(2Z)-(-)-methyl 2-methyl-3-[(R)-α-methylbenzylamino]-2-butenoate | 179320-79-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2Z)-(-)-methyl 2-methyl-3-[(R)-α-methylbenzylamino]-2-butenoate
• 英文别名: methyl (Z)-2-methyl-3-[[(1R)-1-phenylethyl]amino]but-2-enoate
• CAS: 179320-79-7
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: CQGFFOLNIFZJTI-NLYDNYMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2Z)-(-)-methyl 2-methyl-3-[(R)-α-methylbenzylamino]-2-butenoate 在 三乙酰氧基硼氢化钠 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 4.0h， 以54%的产率得到(2S,3R)-2-Methyl-3-((R)-1-phenyl-ethylamino)-butyric acid methyl ester
  参考文献：
  名称：

  Stereoselective Reduction of Enantiopure β-Enamino Esters by Hydride:  A Convenient Synthesis of Both Enantiopure β-Amino Esters

  摘要：

  The reduction of enantiopure beta-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo- and enantioselectivity to yield beta-amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is reported for the origin of the stereoselectivity through an enol ester-diacetoxyborohydride 6, which affords the intramolecular reduction. By choosing the appropriate chiral amine, this procedure allows a straightforward preparation of both the enantiopure beta-amino esters and derivatives with known biological activity, using readily available starting materials and inexpensive reagents and conditions.

  DOI：

  10.1021/jo960107y
• 作为产物：
  描述：

  2-甲基-3-氧代丁酸甲酯 、 R(+)-alpha-甲基苄胺 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以92%的产率得到(2Z)-(-)-methyl 2-methyl-3-[(R)-α-methylbenzylamino]-2-butenoate
  参考文献：
  名称：

  Maiti; Ghoshal; Mukhopadhyay, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1072 - 1080

  摘要：

  DOI：

文献信息

• Maiti; Ghoshal; Mukhopadhyay, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 11, p. 1072 - 1080
  作者：Maiti、Ghoshal、Mukhopadhyay、Achari、Banerjee

  DOI：——

  日期：——
• Stereoselective Reduction of Enantiopure β-Enamino Esters by Hydride:  A Convenient Synthesis of Both Enantiopure β-Amino Esters
  作者：Cristina Cimarelli、Gianni Palmieri

  DOI：10.1021/jo960107y

  日期：1996.1.1

  The reduction of enantiopure beta-enamino esters 1 with sodium triacetoxyborohydride in acetic acid is described. This occurs with good diastereo- and enantioselectivity to yield beta-amino esters 2 and 3 (after hydrogenolysis of the N-chiral group). A model is reported for the origin of the stereoselectivity through an enol ester-diacetoxyborohydride 6, which affords the intramolecular reduction. By choosing the appropriate chiral amine, this procedure allows a straightforward preparation of both the enantiopure beta-amino esters and derivatives with known biological activity, using readily available starting materials and inexpensive reagents and conditions.