ethyl (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylcyclobutane-1-carboxylate

• 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 (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylcyclobutane-1-carboxylate
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: XSSBKKOZZUHOEP-KDOFPFPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylcyclobutane-1-carboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 以90%的产率得到(1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylcyclobutane-1-carboxylic acid
  参考文献：
  名称：

  Synthesis of the four stereoisomers of cyclobutane analogues of phenylalanine in enantiomerically pure form

  摘要：

  All stereoisomers of 1-amino-2-phenylcyclobutanecarboxylic acid-c(4)Phe-have been synthesized and the series c(n)Phe has thus been completed. The use of two different strategies based on a cyclization reaction, starting from ethyl isocyanoacetate and dialkyl malonate, respectively, gave both cis-c(4)Phe and trans-c(4)Phe in racemic form. HPLC resolution of one of the intermediates using a cellulose-derived chiral stationary phase allowed the isolation of the corresponding enantiomerically pure N-protected amino acids, prepared for incorporation into peptides. The relative stereochemistry of enantiopure compounds has been unambiguously assigned. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.015
• 作为产物：
  描述：

  (1,3-二溴丙基)苯 在 盐酸 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 五氯化磷 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 154.5h， 生成 ethyl (1S,2R)-1-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylcyclobutane-1-carboxylate
  参考文献：
  名称：

  Synthesis of the four stereoisomers of cyclobutane analogues of phenylalanine in enantiomerically pure form

  摘要：

  All stereoisomers of 1-amino-2-phenylcyclobutanecarboxylic acid-c(4)Phe-have been synthesized and the series c(n)Phe has thus been completed. The use of two different strategies based on a cyclization reaction, starting from ethyl isocyanoacetate and dialkyl malonate, respectively, gave both cis-c(4)Phe and trans-c(4)Phe in racemic form. HPLC resolution of one of the intermediates using a cellulose-derived chiral stationary phase allowed the isolation of the corresponding enantiomerically pure N-protected amino acids, prepared for incorporation into peptides. The relative stereochemistry of enantiopure compounds has been unambiguously assigned. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.10.015

文献信息

• Synthesis and SAR of 2-phenyl-1-sulfonylaminocyclopropane carboxylates as ADAMTS-5 (Aggrecanase-2) inhibitors
  作者：Makoto Shiozaki、Hiroto Imai、Katsuya Maeda、Tomoya Miura、Katsutaka Yasue、Akira Suma、Masahiro Yokota、Yosuke Ogoshi、Julia Haas、Andrew M. Fryer、Ellen R. Laird、Nicole M. Littmann、Steven W. Andrews、John A. Josey、Takayuki Mimura、Yuichi Shinozaki、Hiromi Yoshiuchi、Takashi Inaba

  DOI：10.1016/j.bmcl.2009.08.093

  日期：2009.11

  A series of 1-sulfonylaminocyclopropanecarboxylates was synthesized as ADAMTS-5 (Aggrecanase-2) inhibitors. After an intensive investigation of the central cyclopropane core including its absolute stereochemistry and substituents, we found compound 22 with an Agg-2 IC(50) = 7.4 nM, the most potent ADAMTS-5 inhibitor reported so far. (c) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of the four stereoisomers of cyclobutane analogues of phenylalanine in enantiomerically pure form
  作者：Marta Lasa、Pilar López、Carlos Cativiela

  DOI：10.1016/j.tetasy.2005.10.015

  日期：2005.12

  All stereoisomers of 1-amino-2-phenylcyclobutanecarboxylic acid-c(4)Phe-have been synthesized and the series c(n)Phe has thus been completed. The use of two different strategies based on a cyclization reaction, starting from ethyl isocyanoacetate and dialkyl malonate, respectively, gave both cis-c(4)Phe and trans-c(4)Phe in racemic form. HPLC resolution of one of the intermediates using a cellulose-derived chiral stationary phase allowed the isolation of the corresponding enantiomerically pure N-protected amino acids, prepared for incorporation into peptides. The relative stereochemistry of enantiopure compounds has been unambiguously assigned. (c) 2005 Elsevier Ltd. All rights reserved.