(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-diazo-3-phenylpropanoate | 158393-62-5

• 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: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-diazo-3-phenylpropanoate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-diazo-3-phenylpropanoate
• CAS: 158393-62-5
• 化学式: C₁₉H₂₆N₂O₂
• 分子量: 314.428
• InChiKey: PCSNZGCROWHBCI-UWWQBHOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-diazo-3-phenylpropanoate 在 过氧乙酸 、 dirhodium tetraacetate 、 mercury(II) diacetate 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 3-苯基丙烷-1,2-二醇
  参考文献：
  名称：

  使用α-硅酸酯的不对称烷基化和将不对称金属卡宾插入SiH键中来制备旋光性α-甲硅烷基羰基化合物

  摘要：

  已经通过三种不同的途径以高收率和合理的非对映选择性制备了取代的α-甲硅烷基酯。前两个涉及母体α-甲硅烷基酯烯酸酯的烷基化，其中手性助剂存在于硅或酯官能团上。使用泛内酯作为手性助剂，发现第三种途径涉及将金属类金属化合物不对称地插入SiH键中，从而提供更好的非对映选择性。

  DOI：

  10.1016/s0040-4020(97)00002-1
• 作为产物：
  描述：

  L-薄荷醇 在 sodium acetate 、 sodium hydride 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 反应 96.0h， 生成 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 2-diazo-3-phenylpropanoate
  参考文献：
  名称：

  Asymmetric metal carbene insertion into the SiH bond

  摘要：

  alpha-Silyl-alpha-substituted acetic esters have been prepared in good yields and reasonable diastereoselectivities using an asymmetric metal carbene insertion into the Si-H bond. Optically active 1,2-diols were then prepared after reduction of the ester and conversion of the C-Si bond into a C-OH bond.

  DOI：

  10.1016/s0040-4039(00)60729-3

文献信息

• A Boron Scan of Ethyl Acetoacetate Leads to Versatile Building Blocks
  作者：Alina Trofimova、Brandon White、Diego B. Diaz、Martynas J. Širvinskas、Alan Lough、Travis Dudding、Andrei K. Yudin

  DOI：10.1002/anie.202319842

  日期：2024.4.8

  Discovered in the 19th century, ethyl acetoacetate has been central to the development of organic chemistry. This study presents borylated derivatives of this venerable molecule. We show how the corresponding building blocks can be converted into borylated heterocycles. The regiochemistry of homologation of acyl-MIDA (N-methyliminodiacetic acid) boronates with diazoacetates was found to be related to the

  乙酰乙酸乙酯于 19 世纪被发现，一直是有机化学发展的核心。这项研究提出了这种古老分子的硼化衍生物。我们展示了如何将相应的结构单元转化为硼化杂环。发现酰基-MIDA（ N-甲基亚氨基二乙酸）硼酸酯与重氮乙酸酯同系物的区域化学与重氮物质的空间体积有关。
• Convenient Synthetic Route to an Enantiomerically Pure FMOC α-Amino Acid
  作者：Douglass F. Taber、James F. Berry、Timothy J. Martin

  DOI：10.1021/jo801781v

  日期：2008.12.5

  A strategy for the facile alpha-amination of carboxylic acid menthyl esters is described. The resulting diastereomers, readily separable, can be individually carried on to each enantiomer of the FMOC alpha-amino acid. A variety of unnatural side chains were compatible with this approach. The menthyl ester was easily removed from the FMOC alpha-amino acid without racermization.
• Preparation of optically active α-silylcarbonyl compounds using asymmetric alkylation of α-silylacetic esters and asymmetric metal-carbene insertion into the SiH bond
  作者：Yannick Landais、Denis Planchenault

  DOI：10.1016/s0040-4020(97)00002-1

  日期：1997.2

  Substituted α-silylacetic esters have been prepared in good yields and with reasonable diastereoselectivities by three different routes. The first two involved alkylation of the parent α-silylacetic ester enolates, with the chiral auxiliaries being present either on silicon or on the ester function. The third route involving asymmetric insertion of metal-carbenoids into the SiH bond was found to afford

  已经通过三种不同的途径以高收率和合理的非对映选择性制备了取代的α-甲硅烷基酯。前两个涉及母体α-甲硅烷基酯烯酸酯的烷基化，其中手性助剂存在于硅或酯官能团上。使用泛内酯作为手性助剂，发现第三种途径涉及将金属类金属化合物不对称地插入SiH键中，从而提供更好的非对映选择性。
• Asymmetric metal carbene insertion into the SiH bond
  作者：Yannick Landais、Denis Planchenault

  DOI：10.1016/s0040-4039(00)60729-3

  日期：1994.6

  alpha-Silyl-alpha-substituted acetic esters have been prepared in good yields and reasonable diastereoselectivities using an asymmetric metal carbene insertion into the Si-H bond. Optically active 1,2-diols were then prepared after reduction of the ester and conversion of the C-Si bond into a C-OH bond.