1,5-diphenylpentane-1,3-diol | 61952-19-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1,5-diphenylpentane-1,3-diol
• 英文别名: rac-(1R,3S)-1,5-diphenylpentane-1,3-diol；(+)-threo-1,5-diphenylpentane-1,3-diol；(1R,3S)-1,5-diphenylpentane-1,3-diol；threo-1,5-diphenylpentane-1,3-diol
• CAS: 61952-19-0
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: XOCHIQZDEBSMIX-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,5-diphenylpentane-1,3-diol 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Regioselective Ring Opening of Di-isopropylsilylenes Derived from 1,3-Diols with Alkyl Lithium Reagents

  摘要：

  The selective alkyl lithium-induced ring opening of 1,3-di-isopropylsilylenes is described. The reaction affords a differentially substituted 1,3-diol bearing a silane that resides at the oxygen in the more sterically demanding position. The reaction can be highly selective with a regiochemical preference up to >50:1 and likely proceeds via an alkoxy-silane intermediate. This intermediate can by trapped by methyl iodide to provide the corresponding silyl methyl ether, wherein the silane again resides at the oxygen in the more sterically demanding position.

  DOI：

  10.1021/acs.orglett.5b02529
• 作为产物：
  描述：

  DL-扁桃酸甲酯 在 盐酸 、 氢气 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1,5-diphenylpentane-1,3-diol
  参考文献：
  名称：

  Heteroatom directed β-lithiation of a vinyl ether

  摘要：

  DOI：

  10.1016/s0040-4039(01)81737-8

文献信息

• Double Catalytic Kinetic Resolution (DoCKR) of Acyclic <i>anti</i> -1,3-Diols: The Additive Horeau Amplification
  作者：Jérémy Merad、Prashant Borkar、Frédéric Caijo、Jean-Marc Pons、Jean-Luc Parrain、Olivier Chuzel、Cyril Bressy

  DOI：10.1002/anie.201709844

  日期：2017.12.11

  two successive enantioselective organocatalytic acylation reactions, and leads to diesters and recovered diols with high enantiopurities. It was first developed with C2‐symmetrical diols and then further extended to non‐C2‐symmetrical anti diols to prepare useful chiral building blocks. The protocol is highly practical as it only requires 1 mol % of a commercially available organocatalyst and leads

  本文所述的协同双催化动力学拆分（DoCKR）概念已成功应用于外消旋无环抗-1,3-二醇（天然产物中的常见基序）。该方法利用了涉及两个连续的对映选择性有机催化酰化反应的加性Horeau扩增的优势，并产生了具有高对映纯度的二酯和回收的二醇。它首先用C 2对称二醇开发，然后进一步扩展到非C 2对称抗氧化剂。二醇来制备有用的手性结构单元。该方案是高度实用的，因为它仅需要1 mol％的市售有机催化剂，并导致易于分离的产物。该程序用于报告的最短的全合成（+）-隐脂内酯，这是一种具有抗发芽活性的天然产物。
• Stereoselective catalytic tishchenko reduction of β-hydroxyketones using scandium triflate
  作者：Kevin M. Gillespie、Ian J. Munslow、Peter Scott

  DOI：10.1016/s0040-4039(99)01986-3

  日期：1999.12

  A number of aliphatic and aromatic beta-hydroxyketones were reduced to 1,3-diol monoesters by aldehydes in the presence of a catalytic amount of scandium triflate. Chiral substrates were reduced with high 1,3-anti diastereoselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Regioselective Ring Opening of Di-isopropylsilylenes Derived from 1,3-Diols with Alkyl Lithium Reagents
  作者：Katelyn M. Chando、Patricia A. Bailey、Joseph A. Abramite、Tarek Sammakia

  DOI：10.1021/acs.orglett.5b02529

  日期：2015.11.6

  The selective alkyl lithium-induced ring opening of 1,3-di-isopropylsilylenes is described. The reaction affords a differentially substituted 1,3-diol bearing a silane that resides at the oxygen in the more sterically demanding position. The reaction can be highly selective with a regiochemical preference up to >50:1 and likely proceeds via an alkoxy-silane intermediate. This intermediate can by trapped by methyl iodide to provide the corresponding silyl methyl ether, wherein the silane again resides at the oxygen in the more sterically demanding position.
• Heteroatom directed β-lithiation of a vinyl ether
  作者：Patrick G. McDougal、Joseph G. Rico

  DOI：10.1016/s0040-4039(01)81737-8

  日期：1984.1