trans-4-methyl-1-cyclohexyl pivalate | 838835-60-2

• 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-4-methyl-1-cyclohexyl pivalate
• CAS: 838835-60-2
• 化学式: C₁₂H₂₂O₂
• 分子量: 198.305
• InChiKey: ABFBPPBWGWOOIH-MGCOHNPYSA-N

物化性质

• 沸点：
  222.2±8.0 °C(Predicted)
• 密度：
  0.93±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  trans-4-methyl-1-cyclohexyl pivalate 在 dipotassium hydrogenphosphate 、 C₁₇H₁₈ClFeN₆O₆^(2-) 、 间氯过氧苯甲酸 作用下， 以 水 、 乙腈 为溶剂， 以85%的产率得到4-hydroxy-4-methylcyclohexyl pivalate
  参考文献：
  名称：

  铁配合物催化广泛的底物范围的选择性C–H键氧化

  摘要：

  据报道，在缩二脲修饰的TAML大环配体骨架（Fe–bTAML）的基础上，模仿过氧化物酶的Fe络合物可作为催化剂，对未活化的3°C–H键和活化的2°C– H键在接近中性的条件下和较低的底物范围（18种底物，包括芳烃，杂芳族化合物和极性官能团）下，具有低催化剂负载量（1 mol％）和高产物收率（优异的质量平衡）的H键。使用控制位点选择性的空间，电子和立体电子规则，可预测的选择性实现了复杂底物3°和2°位点的脂族C–H氧化，包括将（+）-青蒿素氧化为（+）-10β-羟基青蒿素。机理研究表明，Fe V（O）是这些反应过程中的活性氧化剂。

  DOI：

  10.1021/acs.orglett.6b03359

文献信息

• An Iron Catalyst for Oxidation of Alkyl CH Bonds Showing Enhanced Selectivity for Methylenic Sites
  作者：Irene Prat、Laura Gómez、Mercè Canta、Xavi Ribas、Miquel Costas

  DOI：10.1002/chem.201203281

  日期：2013.2.4

  Many are called but few are chosen: A nonheme iron complex catalyzes the oxidation of alkyl CH bonds by using H2O2 as the oxidant, showing an enhanced selectivity for secondary over tertiary CH bonds (see scheme).

  许多被称为但被选择几个：阿非血红素铁络合物催化烷基C的氧化 H键通过使用H 2 ö 2作为氧化剂时，示出了用于增强的选择性二次过叔C  H键（参见方案）。
• 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。
• Readily Accessible Bulky Iron Catalysts exhibiting Site Selectivity in the Oxidation of Steroidal Substrates
  作者：David Font、Mercè Canta、Michela Milan、Olaf Cussó、Xavi Ribas、Robertus J. M. Klein Gebbink、Miquel Costas

  DOI：10.1002/anie.201600785

  日期：2016.5.4

  Bulky iron complexes are described that catalyze the site‐selective oxidation of alkyl C−H bonds with hydrogen peroxide under mild conditions. Steric bulk at the iron center is introduced by appending trialkylsilyl groups at the meta‐position of the pyridines in tetradentate aminopyridine ligands, and this effect translates into high product yields, an enhanced preferential oxidation of secondary over

  描述了大铁络合物在温和条件下用过氧化氢催化烷基CH键的位点选择性氧化。通过在三齿氨基吡啶配体中吡啶的间位连接三烷基甲硅烷基，可以在铁中心引入大分子的立体化，这种作用转化为高产物产量，增强了仲碳氢键与仲碳氢键的优先氧化作用，并具有更高的分离能力。对萜类化合物和甾体基质中的亚甲基位点进行位点选择性氧化。甾族底物中C6和C12亚甲基位的空位选择性氧化显示出受催化剂手性支配。
• SUBSTITUTED IMIDAZOLES
  申请人：CHUBB NATHAN ANTHONY LOGAN

  公开号：US20080125473A1

  公开（公告）日：2008-05-29

  This invention relates to a range of alpha substituted 2-benzyl substituted imidazole compounds and pharmaceutically acceptable salts and solvates thereof, to compositions comprising such compounds, processes for their synthesis and their use as parasiticides.

  本发明涉及一系列α取代的2-苯甲基取代咪唑化合物及其药学上可接受的盐和溶剂化物，包括含有这种化合物的组合物，它们的合成过程以及它们作为寄生虫药物的用途。
• 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).