2-乙酰氨基-2-氯乙酸乙酯 | 819877-81-1

• 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
• 中文名称: 2-乙酰氨基-2-氯乙酸乙酯
• 英文名称: Ethyl 2-chloro-2-acetamidoacetate
• 英文别名: ethyl 2-acetamido-2-chloroacetate
• CAS: 819877-81-1
• 化学式: C₆H₁₀ClNO₃
• 分子量: 179.603
• InChiKey: CHYHOSYHUSIVCU-UHFFFAOYSA-N

物化性质

• 沸点：
  283.2±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异腈基正丁烷 、 2-乙酰氨基-2-氯乙酸乙酯 在 二甲基氯化铝 作用下， 以 四氢呋喃 、 hexanes 为溶剂， 反应 24.0h， 以52%的产率得到ethyl 5-(butylamino)-2-methyloxazole-4-carboxylate
  参考文献：
  名称：

  Synthesis of 5-Amino-oxazole-4-carboxylates from α-Chloroglycinates

  摘要：

  Aluminum-based Lewis acids are effective promoters of the condensation of alpha-chloroglycinates with isonitriles or with cyanide ion, leading to the formation of 5-amino-oxazoles.

  DOI：

  10.1021/ol101704r
• 作为产物：
  描述：

  acetylaminohydroxyacetic acid ethyl ester 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2-乙酰氨基-2-氯乙酸乙酯
  参考文献：
  名称：

  恶唑类结合剂的研制及其在全合成虹吸管中的应用

  摘要：

  描述了4-碳乙氧基-5-甲基-2-（苯磺酰基）甲基恶唑的制备及其在制备更复杂的恶唑中的用途。独特的天然产物虹吸管A和B的全合成说明了该构件的应用。还介绍了虹吸管的生物活性。

  DOI：

  10.1021/jo9018705

文献信息

• Development of an Oxazole Conjunctive Reagent and Application to the Total Synthesis of Siphonazoles
  作者：Jianmin Zhang、Elena A. Polishchuk、Jie Chen、Marco A. Ciufolini

  DOI：10.1021/jo9018705

  日期：2009.12.4

  The preparation of 4-carbethoxy-5-methyl-2-(phenylsulfonyl)methyloxazole and its use in the elaboration of more complex oxazoles are described. A total synthesis of the unique natural products siphonazoles A and B, illustrates an application of this building block. A discussion of the biological activity of the siphonazoles is also presented.

  描述了4-碳乙氧基-5-甲基-2-（苯磺酰基）甲基恶唑的制备及其在制备更复杂的恶唑中的用途。独特的天然产物虹吸管A和B的全合成说明了该构件的应用。还介绍了虹吸管的生物活性。
• A Practical Preparation of Ethyl<i>N</i>-Acyl-2-(dimethoxyphosphoryl)glycinate
  作者：Feng Xu、Paul Devine

  DOI：10.1021/op1000594

  日期：2010.5.21

  A practical, cost-effective preparation of ethyl N-acyl-2-(dimethoxyphosphoryl)glycinate has been developed. The two-step process achieved an 80% overall isolated yield.
• A Peterson avenue to 5-alkenyloxazoles
  作者：Jaclyn Chau、Jianmin Zhang、Marco A. Ciufolini

  DOI：10.1016/j.tetlet.2009.08.076

  日期：2009.11

  The TiCl4-promoted Peterson olefination of aldehydes with readily available 5-(trimethylsilyl)methyloxazoles furnishes 5-alkenyloxazoles (mostly E-isomers). (C) 2009 Elsevier Ltd. All rights reserved.
• Asymmetric Mannich Synthesis of α-Amino Esters by Anion-Binding Catalysis
  作者：Masayuki Wasa、Richard Y. Liu、Stéphane P. Roche、Eric N. Jacobsen

  DOI：10.1021/ja5075163

  日期：2014.9.17

  We report a scalable, one-pot Mannich route to enantioenriched α-amino esters by direct reaction of α-chloroglycine ester as a practical imino ester surrogate. The reaction is promoted by a chiral aminothiourea, which is proposed to operate cooperatively by generating an iminium ion by chloride abstraction and an enolate by deprotonation, followed by highly stereoselective C-C bond formation between both reactive intermediates associated non-covalently within the catalyst framework.
• Synthesis of 5-Amino-oxazole-4-carboxylates from α-Chloroglycinates
  作者：Jianmin Zhang、Pierre-Yves Coqueron、Jean-Pierre Vors、Marco A. Ciufolini

  DOI：10.1021/ol101704r

  日期：2010.9.3

  Aluminum-based Lewis acids are effective promoters of the condensation of alpha-chloroglycinates with isonitriles or with cyanide ion, leading to the formation of 5-amino-oxazoles.