ethyl (2R,3R)-2-azido-3-(4-chlorophenyl)-3-hydroxypropanoate | 299179-26-3

• 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: ethyl (2R,3R)-2-azido-3-(4-chlorophenyl)-3-hydroxypropanoate
• CAS: 299179-26-3
• 化学式: C₁₁H₁₂ClN₃O₃
• 分子量: 269.688
• InChiKey: AQRBZEAUQLCCRO-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (2R,3R)-2-azido-3-(4-chlorophenyl)-3-hydroxypropanoate 在 tin(ll) chloride 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 ethyl (2R,3R)-2-amino-3-(4-chlorophenyl)-3-hydroxypropanoate
  参考文献：
  名称：

  Synthetic studies on the DEF ring system of ristocetin A via ruthenium-promoted SNAr reaction: problems and solutions using arylserine–Ru complexes

  摘要：

  Ruthenium-promoted intramolecular SNAr reaction has allowed the construction of the 16-membered DEF model macrocycle of ristocetin A that incorporates the required arylserine residue as the E ring. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00855-8
• 作为产物：
  描述：

  对氯肉桂酸 在 sodium azide 、 甲基磺酰胺 、 AD-mix-β 、 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 65.0h， 生成 ethyl (2R,3R)-2-azido-3-(4-chlorophenyl)-3-hydroxypropanoate
  参考文献：
  名称：

  Synthetic studies on the DEF ring system of ristocetin A via ruthenium-promoted SNAr reaction: problems and solutions using arylserine–Ru complexes

  摘要：

  Ruthenium-promoted intramolecular SNAr reaction has allowed the construction of the 16-membered DEF model macrocycle of ristocetin A that incorporates the required arylserine residue as the E ring. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00855-8

文献信息

• Synthesis of a Key Precursor for Orienticin C and Model Study on Ruthenium-Mediated Macrocyclization
  作者：Anthony J. Pearson、Diana V. Ciurea

  DOI：10.1021/jo702245z

  日期：2008.1.1

  [GRAPHICS]A tripeptido-arene-ruthenium complex was prepared as a key precursor for the projected synthesis of orienticin C, demonstrating that the cyclopentadienylruthenium moiety can be attached to a chloroarene in the presence of multiple functionality. The ruthenium-mediated intramolecular SNAr reaction for formation of the required diaryl ether linkage was successfully tested on a model system.
• Synthetic studies on the DEF ring system of ristocetin A via ruthenium-promoted SNAr reaction: problems and solutions using arylserine–Ru complexes
  作者：Anthony J Pearson、Jung-Nyoung Heo

  DOI：10.1016/s0040-4039(00)00855-8

  日期：2000.8

  Ruthenium-promoted intramolecular SNAr reaction has allowed the construction of the 16-membered DEF model macrocycle of ristocetin A that incorporates the required arylserine residue as the E ring. (C) 2000 Elsevier Science Ltd. All rights reserved.