tert-butyl (E)-(4-hydroxybut-2-en-1-yl)(methyl)carbamate | 149650-09-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (E)-(4-hydroxybut-2-en-1-yl)(methyl)carbamate
• 英文别名: N-tert-butyloxycarbonyl-4-methylamino-(E)-but-2-en-1-ol；Carbamic acid, (4-hydroxy-2-butenyl)methyl-, 1,1-dimethylethyl ester, (E)-；tert-butyl N-[(E)-4-hydroxybut-2-enyl]-N-methylcarbamate
• CAS: 149650-09-9
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: MGYQGBYAGILOSW-AATRIKPKSA-N

物化性质

• 沸点：
  291.1±29.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (E)-(4-hydroxybut-2-en-1-yl)(methyl)carbamate 在 水 、 sodium hexamethyldisilazane 、 四丁基碘化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 反应 16.0h， 生成 tert-butyl (Z)-buta-1,3-dien-1-yl(methyl)carbamate
  参考文献：
  名称：

  Stereoselective preparation of (1Z)- and (1E)-N-Boc-1-amino-1,3-dienes by stereospecific base-promoted 1,4-elimination

  摘要：

  The base-promoted 1,4-elimination reaction of N-Boc-1-amino-4-methoxy-2-alkene 1 is shown to proceed with perfect stereoselectivity to afford the corresponding N-Boc-1-amino-1,3-diene 2 in good yields. The reaction is highly stereospecific. The substrate E-1 gave 1Z-2 by the 'Syn-Effect' and Z-1 gave 1E-2 via formation of a chelated intermediate. Our method is widely applicable to the preparation of various types of N-Boc-1-amino-1,3-dienes 2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.039
• 作为产物：
  描述：

  氨甲酸,甲基-2-炔丙基-,1,1-二甲基乙基酯 在 正丁基锂 、 红铝 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 3.42h， 生成 tert-butyl (E)-(4-hydroxybut-2-en-1-yl)(methyl)carbamate
  参考文献：
  名称：

  Stereoselective preparation of (1Z)- and (1E)-N-Boc-1-amino-1,3-dienes by stereospecific base-promoted 1,4-elimination

  摘要：

  The base-promoted 1,4-elimination reaction of N-Boc-1-amino-4-methoxy-2-alkene 1 is shown to proceed with perfect stereoselectivity to afford the corresponding N-Boc-1-amino-1,3-diene 2 in good yields. The reaction is highly stereospecific. The substrate E-1 gave 1Z-2 by the 'Syn-Effect' and Z-1 gave 1E-2 via formation of a chelated intermediate. Our method is widely applicable to the preparation of various types of N-Boc-1-amino-1,3-dienes 2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.039

文献信息

• Applications of Organocatalytic Asymmetric Synthesis to Drug Prototypes—Dual Action and Selective Inhibitors of <i>n</i>-Nitric Oxide Synthase with Activity Against the 5-HT_1D/1B Subreceptors
  作者：Stephen Hanessian、Eli Stoffman、Xueling Mi、Paul Renton

  DOI：10.1021/ol102795g

  日期：2011.3.4

  The scope of MacMillan's organocatalytic asymmetric conjugate addition reaction of indoles and electron-rich aromatics to alpha,beta-unsaturated aldehydes has been extended to the use of 3-amino crotonaldehydes as substrates. The aromatics used include indoles as well as an aniline and a furan. The scope and effect of the groups on nitrogen (R, R') has also been studied. The method has been applied to the concise synthesis of an advanced precursor to S-(+)-1, a drug prototype for the treatment of migraine headaches.