(-)(R)-3-methyl-1-phenyl-pentane | 69428-32-6

• 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: (-)(R)-3-methyl-1-phenyl-pentane
• 英文别名: (-)(R)-3-Methyl-1-phenyl-pentan；((S)-3-Methyl-pentyl)-benzol；[(3R)-3-methylpentyl]benzene
• CAS: 69428-32-6
• 化学式: C₁₂H₁₈
• 分子量: 162.275
• InChiKey: PVXCNEZDIJHZQB-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (-)(R)-3-methyl-1-phenyl-pentane 在 溶剂黄146 、 铂 作用下， 生成 (-)(R)-3-methyl-1-cyclohexyl-pentane
  参考文献：
  名称：

  Levene; Marker, Journal of Biological Chemistry, 1935, vol. 110, p. 311,319

  摘要：

  DOI：
• 作为产物：
  描述：

  (3S)-3-methyl-5-phenyl-1-pentyne 在 palladium on carbon 、 氢气 作用下， 生成 (-)(R)-3-methyl-1-phenyl-pentane
  参考文献：
  名称：

  SN2-Selective allylic substitution of chiral γ-aryl substituted allylic picolinates with alkynylcopper reagents

  摘要：

  Substitution of gamma-aryl secondary allylic picolinates with alkynyl copper reagents was studied. The copper reagent, prepared from TMSC equivalent to CMgBr and CuBr center dot Me-25 in 2:1, was subjected to substitution of the picolinate derived from (E)-3-phenyl-1-methyl-2-propenyl alcohol at 0 degrees C for 1 h in THF to produce a mixture of alpha- and gamma-products and the alcohol in 67:20:13, while the reagent in 3 or 4:1 ratio gave the alpha-product with 90-91% selectivity. On the contrary, reaction in CH2Cl2-THF (6-8:1) at 0 degrees C for 1 h furnished the alpha-product with 99% regioselectivity. The effect of CH2Cl2 was also demonstrated with eight more examples. Furthermore, 99% inversion was determined by transformation to the literature compound and by chiral H PLC. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.051

文献信息

• 10.1021/jacs.4c03610
  作者：Cao, Min、Wang, Hongliang、Hou, Fangao、Zhu, Yuhang、Liu, Qianqian、Tung, Chen-Ho、Liu, Lei

  DOI：10.1021/jacs.4c03610

  日期：——

  report a practical manganese-catalyzed enantio-differentiating hydroxylation of tertiary propargylic C–H bonds in acyclic systems, producing a wide range of structurally diverse enantioenriched tertiary propargyl alcohols in high efficiency with extremely efficient chemo- and enantio-discrimination. Other features include the use of C–H substrates as the limiting reagent, noteworthy functional group compatibility

  C(sp 3 )–H 键的直接位点选择性和对映选择性氧官能化形成具有一般范围、具有可预测选择性和制备有用产率的醇，代表了合成有机化学标准逻辑的范式转变。然而，对于用于对映体富集的叔醇合成的叔C-H键的酶促或非酶促不对称羟基化的了解非常缺乏。在这里，我们报道了无环体系中叔炔丙C-H键的实用锰催化对映差异化羟基化，以极其有效的化学和对映歧视的方式高效地产生了各种结构多样的对映体丰富的叔丙炔醇。其他特点包括使用 C-H 底物作为限制试剂、值得注意的官能团兼容性、出色的合成实用性和可扩展性。这些发现为开发具有挑战性的底物的金属催化不对称氧化提供了蓝图。
• Klages; Sautter, Chemische Berichte, 1904, vol. 37, p. 654
  作者：Klages、Sautter

  DOI：——

  日期：——
• Levene; Harris, Journal of Biological Chemistry, 1935, vol. 111, p. 725,728
  作者：Levene、Harris

  DOI：——

  日期：——
• Chardin, Chemisches Zentralblatt, 1908, vol. 79, # II, p. 1861
  作者：Chardin

  DOI：——

  日期：——
• SN2-Selective allylic substitution of chiral γ-aryl substituted allylic picolinates with alkynylcopper reagents
  作者：Qian Wang、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2010.08.051

  日期：2010.10

  Substitution of gamma-aryl secondary allylic picolinates with alkynyl copper reagents was studied. The copper reagent, prepared from TMSC equivalent to CMgBr and CuBr center dot Me-25 in 2:1, was subjected to substitution of the picolinate derived from (E)-3-phenyl-1-methyl-2-propenyl alcohol at 0 degrees C for 1 h in THF to produce a mixture of alpha- and gamma-products and the alcohol in 67:20:13, while the reagent in 3 or 4:1 ratio gave the alpha-product with 90-91% selectivity. On the contrary, reaction in CH2Cl2-THF (6-8:1) at 0 degrees C for 1 h furnished the alpha-product with 99% regioselectivity. The effect of CH2Cl2 was also demonstrated with eight more examples. Furthermore, 99% inversion was determined by transformation to the literature compound and by chiral H PLC. (C) 2010 Elsevier Ltd. All rights reserved.