(1R*,2S*)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylic acid | 870288-18-9

• 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: (1R*,2S*)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylic acid
• 英文别名: rac,cis-2-(tert-butoxycarbonylamino)-cyclohex-3-ene carboxylic acid；2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylic acid；(1S,2R)-Boc-2-aminocyclohex-3-ene-carboxylic acid；(1S,2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]cyclohex-3-ene-1-carboxylic acid
• CAS: 870288-18-9
• 化学式: C₁₂H₁₉NO₄
• 分子量: 241.287
• InChiKey: QWRRLPZJKAWOFL-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R*,2S*)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylic acid 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.83h， 生成 cis-2-aminocyclohex-3-ene-1-carboxylic acid
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and X-ray Crystallography of a High-Affinity Antagonist of the Grb2-SH2 Domain Containing an Asparagine Mimetic

  摘要：

  Previous efforts in the search for molecules capable of blocking the associations between the activated tyrosine kinase growth factor receptors and the SH2 domain of Grb2 had resulted in the identification of 3-amino-Z-pTyr-Ac(6)c-Asn-NH2, a high-affinity and selective antagonist of this SH2 domain. In the present paper, we report the successful replacement of asparagine in this compound by a beta-amino acid mimetic, which brings us closer to our objective of identifying a Grb2-SH2 antagonist suitable for pharmacological investigations.

  DOI：

  10.1021/jm991013u
• 作为产物：
  描述：

  rac,cis-N-tert-butoxycarbonyl-7-azabicyclo<4.2.0>-oct-4-en-8-one 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以91%的产率得到(1R*,2S*)-2-(tert-butoxycarbonylamino)cyclohex-3-enecarboxylic acid
  参考文献：
  名称：

  Structure-Based Design, Synthesis, and X-ray Crystallography of a High-Affinity Antagonist of the Grb2-SH2 Domain Containing an Asparagine Mimetic

  摘要：

  Previous efforts in the search for molecules capable of blocking the associations between the activated tyrosine kinase growth factor receptors and the SH2 domain of Grb2 had resulted in the identification of 3-amino-Z-pTyr-Ac(6)c-Asn-NH2, a high-affinity and selective antagonist of this SH2 domain. In the present paper, we report the successful replacement of asparagine in this compound by a beta-amino acid mimetic, which brings us closer to our objective of identifying a Grb2-SH2 antagonist suitable for pharmacological investigations.

  DOI：

  10.1021/jm991013u

文献信息

• Stereo- and Regiocontrolled Syntheses of Exomethylenic Cyclohexane β-Amino Acid Derivatives
  作者：Loránd Kiss、Enikő Forró、György Orsy、Renáta Ábrahámi、Ferenc Fülöp

  DOI：10.3390/molecules201219749

  日期：——

  Cyclohexane analogues of the antifungal icofungipen [(1R,2S)-2-amino-4-methylenecyclopentanecarboxylic acid] were selectively synthesized from unsaturated bicyclic β-lactams by transformation of the ring olefinic bond through three different regio- and stereocontrolled hydroxylation techniques, followed by hydroxy group oxidation and oxo-methylene interconversion with a phosphorane. Starting from an

  通过三种不同的区域和立体控制羟基化技术，通过环烯烃键的转化，从不饱和双环β-内酰胺选择性地合成了抗真菌剂icofungipen [（1R，2S）-2-氨基-4-亚甲基环戊烷羧酸]的环己烷类似物羟基氧化和氧代亚甲基与磷烷的相互转化。从通过消旋外消旋化合物的酶促拆分获得的对映体纯的双环β-内酰胺开始，对映发散的方法导致制备了艾可芬净的右旋和左旋环己烷类似物。
• Regio- and diastereoselective fluorination of alicyclic β-amino acids
  作者：Loránd Kiss、Enikő Forró、Santos Fustero、Ferenc Fülöp

  DOI：10.1039/c1ob05648d

  日期：——

  A regio- and stereoselective approach to fluorinated β-aminocyclohexene or cyclohexane esters has been developed, starting from a bicyclic β-lactam (1). The procedure involves six or seven steps, based on regio- and stereoselective iodolactonization, lactone opening and hydroxy–fluorine exchange. The method has been extended to the synthesis of fluorinated amino ester enantiomers.

  从双环β-内酰胺（1）开始，已经开发了对氟代β-氨基环己烯或环己烷酯的区域和立体选择性方法。该过程包括六个或七个步骤，基于区域和立体选择性的碘内酯化，内酯开放和羟基-氟交换。该方法已扩展到氟化氨基酯对映体的合成。
• Synthesis of 3- and 4-Hydroxy-2-aminocyclohexanecarboxylic Acids by Iodocyclization
  作者：Zsolt Szakonyi、Szilvia Gyónfalvi、Enikö Forró、Anasztázia Hetényi、Norbert De Kimpe、Ferenc Fülöp

  DOI：10.1002/ejoc.200500297

  日期：2005.9

  novel routes have been developed for the synthesis of 2-amino-4-hydroxycyclohexanecarboxylic acid and its 3-hydroxy-substituted analog via iodooxazine, iodooxazoline or iodolactone intermediates. After CAL-B-catalyzed enzymatic transformation of the starting β-lactam, the iodolactone method was applied to the synthesis of 3-hydroxy-substituted β-amino acid enantiomers. (© Wiley-VCH Verlag GmbH & Co

  从 cis-7-azabicyclo[4.2.0]oct-4-en-8-one 开始，已经开发了通过碘恶嗪合成 2-氨基-4-羟基环己烷甲酸及其 3-羟基取代的类似物的新路线，碘恶唑啉或碘内酯中间体。在 CAL-B 催化酶促转化起始 β-内酰胺后，碘内酯法用于合成 3-羟基取代的 β-氨基酸对映异构体。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Structure-Based Design, Synthesis, and X-ray Crystallography of a High-Affinity Antagonist of the Grb2-SH2 Domain Containing an Asparagine Mimetic
  作者：Pascal Furet、Carlos García-Echeverría、Brigitte Gay、Joseph Schoepfer、Martin Zeller、Joseph Rahuel

  DOI：10.1021/jm991013u

  日期：1999.7.1

  Previous efforts in the search for molecules capable of blocking the associations between the activated tyrosine kinase growth factor receptors and the SH2 domain of Grb2 had resulted in the identification of 3-amino-Z-pTyr-Ac(6)c-Asn-NH2, a high-affinity and selective antagonist of this SH2 domain. In the present paper, we report the successful replacement of asparagine in this compound by a beta-amino acid mimetic, which brings us closer to our objective of identifying a Grb2-SH2 antagonist suitable for pharmacological investigations.