trans-2-(N-phenylcarbonylamino)-1-cyclohexanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: trans-2-(N-phenylcarbonylamino)-1-cyclohexanol
• 英文别名: N-[(1S,2S)-2-hydroxycyclohexyl]benzamide
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: WIJPGRLOJGSUFK-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2-(N-phenylcarbonylamino)-1-cyclohexanol 在 氯化亚砜 、 1,2-二氯乙烷 作用下， 生成 cis-3a,4,5,6,7,7a-hexahydro-2-phenylbenzoxazole
  参考文献：
  名称：

  Ring Closure of the 2-Benzoylaminocyclohexanols. The Mechanism of Oxazoline Formation

  摘要：

  DOI：

  10.1021/ja01161a088
• 作为产物：
  描述：

  (1S,2S)-反式-1,3-氨基环己醇盐酸盐 在 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 trans-2-(N-phenylcarbonylamino)-1-cyclohexanol
  参考文献：
  名称：

  Application of new chiral auxiliaries, trans-2-(N-arylsulfonyl-N-benzyl)cyclohexanols, in an asymmetric radical cyclization

  摘要：

  New chiral auxiliaries, truans-2-(N-arylsulfonyl-N-benzyl)cyclohexanols were prepared and applied to an asymmetric radical cyclization. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00340-2

文献信息

• Chemistry and Biology of Diazonamide A:  Second Total Synthesis and Biological Investigations
  作者：K. C. Nicolaou、Junliang Hao、Mali V. Reddy、Paraselli Bheema Rao、Gerasimos Rassias、Scott A. Snyder、Xianhai Huang、David Y.-K. Chen、William E. Brenzovich、Nicolas Giuseppone、Paraskevi Giannakakou、Aurora O'Brate

  DOI：10.1021/ja040093a

  日期：2004.10.1

  As an especially unique target for chemical synthesis, diazonamide A has the potential to be constructed through a plethora of synthetic routes, each attended by different challenges and opportunities for discovery. In this article, we detail our second total synthesis of diazonamide A through a sequence entirely distinct from that employed in our first campaign, one whose success required the development

  作为化学合成的一个特别独特的目标，重氮酰胺 A 有可能通过多种合成路线构建，每一条都面临着不同的挑战和发现机会。在本文中，我们详细介绍了第二次重氮酰胺 A 的全合成，其序列与我们第一次战役中使用的序列完全不同，该战役的成功需要开发几种特殊的战略和战术。我们还公开了我们关于重氮酰胺 A 及其结构同系物的化学生物学的完整研究，并更全面地描述了我们使用吡啶缓冲 POCl(3) 进行 Robinson-Gabriel 环脱水的方案的范围。
• Highly stereoselective chlorination of β-substituted cyclic alcohols using PPh3–NCS: factors that control the stereoselectivity
  作者：E. A. Jaseer、Ajay B. Naidu、Sreehari S. Kumar、R. Koteshwar Rao、Krishna G. Thakur、G. Sekar

  DOI：10.1039/b614512d

  日期：——

  A variety of trans-β-substituted cyclic alcohols were stereoselectively chlorinated to either the corresponding cis-chloride or trans-chloride (inversion or retention of configuration) with good to excellent yields; the stereochemical outcome is determined by the size of the ring and the nature of the β-substituents, especially the electronegativity of the substituted atom.

  多种反式-β-取代环醇被立体选择性地氯化，获得相应的顺式氯化物或反式氯化物（构型翻转或保留），产率良好至优秀；立体化学结果取决于环的大小和β-取代基的性质，特别是取代原子的电负性。
• Thermal rearrangement of xanthates to dithiolcarbonates—I
  作者：Tanezo Taguchi、Michiko Nakao

  DOI：10.1016/s0040-4020(01)92658-4

  日期：——

  S-methyl xanthates, dl-trans-2-dimethylaminocyclohexyl S-methyl xanthalate was rearranged without elimination to the corresponding dithiolcarbonate while the cis isomer suffered over-all elimination. It has been suggested that the dimethylamino group attached to the carbon carrying the xanthate group induces the rearrangement. Other examples studied support this mechanism. 2-Benzamidoethyl S-methyl and

  在β-二烷基氨基烷基S-甲基黄原酸酯的热解过程中，顺式异构体被全部消除，而dl-反式-2-二甲基氨基环己基S-甲基黄酸酯被重排而不被消除成相应的二硫代碳酸酯。已经提出，连接至带有黄原酸酯基团的碳的二甲基氨基基团引起重排。研究的其他示例也支持这种机制。2-苄酰胺基乙基S-甲基和dl-反式-2-苯甲酰胺基环己基S-甲基黄原酸酯已被转化为相应的恶唑啉衍生物。
• Catalytic Alkene Difunctionalization via Imidate Radicals
  作者：Kohki M. Nakafuku、Stacy C. Fosu、David A. Nagib

  DOI：10.1021/jacs.8b07578

  日期：2018.9.12

  The first catalytic strategy to harness imidate radicals has been developed. This approach enables alkene difunctionalization of allyl alcohols by photocatalytic reduction of their oxime imidates. The ensuing imidate radicals undergo consecutive intra- and intermolecular reactions to afford (i) hydroamination, (ii) aminoalkylation, or (iii) aminoarylation, via three distinct radical mechanisms. The

  第一个利用酰亚胺自由基的催化策略已经开发出来。这种方法可以通过光催化还原烯丙醇的肟酰亚胺酯来实现烯丙醇的烯烃双官能化。随后的亚氨酸酯自由基经历连续的分子内和分子间反应，通过三种不同的自由基机制提供(i)氢胺化、(ii)氨基烷基化或(iii)氨基芳基化。介绍了这种亚胺酯自由基反应催化方法的广泛范围和实用性，以及与其他 N 中心自由基和互补的闭壳亚胺酯途径的比较。
• Nitrogen-containing cyclohetero cycloalkylaminoaryl derivatives for CNS
  申请人：G. D. Searle & Co.

  公开号：US05130330A1

  公开（公告）日：1992-07-14

  Certain nitrogen-containing cyclohetero cycloalkylaminoaryl compounds are described for treatment of CNS disorders such as cerebral ischemia, psychotic disorders and convulsions. Compounds of particular interest are of the formula ##STR1## wherein R.sup.1 is selected from hydrido, loweralkyl, cycloalkylalkyl of four to six carbon atoms, and loweralkenylloweralkyl; wherein each of R.sup.2 and R.sup.3 is independently selected from hydrido and loweralkyl; wherein each of R.sup.4 through R.sup.7, R.sup.10 and R.sup.11 is independently selected from hydrido, hydroxy, loweralkyl, benzyl, phenoxy, benzyloxy and haloloweralkyl; wherein n is a number selected from four through six; wherein p is a number selected from zero through four; wherein q is a number selected from three through five; wherein A is selected from phenyl, naphthyl and thienyl; wherein any of the foregoing A groups can be further substituted with one or more substituents independently selected from hydrido, hydroxy, loweralkyl, loweralkoxy, halo, haloloweralkyl, amino, monoloweralkylamino and diloweralkylamino; or a pharmaceutically acceptable salt thereof.

  描述了用于治疗中枢神经系统疾病如脑缺血、精神疾病和癫痫的某些含氮环杂环烷基氨基芳基化合物。特别感兴趣的化合物的结构如下：其中R.sup.1从氢、较低烷基、四至六个碳原子的环烷基烷基和较低烯基较低烷基中选择；其中R.sup.2和R.sup.3各自独立地选择自氢和较低烷基；其中R.sup.4到R.sup.7、R.sup.10和R.sup.11各自独立地选择自氢、羟基、较低烷基、苄基、苯氧基、苄氧基和卤代较低烷基；其中n是从四到六选择的数字；其中p是从零到四选择的数字；其中q是从三到五选择的数字；其中A从苯基、萘基和噻吩基中选择；其中上述任何A基可以进一步用一个或多个取代基独立选择自氢、羟基、较低烷基、较低烷氧基、卤、卤代较低烷基、氨基、单烷基氨基和双烷基氨基进行取代；或其药学上可接受的盐。