(3R,4S)-3-hydroxy-4-(1-propenyl)-2-octanone | 95331-64-9

• 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: (3R,4S)-3-hydroxy-4-(1-propenyl)-2-octanone
• 英文别名: (3R,4S)-3-hydroxy-4-[(E)-prop-1-enyl]octan-2-one
• CAS: 95331-64-9
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: AKNGTPHSQKETIM-HQVCXTMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-hydroxy-4-(1-propenyl)-2-octanone 在 zinc(II) tetrahydroborate 、 苦味酸 作用下， 以 乙醚 为溶剂， 反应 20.33h， 生成 (2S,3R,4S)-2,3-isopropylidene-dioxy-4-(1-propenyl)octane
  参考文献：
  名称：

  （+）-blastmycinone的立体选择性合成

  摘要：

  （+）-Blastmycinone是基于（2R，3S）-2-羟基-3-（1-丙烯基）庚酸通过（R）-（E）-1-甲基的烯醇酯Claisen重排的非对映选择性合成而合成的-2-庚烯基乙醇酸酯和Zn（BH 4）2立体选择性还原α-羟基酮。

  DOI：

  10.1016/s0040-4039(01)81550-1
• 作为产物：
  描述：

  (S)-3-octyn-2-ol 在 Lindlar's catalyst 、 四丁基碘化铵 、 mercury(II) sulfate sodium hydroxide 、 正丁基锂 、 硫酸 、 乙基溴化镁 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (3R,4S)-3-hydroxy-4-(1-propenyl)-2-octanone
  参考文献：
  名称：

  不对称 [2,3] WITTIG 重排在三个连续手性中心的立体控制中的应用。(+)-BLASTMYCINONE 的新合成

  摘要：

  描述了一种新的 (+)-blastmycinone 合成方法，它依赖于不对称 [2,3] Wittig 重排与用硼氢化锌选择性还原 α-羟基酮的组合。

  DOI：

  10.1246/cl.1985.1723

文献信息

• Methods
  申请人：Sattentau James Quentin

  公开号：US20070110759A1

  公开（公告）日：2007-05-17

  The presence of aldehydic groups on proteins and lipoproteins is associated with various pathological conditions such as atherosclerosis, diabetes and alcoholic liver disease. Respiratory syncytial virus (RSV) is a major cause of severe respiratory disease in infants and the elderly. RSV vaccine research has been impeded because a formalin-inactivated vaccine used in the 1960s predisposed infants to enhanced disease following subsequent natural infection. The molecular basis for the vaccine-induced hypersensitivity has not, however, been elucidated. We show here that addition of reactive carbonyl groups to ovalbumin (OVA) by treatment with glycolaldehyde or formaldehyde increases the protein's immunogenicity in mice, and biases the immune response towards a Th2-type response. The increased immunogenicity and the Th2-type response can both be abrogated by reductive elimination of the reactive carbonyl groups. We demonstrate that RSV inactivated by formaldehyde (FI-RSV), following a protocol used previously to prepare the vaccine, contains reactive carbonyl groups. Using a well-established model of FI-RSV vaccine-induced pathology, immunisation of mice with FI-RSV and subsequent challenge of the mice with live RSV induced Th2-type responses, lung eosinophilia and weight loss that were abrogated by reductive elimination of the reactive carbonyl groups. We thus propose that the addition of reactive carbonyl groups to RSV during inactivation is the major mechanism that drives the Th2-immune response and associated pathology. Moreover, we suggest that the addition of reactive carbonyl groups to other antigens, including vaccines, may be responsible for other hypersensitive and allergic reactions described in the literature.
• APPLICATION OF ASYMMETRIC [2,3]WITTIG REARRANGEMENT TO STEREOCONTROL OVER THREE CONTIGUOUS CHIRAL CENTERS. A NEW SYNTHESIS OF (+)-BLASTMYCINONE
  作者：Noboru Sayo、Ei-ichi Nakai、Takeshi Nakai

  DOI：10.1246/cl.1985.1723

  日期：1985.11.5

  A new synthesis of (+)-blastmycinone is described which relies on the combination of the asymmetric [2,3]Wittig rearrangement with the selective reduction of an α-hydroxy ketone with zinc borohydride.

  描述了一种新的 (+)-blastmycinone 合成方法，它依赖于不对称 [2,3] Wittig 重排与用硼氢化锌选择性还原 α-羟基酮的组合。
• Stereoselective synthesis of (+)-blastmycinone
  作者：Tamotsu Fujisawa、Hiromasa Kohama、Kazuhisa Tajima、Toshio Sato

  DOI：10.1016/s0040-4039(01)81550-1

  日期：1984.1

  (+)-Blastmycinone has been synthesized based on diastereoselective synthesis of (2R,3S)-2-hydroxy-3-(1-propenyl)heptanoic acid by the ester enolate Claisen rearrangement of (R)-(E)-1-methyl-2-heptenyl glycolate and stereoselective reduction of α-hydroxy ketone with Zn(BH4)2.

  （+）-Blastmycinone是基于（2R，3S）-2-羟基-3-（1-丙烯基）庚酸通过（R）-（E）-1-甲基的烯醇酯Claisen重排的非对映选择性合成而合成的-2-庚烯基乙醇酸酯和Zn（BH 4）2立体选择性还原α-羟基酮。