trans-2-acetamidocyclohexyl acetate | 202461-26-5

• 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: trans-2-acetamidocyclohexyl acetate
• 英文别名: [(1S,2S)-2-acetamidocyclohexyl] acetate
• CAS: 202461-26-5
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: BVZMBDRGQAOJGO-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  trans-2-acetamidocyclohexyl acetate 在 盐酸 作用下， 反应 3.0h， 以97%的产率得到(1S,2S)-反式-2-氨基环己醇
  参考文献：
  名称：

  Asymmetric Acylation Reactions Catalyzed by Conformationally Biased Octapeptides

  摘要：

  Octapeptides capable of adopting P-hairpin conformations have been found to function as efficient catalysts for the kinetic resolution of certain racemic secondary alcohols. Parallel solid phase synthesis of a series of peptides with the common feature of the D-Pro-Gly sequence at the turn region (i+3 to i+4) was carried out to yield a family of octapeptide catalysts. The peptides were then screened for their efficiency in a number of enantioselective acylation reactions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00884-x
• 作为产物：
  描述：

  乙酸酐 、 (+/-)-(trans-2-hydroxy-cyclohexyl)-guanidine; sulfate 生成 trans-2-acetamidocyclohexyl acetate
  参考文献：
  名称：

  胍化合物：IV。一些烷基取代的胍与乙酸酐和乙酸乙酯的乙酰化

  摘要：

  使用乙酸乙酯和乙酸酐研究了一些单-、N,N- 和 N,N'-二烷基胍的乙酰化。除 N,N-二烷基胍外，乙酸乙酯对游离 b...

  DOI：

  10.1139/v61-126

文献信息

• Backbone Modification of β-Hairpin-Forming Tetrapeptides in Asymmetric Acyl Transfer Reactions
  作者：Peng Chen、Jin Qu

  DOI：10.1021/jo200403g

  日期：2011.5.6

  acyl transfer reaction of trans-2-(N-acetylamino)cyclohexan-1-ol (krel = 28). Through our backbone modification strategy, thioamide and sulfonamide as the isosteres of amide were introduced in the β-hairpin secondary structure. The thioxo peptides also adopt β-hairpin conformations as the oxopeptide supported by the combined use of NMR, IR, and X-ray techniques. Thioxo tetrapeptide 14 formed a more

  合成的寡肽作为酶的模拟物已被越来越多地用作不对称反应的催化剂，但是仍然需要相对低分子量的高效寡肽催化剂。在本文中，我们展示了形成β-发夹的四肽4的构象工程，该构象是Miller小组首次报道的，它是反式-2-（N-乙酰氨基）环己-1-醇（不饱和）的不对称酰基转移反应的催化剂（ķ相对= 28）。通过我们的主链修饰策略，将硫代酰胺和磺酰胺作为酰胺的等排物引入了β-发夹二级结构中。thioxo肽还采用β-发夹结构作为氧肽，并结合使用NMR，IR和X射线技术来支持。硫氧四肽14形成了更受约束的β-发夹构象，因此在同一反应中提供了更高的对映选择性（k rel = 109）。此外，四肽的构象变化的检查8在所述的质子化Ñ π -methylhistidine部分提供了证据来解释在不对称酰基转移反应的催化效率的变化。
• The reaction of phosphorus pentachloride with amides, in particular 2-acetamido-2-deoxyaldohexopyranoses
  作者：Anthony M. Dempsey、Leslie Hough

  DOI：10.1016/s0008-6215(00)87007-x

  日期：1975.5

  exopyranose polyacetates are transformed by the action of phosphorus pentachloride into 2-tetrachloroethylideneamino derivatives, the trans -2-acetamido-l-acetate system reacting more rapidly than the cis . A 1-acetamido-pyranosyl polyacetate afforded the 1-tetrachloroethylideneamino derivative and 2- O -trichloroacetyl-β- D -glucopyranosyl chloride. The latter was also observed, amongst other products

  摘要通过五氯化磷的作用，将2-乙酰氨基-2-脱氧醛二氢吡喃葡萄糖多乙酸酯转化为2-四氯亚乙基氨基衍生物，反式-2-乙酰氨基-1-乙酸体系的反应比顺式更快。1-乙酰氨基-吡喃葡萄糖基多乙酸酯提供了1-四氯亚乙基氨基衍生物和2-O-三氯乙酰基-β-D-吡喃葡萄糖基氯。除其他产物外，还观察到后者，是由β-D-吡喃葡萄糖基叠氮化物四乙酸酯与五氯化磷的反应引起的。在乙酰胺基环己烷及其2-乙酰氧基衍生物上进行的类似反应得到二氯乙酰胺基，三氯乙酰胺基和四氯乙叉基氨基衍生物。同样，1-乙酰氨基-2-乙酰氧基乙烷得到1-二氯乙酰氨基衍生物。
• Outer-Sphere Control for Divergent Multicatalysis with Common Catalytic Moieties
  作者：Christopher R. Shugrue、Bianca R. Sculimbrene、Elizabeth R. Jarvo、Brandon Q. Mercado、Scott J. Miller

  DOI：10.1021/acs.joc.8b03068

  日期：2019.2.1

  We herein report two examples of one-pot, simultaneous reactions, mediated by multiple, orthogonal catalysts with the same catalytic motif. First, BINOL-derived chiral phosphoric acids (CPA) and phosphothreonine (pThr)-embedded peptides were found to be matched for two different steps in double reductions of bisquinolines. Next, two pi-methylhistidine (Pmh)-containing peptides catalyzed enantio-and chemoselective acylations and phosphorylations of multiple substrates in one pot. The selectivity exhibited by common reactive moieties is adjusted solely by the appended chiral scaffold through outer-sphere interactions.
• Stereochemistry of Cyclic Amino-alcohols. Inversion, Retention and Participation
  作者：G. E. McCasland、R. K. Clark、Herbert E. Carter

  DOI：10.1021/ja01170a070

  日期：1949.2
• Raiford; Mortensen, Journal of the American Chemical Society, 1928, vol. 50, p. 1203
  作者：Raiford、Mortensen

  DOI：——

  日期：——