(E)-2,6-dimethyl-8-(oxan-2-yloxy)oct-2-enal | 817163-29-4

• 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: (E)-2,6-dimethyl-8-(oxan-2-yloxy)oct-2-enal
• CAS: 817163-29-4
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: QKRUGVBUADUJKT-VGOFMYFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2,6-dimethyl-8-(oxan-2-yloxy)oct-2-enal 在 sodium tetrahydroborate 、 碘 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(E)-2,6-Dimethyl-8-(tetrahydro-pyran-2-yloxy)-oct-2-en-1-ol
  参考文献：
  名称：

  Speedy and Regioselective 1,2-Reduction of Conjugated α,β-Unsaturated Aldehydes and Ketones Using NaBH₄/I₂

  摘要：

  Synthesis of allylic alcohols from alpha,beta-unsaturated aldehydes/ketones has been achieved in excellent yields utilizing NaBH4 and iodine. This reducing agent is mild and tolerant to a number of functional groups.

  DOI：

  10.1081/scc-120015699
• 作为产物：
  描述：

  6-chloro-3,7-dimethyl-7-octenol THP-ether 在 萘 、 sodium 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 20.5h， 生成 (E)-2,6-dimethyl-8-(oxan-2-yloxy)oct-2-enal
  参考文献：
  名称：

  Reactivity of TEMPO anion as a nucleophile and its applications for selective transformations of haloalkanes or acyl halides to aldehydes

  摘要：

  Sodium 2,2,6,6-tetramethylpiperidine-N-oxide (TEMPO-Na+), generated by reduction of TEMPO. with sodium naphthalenide in THF, reacted with alkyl halides or acyl halides to produce O-alkylated or acylated TEMPOs, which were in turn oxidized with mCPBA or reduced with DIBAL-H to afford the corresponding aldehydes, thus accomplishing a new protocol for the halides-carbonyls conversion. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.067

文献信息

• Efficient Role of Ionic Liquid (bmim)HSO₄ as Novel Catalyst for Monotetrahydropyranylation of Diols and Tetrahydropyranylation of Alcohols
  作者：Jasvinder Singh、Neeraj Gupta、Goverdhan L. Kad、Jasamrit Kaur

  DOI：10.1080/00397910600770839

  日期：2006.9.1
• Reactivity of TEMPO anion as a nucleophile and its applications for selective transformations of haloalkanes or acyl halides to aldehydes
  作者：Tsutomu Inokuchi、Hiroyuki Kawafuchi

  DOI：10.1016/j.tet.2004.09.067

  日期：2004.12

  Sodium 2,2,6,6-tetramethylpiperidine-N-oxide (TEMPO-Na+), generated by reduction of TEMPO. with sodium naphthalenide in THF, reacted with alkyl halides or acyl halides to produce O-alkylated or acylated TEMPOs, which were in turn oxidized with mCPBA or reduced with DIBAL-H to afford the corresponding aldehydes, thus accomplishing a new protocol for the halides-carbonyls conversion. (C) 2004 Elsevier Ltd. All rights reserved.
• Speedy and Regioselective 1,2-Reduction of Conjugated α,β-Unsaturated Aldehydes and Ketones Using NaBH₄/I₂
  作者：Jasvinder Singh、Irvinder Kaur、Jasamrit Kaur、Aman Bhalla、Goverdhan L. Kad

  DOI：10.1081/scc-120015699

  日期：2003.3

  Synthesis of allylic alcohols from alpha,beta-unsaturated aldehydes/ketones has been achieved in excellent yields utilizing NaBH4 and iodine. This reducing agent is mild and tolerant to a number of functional groups.