(S)-3-benzyloxyoctanal | 64250-49-3

• 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: (S)-3-benzyloxyoctanal
• 英文别名: 3(S)-Benzyloxy-1-octanal；(3S)-3-phenylmethoxyoctanal
• CAS: 64250-49-3
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: QJOARTKNLBRXKV-HNNXBMFYSA-N

物化性质

• 沸点：
  337.8±17.0 °C(Predicted)
• 密度：
  0.968±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (S)-carbonyl(cyclopentadienyl)octanoyl(triphenylphosphino)iron 、 (S)-3-benzyloxyoctanal 在 正丁基锂 、 氯化二乙基铝 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以130 mg的产率得到(3S,4S,2'S)-3-hexyl-4-(2'-benzyloxyhept-1'-yl)oxetan-2-one
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydrolipstatin and valilactone

  摘要：

  The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(eta(5)-C5H5)Fe(CO)(PPh3)] and beta-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to beta-substituted and alpha,beta-disubstituted beta-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetra hydrolipstatin and valilactone. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.012
• 作为产物：
  描述：

  dipentylzinc 在 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) titanium(IV) isopropylate 作用下， 反应 0.17h， 生成 (S)-3-benzyloxyoctanal
  参考文献：
  名称：

  A new catalytic asymmetric approach to polyfunctional aldol products mediated by zinc organometallics

  摘要：

  The catalytic asymmetric addition of functionalized dialkylzincs to beta-alkoxyaldehydes provides after a short sequence of functional group interconversions aldol products in 40-99% ee. Their stereoselective transformation to either syn- or anti-1,3-diols has been performed.

  DOI：

  10.1016/s0040-4039(00)73804-4

文献信息

• Novel analogs of prostaglandins with 4-oxo-thiazolidinyl nucleus and
  申请人：Merck & Co., Inc.

  公开号：US04022794A1

  公开（公告）日：1977-05-10

  This invention relates to novel 9-thia-, 9-oxothia-, and 9-dioxothia-11-oxo-12-azaprostanoic acid compounds, salts, and derivatives thereof and also to processes for the preparation of such compounds. These compounds have prostaglandin-like biological activity and are particularly useful as renal vasodilators, as platelet aggregation inhibitors, and for the treatment of certain autoimmune diseases.

  本发明涉及新型9-硫代、9-氧代硫代和9-二氧代硫代-11-氧代-12-氮杂前列腺酸化合物、盐及其衍生物，以及制备这样的化合物的方法。这些化合物具有类似前列腺素的生物活性，特别适用于作为肾脏血管扩张剂、血小板聚集抑制剂以及治疗某些自身免疫性疾病。
• US4022794A
  申请人：——

  公开号：US4022794A

  公开（公告）日：1977-05-10
• A new catalytic asymmetric approach to polyfunctional aldol products mediated by zinc organometallics
  作者：Paul Knochel、Walter Brieden、Michael J. Rozema、Christina Eisenberg

  DOI：10.1016/s0040-4039(00)73804-4

  日期：1993.9

  The catalytic asymmetric addition of functionalized dialkylzincs to beta-alkoxyaldehydes provides after a short sequence of functional group interconversions aldol products in 40-99% ee. Their stereoselective transformation to either syn- or anti-1,3-diols has been performed.
• Asymmetric synthesis of tetrahydrolipstatin and valilactone
  作者：Stephen C. Case-Green、Stephen G. Davies、Paul M. Roberts、Angela J. Russell、James E. Thomson

  DOI：10.1016/j.tetasy.2008.11.012

  日期：2008.11

  The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(eta(5)-C5H5)Fe(CO)(PPh3)] and beta-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to beta-substituted and alpha,beta-disubstituted beta-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetra hydrolipstatin and valilactone. (C) 2008 Elsevier Ltd. All rights reserved.