N-cyclohexyl-1-oxo-2,3-dihydro-1H-indene-2-carboxamide | 1422194-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: N-cyclohexyl-1-oxo-2,3-dihydro-1H-indene-2-carboxamide
• CAS: 1422194-17-9
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: GTAOLLGYRBQFDL-UHFFFAOYSA-N

物化性质

• 沸点：
  486.8±35.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-1-oxo-2,3-dihydro-1H-indene-2-carboxamide 在 copper diacetate 、 N-氟代双苯磺酰胺 作用下， 生成
  参考文献：
  名称：

  Ar-BINMOL衍生的SalanCopper配合物催化β-酮酰胺的对映选择性氟化

  摘要：

  AbstractA facile and powerful enantioselective construction of CF containing molecules was successfully developed through asymmetric fluorination of β‐ketoamides catalyzed by Ar‐BINMOL‐derived salan–CuII system (Ar‐BINMOL=1,1′‐Binaphthalene‐2‐α‐arylmethanol‐2′‐ol, Cu = copper). The present catalytic system exhibited excellent enantioselectivity and a broad substrate scope for indanone‐derived β‐ketoamides under mild conditions (up to 99 % ee and 99 % yields). Notably, the biomimetic salan‐copper complex was demonstrated for the first time to be a highly efficient catalyst in the fluorination of β‐ketoamides. Experimental results and mechanistic studies indicated that both excess amount of copper salt and electrophilic attack of cationic fluorine to activated methylene assisted by amide group on the β‐ketoamides were key factors for high yield and excellent enantioselectivity, respectively, in this enantioselective fluorination, which was controlled by the two‐point binding between the salan–copper complex with cyclic β‐ketoamides and hydrogen‐bonding activation of the electrophilic fluorinating reagent.magnified image

  DOI：

  10.1002/adsc.201400603
• 作为产物：
  描述：

  1-茚酮 在 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 生成 N-cyclohexyl-1-oxo-2,3-dihydro-1H-indene-2-carboxamide
  参考文献：
  名称：

  在温和条件下用 TMSCF2Br 对 β-酮酰胺进行高选择性二氟甲基化

  摘要：

  在不使用任何过渡金属和其他添加剂的情况下，已开发出在温和条件下使用 TMSCF2Br 试剂选择性二氟甲基化 β-酮酰胺的有效方法。该协议允许以优异的产率（高达 93%）和高碳/氧 (C/O) 区域选择性（高达 99:1）方便地获取各种 α-二氟甲基 β-酮酰胺。β-酮酰胺的 C/O 选择性可以通过简单地改变碱来轻松逆转和控制。该协议可以很容易地扩大规模，并且可以将 C-二氟甲基化产物还原为含 CF2H 的氨基醇衍生物。此外，β-酮酰胺的第一个对映选择性亲电二氟甲基化已经通过相转移催化实现。

  DOI：

  10.1055/a-1507-5878

文献信息

• Magnesium Monoperphthalate (MMPP): a Convenient Oxidant for the Direct Rubottom Oxidation of Malonates, β‐Keto Esters, and Amides
  作者：Sara Meninno、Rosaria Villano、Alessandra Lattanzi

  DOI：10.1002/ejoc.202100098

  日期：2021.3.19

  Commercially available and inexpensive magnesium monoperphthalate (MMPP) was found to be an effective oxidant for the first direct Rubottom hydroxylation of α‐substituted malonates, β‐ketoesters, and β‐ketoamides, when working in ethanol at room temperature and using NaHCO3 as basic additive. The feasibility of gram scale oxidation was also demonstrated.

  当在室温下在乙醇中工作并且使用NaHCO 3作为碱性溶液时，发现市售廉价的单过苯甲酸镁（MMPP）是α-取代的丙二酸酯，β-酮酸酯和β-酮酰胺的首次直接Rubottom羟基化的有效氧化剂。添加剂。还证明了克级氧化的可行性。
• Asymmetric α-Hydroxylation of β-Indanone Esters and β-Indanone Amides Catalyzed by C-2′ Substituted <i>Cinchona</i> Alkaloid Derivatives
  作者：Yakun Wang、Hang Yin、Hai Qing、Jingnan Zhao、Yufeng Wu、Qingwei Meng

  DOI：10.1002/adsc.201500911

  日期：2016.3.3

  asymmetric α‐hydroxylation of β‐indanone esters and β‐indanone amides using peroxide as the oxidant was realized with a new C‐2′ substituted Cinchona alkaloid derivatives. The two enantiomers of α‐hydroxy‐β‐indanone esters could be obtained by simply changing the oxidant. This protocol allows a convenient access to the corresponding α‐hydroxy‐β‐indanone esters and α‐hydroxy‐β‐indanone amides with up to

  通过使用新的C-2'取代的金鸡纳生物碱衍生物，实现了使用过氧化物作为氧化剂的β-茚满酮酯和β-茚满酮酰胺的高度催化不对称α-羟基化反应。只需改变氧化剂即可获得α-羟基-β-茚满酮酯的两种对映体。该方案可方便地获得相应的α-羟基-β-茚满酮酯和α-羟基-β-茚满酮酰胺，产率高达99％，ee高达98％。
• Visible light-mediated selective α-functionalization of 1,3-dicarbonyl compounds <i>via</i> disulfide induced aerobic oxidation
  作者：Jingnan Zhao、Fan Yang、Zongyi Yu、Xiaofei Tang、Yufeng Wu、Cunfei Ma、Qingwei Meng

  DOI：10.1039/c9cc06544j

  日期：——

  A visible light-mediated α-functionalization of 1,3-dicarbonyl compounds with switchable selectivity induced by disulfide is disclosed. Upon irradiation with visible light, the metal- and base-free α-hydroxylation or α-hydroxymethylation reaction proceeded smoothly through a disulfide-catalyzed oxidation under mild conditions. The combination of a continuous-flow strategy could further improve the

  公开了可见光介导的1，3-二羰基化合物的α-官能化，其具有由二硫化物诱导的可选择性切换。在可见光照射下，无金属和无碱的α-羟基化或α-羟甲基化反应在温和的条件下通过二硫键催化的氧化反应顺利进行。连续流策略的组合可以进一步提高反应效率。
• Enantioselective α-hydroxylation of β-ketoamides
  作者：Claudia De Fusco、Sara Meninno、Consiglia Tedesco、Alessandra Lattanzi

  DOI：10.1039/c2ob27283k

  日期：——

  The first enantioselective α-hydroxylation reaction of α-substituted β-ketoamides has been developed by using the commercially available hydroquinine/TBHP system. The tertiary alcohols are obtained in good to high yield and up to 83% ee, which can be improved by a single crystallization.

  通过使用可商购的产品开发了第一个α-取代的β-酮酰胺的对映选择性α-羟基化反应 对苯二酚/ TBHP系统。可以以高至高收率和高达83％ee的价格获得叔醇，这可以通过单次结晶来改进。
• High-efficiency α-benzoyloxylation and hydroxylation of β-keto amides by phase transfer catalysis
  作者：Yakun Wang、Qinghe Gao、Nan Li、Yifan Chen、Jingwen Cui、Feiyu Gao、Qingwei Meng

  DOI：10.1016/j.tet.2018.06.026

  日期：2018.7

  A facile and efficient protocol for α-benzoyloxylation and α-hydroxylation of β-keto amides by phase-transfer catalysis is presented. This methodology provides mild and practical access to a variety ofα-oxygenated β-keto amides. Furthermore, α-benzoyloxylation products can be easily converted into α-hydroxylation compounds, which are useful synthetic precursors of biological targets.

  提出了一种通过相转移催化α-苯甲酰氧基化和β-酮酰胺的α-羟基化的简便有效方案。这种方法为各种α-氧化的β-酮酰胺提供了温和而实用的途径。此外，α-苯甲酰氧基化产物可以容易地转化成α-羟基化化合物，其是有用的生物靶标的合成前体。