cis-Decalon-(1) | 936-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-Decalon-(1)
• 英文别名: (4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-2H-naphthalen-1-one
• CAS: 936-17-4
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: AFEFRXAPJRCTOW-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-Decalon-(1) 生成 (+)-trans-1-decalone
  参考文献：
  名称：

  GRAS J.-L.; BERTRAND M., TETRAHEDRON LETT., 1979, NO 47, 4549-4552

  摘要：

  DOI：
• 作为产物：
  描述：

  (4aS,8aR)-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one 生成 cis-Decalon-(1)
  参考文献：
  名称：

  GRAS J.-L.; BERTRAND M., TETRAHEDRON LETT., 1979, NO 47, 4549-4552

  摘要：

  DOI：

文献信息

• The Iron(II) Complex [Fe(CF₃SO₃)₂(mcp)] as a Convenient, Readily Available Catalyst for the Selective Oxidation of Methylenic Sites in Alkanes
  作者：Mercè Canta、David Font、Laura Gómez、Xavi Ribas、Miquel Costas

  DOI：10.1002/adsc.201300923

  日期：2014.3.10

  The efficient and selective oxidation of secondary CH sites of alkanes is achieved by using low catalyst loadings of a non‐expensive, readily available iron catalyst [Fe(II)(CF3SO3)2(mcp)], Fe‐mcp, [mcp=N,N′‐dimethyl‐N,N′‐bis(2‐pyridylmethyl)cyclohexane‐trans‐1,2‐diamine]}, and hydrogen peroxide (H2O2) as oxidant, via a simple reaction protocol. Natural products are selectively oxidized and isolated

  次级C的有效和选择性氧化烷烃h的位点是通过使用非昂贵的，容易得到的铁催化剂的低催化剂负载的[Fe（II）（CF实现3 SO 3）2（MCP）]， Fe的MCP，[MCP = ñ，N'-二甲基- ñ，N' -双（2-吡啶基甲基）环己烷TRAN S--1,2-二胺]}，和过氧化氢（H 2 ö 2）作为氧化剂，通过一个简单的反应方案。天然产物被选择性地氧化并以合成上可接受的产率分离。容易获得大量催化剂和CH氧化过程的简便性使得该系统成为在制备规模上以较短的反应时间进行烷烃CH氧化反应的特别方便的工具。
• Regioselective Oxidation of Nonactivated Alkyl C–H Groups Using Highly Structured Non-Heme Iron Catalysts
  作者：Laura Gómez、Mercè Canta、David Font、Irene Prat、Xavi Ribas、Miquel Costas

  DOI：10.1021/jo302196q

  日期：2013.2.15

  Selective oxidation of alkyl C-H groups constitutes one of the highest challenges in organic synthesis. In this work, we show that mononuclear iron coordination complexes Lambda-[Fe(CF3SO3)(2)((S,S,R)-MCPP)] (Lambda-1P), Delta-[Fe(CF3SO3)(2)((R,R,R)-MCPP)] (Delta-1P), Lambda-[Fe(CF3SO3)(2)((S,S,R)-BPBPP)] (Lambda-2P), and Delta-[Fe(CF3SO3)(2)((R,R,R)-BPBPP)] (Delta-2P) catalyze the fast, efficient, and selective oxidation of nonactivated alkyl C-H groups employing H2O2 as terminal oxidant. These complexes are based on tetradentate N-based ligands and contain iron centers embedded in highly structured coordination sites defined by two bulky 4,5-pinenopyridine donor ligands, a chiral diamine ligand backbone, and chirality at the metal (Lambda or Delta). X-ray diffraction analysis shows that in Lambda-1P and Lambda-2P the pinene rings create cavity-like structures that isolate the iron site. The efficiency and regioselectivity in catalytic C-H oxidation reactions of these structurally rich complexes has been compared with those of Lambda-[Fe(CF3SO3)(2)((S,S)-MCP)] (Lambda-1), Lambda-[Fe(CF3SO3)(2)((S,S)-BPBP)] (Lambda-2), Delta-[Fe(CF3SO3)(2)((R,R)-BPBP)] (Delta-2), Lambda-[Fe(CH3CN)(2)((S,S)-BPBP)] (SbF6)(2) (Lambda-2SbF(6)), and Delta-[Fe(CH3CN)(2)((R,R)-BPBP)](SbF6)(2) (Delta-2SbF(6)), which lack the steric bulk introduced by the pinene rings. Cavity-containing complexes Lambda-1P and Lambda-2P exhibit enhanced activity in comparison with Delta-1P, Delta-2P, Lambda-1, Lambda-2, and Lambda-2SbF(6). The regioselectivity exhibited by catalysts Lambda-1P, Lambda-2P, Delta-1P, and Delta-2P in the C-H oxidation of simple organic molecules can be predicted on the basis of the innate properties of the distinct C-H groups of the substrate. However, in specific complex organic molecules where oxidation of multiple C-H sites is competitive, the highly elaborate structure of the catalysts allows modulation of C-H regioselectivity between the oxidation of tertiary and secondary C-H groups and also among multiple methylene sites, providing oxidation products in synthetically valuable yields. These selectivities complement those accomplished with structurally simpler oxidants, including non-heme iron catalysts Lambda-2 and Lambda-2SbF(6).
• MACDONALD T. L.; MAHALINGAM S., J. AMER. CHEM. SOC., 1980, 102, NO 6, 2113-2115
  作者：MACDONALD T. L.、 MAHALINGAM S.

  DOI：——

  日期：——
• KOENIG, THOMAS M.;DAEUBLE, JOHN F.;BRESTENSKY, DONNA M.;STRYKER, JEFFREY +, TETRAHEDRON LETT., 31,(1990) N3, C. 3237-3240
  作者：KOENIG, THOMAS M.、DAEUBLE, JOHN F.、BRESTENSKY, DONNA M.、STRYKER, JEFFREY +

  DOI：——

  日期：——
• BRIFFAUD, T.;LARPENT, C.;PATIN, H., J. CHEM. SOC. CHEM. COMMUN. ,(1990) N7, C. 1193-1194
  作者：BRIFFAUD, T.、LARPENT, C.、PATIN, H.

  DOI：——

  日期：——