tert-butyl 2-(2,2-dimethyl-1-phenylpropylideneamino)acetate | 1012085-18-5

• 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 2-(2,2-dimethyl-1-phenylpropylideneamino)acetate
• 英文别名: N-(tert-butylphenylmethylidene)glycine tert-butyl ester；Tert-butyl 2-[(2,2-dimethyl-1-phenylpropylidene)amino]acetate
• CAS: 1012085-18-5
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: SIACRHXLWVXCTH-UHFFFAOYSA-N

物化性质

• 沸点：
  334.4±34.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(2,2-dimethyl-1-phenylpropylideneamino)acetate 在 盐酸 、 calcium bis-iso-propoxide 、 碳酸氢钠 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 生成 (3R,4R)-5-(tert-butoxy)-4-((tert-butoxycarbonyl)amino)-3-methyl-5-oxopentanoic acid
  参考文献：
  名称：

  An Asymmetric Synthesis of l-Pyrrolysine

  摘要：

  An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.

  DOI：

  10.1021/ol300045c

文献信息

• Development of Catalytic Asymmetric 1,4-Addition and [3 + 2] Cycloaddition Reactions Using Chiral Calcium Complexes
  作者：Tetsu Tsubogo、Susumu Saito、Kazutaka Seki、Yasuhiro Yamashita、Shu̅ Kobayashi

  DOI：10.1021/ja8032058

  日期：2008.10.8

  4-addition and [3 + 2] cycloaddition reactions using chiral calcium species prepared from calcium isopropoxide and chiral bisoxazoline ligands have been developed. Glycine Schiff bases reacted with acrylic esters to afford 1,4-addition products, glutamic acid derivatives, in high yields with high enantioselectivities. During the investigation of the 1,4-addition reactions, we unexpectedly found that a [3

  已经开发了使用由异丙醇钙和手性双恶唑啉配体制备的手性钙物质的催化不对称 1,4-加成和 [3 + 2] 环加成反应。甘氨酸席夫碱与丙烯酸酯反应以高产率和高对映选择性提供 1,4-加成产物谷氨酸衍生物。在研究 1,4-加成反应期间，我们意外地发现 [3 + 2] 环加成发生在与巴豆酸酯衍生物的反应中，以高产率和高对映选择性提供取代的吡咯烷衍生物。基于这一发现，我们研究了不对称的 [3 + 2] 环加成，结果表明，获得了具有高非对映选择性和对映选择性的几种含有连续立体异构叔和季碳中心的旋光取代吡咯烷衍生物。此外，已经使用这种 [3 + 2] 环加成反应合成了丙型肝炎病毒 RNA 依赖性聚合酶抑制剂的光学活性吡咯烷核心和潜在的有效抗病毒剂。NMR 光谱分析和非线性效应实验中对映选择性的非放大观察表明，形成了具有阴离子配体的单体钙物质作为活性催化剂。提出了 [3 + 2] 环加成的逐步机制，包括 1
• Calcium-Catalyzed Diastereo- and Enantioselective 1,4-Addition of Glycine Derivatives to α,β-Unsaturated Esters
  作者：Shū Kobayashi、Tetsu Tsubogo、Susumu Saito、Yasuhiro Yamashita

  DOI：10.1021/ol702958w

  日期：2008.3.1

  4-addition reactions of a glycine Schiff base to beta-substituted alpha,beta-unsaturated esters have been developed. The reaction pathway was successfully controlled, and the desired 1,4-addition products were exclusively obtained with high enantioselectivities. The product obtained was converted to a 3-substituted glutamic acid derivative by acid hydrolysis.

  已经开发了甘氨酸席夫碱对β-取代的α，β-不饱和酯的第一个高度非对映和对映选择性的催化不对称1，4-加成反应。成功控制了反应路径，并且仅以高对映选择性获得了所需的1,4-加成产物。通过酸水解将获得的产物转化为3-取代的谷氨酸衍生物。
• An Asymmetric Synthesis of <scp>l</scp>-Pyrrolysine
  作者：Margaret L. Wong、Ilia A. Guzei、Laura L. Kiessling

  DOI：10.1021/ol300045c

  日期：2012.3.16

  An efficient asymmetric synthesis of the 22nd amino acid L-pyrrolysine has been accomplished. The key stereogenic centers were installed by an asymmetric conjugate addition reaction. A Staudinger/aza-Wittig cyclization was used to form the acid-sensitive pyrroline ring. Pyrrolysine was synthesized in 13 steps in 20% overall yield.