Taddei

  DOI：10.1016/s0040-4039(99)00761-3

  日期：1999.6

  (E)-Methoxy alkenes derived from N-Boc or N-Cbz α-amino acids undergo stereoselective addition of phenyl selenyl chloride in the presence of Ti(Oi-Pr)4 and LiCl to give the corresponding phenylselenyl aldehydes that can be easily transformed into new enantiomerically pure amino acids containing an aziridine ring.

  衍生自N-Boc或N-Cbzα-氨基酸的（E）-甲氧基烯烃在Ti（O i -Pr）4和LiCl的存在下进行立体选择性加成的苯基硒基氯，得到相应的苯基硒基醛，可以很容易地转化为含有氮丙啶环的新对映体纯氨基酸。