5,5-dimethyl-2-(2-nitrobenzylidene)cyclohexane-1,3-dione | 166036-30-2

• 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: 5,5-dimethyl-2-(2-nitrobenzylidene)cyclohexane-1,3-dione
• 英文别名: 5,5-Dimethyl-2-[(2-nitrophenyl)methylidene]cyclohexane-1,3-dione
• CAS: 166036-30-2
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: CCMDBJOMNDEWHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-2-(2-nitrobenzylidene)cyclohexane-1,3-dione 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 以61 %的产率得到3,3-dimethyl-3,4-dihydroacridin-1(2H)-one
  参考文献：
  名称：

  硼化镍促进还原环化合成喹啉和喹啉-2(1H)-酮衍生物

  摘要：

  公开了一种温和且有效的合成不同取代的喹啉和喹啉-2-酮衍生物的方法。原位生成的硼化镍被证明是还原环化反应的有效促进剂。广泛的底物范围、温和的反应条件、稳定的产率和广泛的官能团耐受性是新发现的反应的其他显着特征。采用这种分子内还原环化方案，可以制备毫克至多克规模的大量喹啉和喹啉-2-酮衍生物。

  DOI：

  10.1055/a-2116-5206
• 作为产物：
  描述：

  {2-[(2-hydroxy-4,4-dimethyl-6-oxo-cyclohex-1-enyl)-(2-nitro-phenyl)-methylsulfanyl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester 以 氘代氯仿 为溶剂， 生成 5,5-dimethyl-2-(2-nitrobenzylidene)cyclohexane-1,3-dione
  参考文献：
  名称：

  A Three-Component Photoreversible Tag for Thiols

  摘要：

  A one-pot coupling of a 1,3-diketone, an aldehyde, and an alkanethiol has been developed to produce a protected sulfide. Through use of an o-nitrophenylbenzaldehyde, this method provides a one-step route to a photochemically reversible thiol-protecting group. The kinetics of photolysis were established using H-1 NMR analysis, which allows for the rate to be based on the entire reaction scheme.

  DOI：

  10.1021/jo0481396

文献信息

• Ahluwalia; Sahay, Ranjana; Das, Umashankar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 11, p. 1211 - 1213
  作者：Ahluwalia、Sahay, Ranjana、Das, Umashankar

  DOI：——

  日期：——
• Synthesis of 3,4-dihydro-3,3-dimethyl-1(2H)-acridinone
  作者：Roberto Martínez、Georgina Espinosa-Pérez、Marco Brito-Arias

  DOI：10.1007/bf01666107

  日期：1995.4

  The acridinone derivative 3,4-dihydro-3,3-dimethyl-1(2H)-acridinone (4) has been prepared in a two step fashion and the molecular structure confirmed by X-ray diffraction. Compound 4 crystallizes in the space group P2(1)/n with a = 6.022(2), b = 21.111(2), c = 9.604(2) Angstrom, beta = 99.97(2)degrees, and Z = 4. The single crystal analysis showed the acridinone tricyclic ring is virtually planar except in the gem-dimethyl position of C(3) which presented a half-chair conformation.
• A Three-Component Photoreversible Tag for Thiols
  作者：Kristine M. Clarke、James J. La Clair、Michael D. Burkart

  DOI：10.1021/jo0481396

  日期：2005.4.1

  A one-pot coupling of a 1,3-diketone, an aldehyde, and an alkanethiol has been developed to produce a protected sulfide. Through use of an o-nitrophenylbenzaldehyde, this method provides a one-step route to a photochemically reversible thiol-protecting group. The kinetics of photolysis were established using H-1 NMR analysis, which allows for the rate to be based on the entire reaction scheme.
• Synthesis of Quinoline and Quinolin-2(1H)-one Derivatives via Nickel Boride Promoted Reductive Cyclization
  作者：Mrinal K. Bera、Rumpa Sarkar、Surya Kanta Samanta、Anila M. Menon、Deepak Chopra、Debabani Ganguly

  DOI：10.1055/a-2116-5206

  日期：2023.10

  diversely substituted quinoline and quinolin-2-one derivatives is disclosed. In situ generated nickel boride proved to be an effective promoter of the reductive cyclization reaction. Broad substrate scope, mild reaction conditions, consistent yield, and a wide range of functional group tolerance are the other notable features of the newly discovered reaction. A large number of quinoline and quinolin-2-one

  公开了一种温和且有效的合成不同取代的喹啉和喹啉-2-酮衍生物的方法。原位生成的硼化镍被证明是还原环化反应的有效促进剂。广泛的底物范围、温和的反应条件、稳定的产率和广泛的官能团耐受性是新发现的反应的其他显着特征。采用这种分子内还原环化方案，可以制备毫克至多克规模的大量喹啉和喹啉-2-酮衍生物。