(+)-neomenthyl pivalate | 1421312-58-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+)-neomenthyl pivalate
• 英文别名: (+)-neomethyl pivalate；[(1S,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2,2-dimethylpropanoate
• CAS: 1421312-58-4
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: NUAKVDBHRFXQNU-AGIUHOORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-neomenthyl pivalate 在 [Fe(CF₃SO₃)₂((S,S)-N,N’-bis(2-pyridylmethyl)-2,2’-bipyrrolidine)] 、 双氧水 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 生成 [(1S,2R,5R)-2-(2-hydroxypropan-2-yl)-5-methylcyclohexyl] 2,2-dimethylpropanoate 、 [(1S,2S,5S)-5-methyl-4-oxo-2-propan-2-ylcyclohexyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  易于接触的大铁催化剂在甾类底物的氧化中表现出位选择性

  摘要：

  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。

  DOI：

  10.1002/anie.201600785
• 作为产物：
  描述：

  (1Alpha,2Alpha,5β)-(+-)-5-甲基 、 三甲基乙酰氯 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 以75%的产率得到(+)-neomenthyl pivalate
  参考文献：
  名称：

  Regioselective Oxidation of Nonactivated Alkyl C–H Groups Using Highly Structured Non-Heme Iron Catalysts

  摘要：

  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).

  DOI：

  10.1021/jo302196q

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）。
• Kinase Inhibitors And Their Uses
  申请人：Ding Pingyu

  公开号：US20070142402A1

  公开（公告）日：2007-06-21

  The present disclosure provides compounds that inhibit protein kinases, such as JAK, Axl, or Syk kinases, compositions comprising the compounds and methods of using the compounds to inhibit protein kinase and treat and/or prevent diseases associated with inappropriate kinase activity.

  本公开提供了抑制蛋白激酶的化合物，例如JAK、Axl或Syk激酶，包括该化合物的组合物以及使用该化合物抑制蛋白激酶并治疗和/或预防与不适当激酶活性相关的疾病的方法。
• Cycloalkyl Substituted Pyrimidinediamine Compounds And Their Uses
  申请人：Li Hui

  公开号：US20070299060A1

  公开（公告）日：2007-12-27

  The present disclosure provides 2,4-pyrimidinediamine compounds having antiproliferative activity, compositions comprising the compounds and methods of using the compounds to inhibit cellular proliferation and to treat proliferate diseases such as tumorigenic cancers.

  本公开提供具有抗增殖活性的2,4-嘧啶二胺化合物，包含该化合物的组合物以及使用该化合物抑制细胞增殖和治疗增殖性疾病，如肿瘤性癌症的方法。
• US7601713B2
  申请人：——

  公开号：US7601713B2

  公开（公告）日：2009-10-13
• US7754714B2
  申请人：——

  公开号：US7754714B2

  公开（公告）日：2010-07-13