methyl (1S,6R)-6-isocyanatocyclohex-3-ene-1-carboxylate | 503167-42-8

• 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: methyl (1S,6R)-6-isocyanatocyclohex-3-ene-1-carboxylate
• CAS: 503167-42-8
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: ZFXOOUXMNWWYGS-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.83
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  55.73
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (1S,6R)-6-isocyanatocyclohex-3-ene-1-carboxylate 在 咪唑 、 sodium azide 、 碘 、 copper(II) bis(trifluoromethanesulfonate) 、 间氯过氧苯甲酸 、 copper(l) chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 60.0h， 生成 methyl (1S,2R,4R,5R)-4-(2-azidoethoxy)-2-(tert-butoxycarbonylamino)-5-(tert-butyldimethylsilanyloxy)cyclohexanecarboxylate
  参考文献：
  名称：

  2-Azidoethoxy derivatives of 2-aminocyclohexanecarboxylic acids (ACHC): interesting building blocks for the synthesis of cyclic β-peptide conjugates

  摘要：

  Oligomers of cyclic-beta-aminoacids possess a high resistance to peptidase-catalyzed hydrolysis and display a high intrinsic tendency to adopt regular secondary structures. These characteristics are attractive to develop new biologically active substances. However, cyclic-beta-peptides often show limited solubility in water and cannot be conjugated to biologically relevant fragments, such as oligosaccharides, which are often essential for full biological activity of natural alpha-peptides. In this article, we report the synthesis of one trans- and one cis-2-aminocyclohexanecarboxylic acid (ACHC), both functionalized with a hydroxy group, to increase the solubility in water, and an azidoethoxy group to allow the synthesis of cyclic-beta-peptide conjugates by a 'click reaction'. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.131
• 作为产物：
  描述：

  在 sodium azide 作用下， 生成 methyl (1S,6R)-6-isocyanatocyclohex-3-ene-1-carboxylate
  参考文献：
  名称：

  Diversified synthetic approaches to the carbapenem antibiotics based on symmetrization-asymmetrization concept

  摘要：

  DOI：

  10.1016/s0040-4039(00)98938-x

文献信息

• Chiral synthon obtained with pig liver esterase: Introduction of chiral centers into cyclohexene skeleton.
  作者：Susumu KOBAYASHI、Keiji KAMIYAMA、Masaji OHNO

  DOI：10.1248/cpb.38.350

  日期：——

  A versatile chiral synthon, (1R, 6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid, was obtained by an enantioselective ydrolysis of the corresponding meso diester with pig liver esterase. This enzymatic hydrolysis can easily be carried out on a multi-hundred gram scale. The chiral monoester thus obtained can be further converted into all stereoisomers of 1-amino-2-alkoxycarbonyl-4-cyclohexene derivatives in an enantio- and stereocontrolled manner. These derivatives are considered as potential key intermediates for synthesizing a variety of biologically interesting compounds such as aminocyclitol and carbapenem antibiotics.

  利用猪肝酯酶对相应的中二酯类进行对映选择性水解，获得了一种多功能手性合成物--(1R, 6S)-6-甲氧基羰基-3-环己烯-1-羧酸。这种酶水解可以在数百克的规模上轻松进行。由此获得的手性单酯可以对映和立体可控的方式进一步转化为 1-氨基-2-烷氧羰基-4-环己烯衍生物的所有立体异构体。这些衍生物被认为是潜在的关键中间体，可用于合成多种具有生物学意义的化合物，如氨基环糖醇和碳青霉烯类抗生素。
• Glycosidase antibodies induced to a half-chair transition-state analog
  作者：Hiroaki Suga、Norihiko Tanimoto、Anthony J. Sinskey、Satoru Masamune

  DOI：10.1021/ja00103a061

  日期：1994.11