6-Benzyloxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-non-3-yn-5-one | 89497-46-1

• 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: 6-Benzyloxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-non-3-yn-5-one
• 英文别名: 8-Methyl-1-(oxan-2-yloxy)-6-phenylmethoxynon-3-yn-5-one
• CAS: 89497-46-1
• 化学式: C₂₂H₃₀O₄
• 分子量: 358.478
• InChiKey: HGDFFOOYRCFVAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Benzyloxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-non-3-yn-5-one 在 喹啉 、 Pd-BaSO₄ 、 zinc(II) tetrahydroborate 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  立体选择性合成类固醇侧链和CD环。通往（±）-de-ab-cholesta-8（14），22-dien-9-one的途径

  摘要：

  立体选择性合成（±）-de-AB-cholesta-8（14），22-dien-9-（±）-赤藓基-6-苄氧基-5-羟基-8-甲基-1-四氢吡喃基氧基-3提出了通过两个克莱森重排的（Z）-壬烯作为维生素D 3的前体。

  DOI：

  10.1016/s0040-4039(00)88931-5
• 作为产物：
  描述：

  2-(3-丁炔氧基)四水-2H-吡喃 、 (+/-)-2-benzyloxy-N,N,4-trimethyl-pentanamide 以60%的产率得到6-Benzyloxy-8-methyl-1-(tetrahydro-pyran-2-yloxy)-non-3-yn-5-one
  参考文献：
  名称：

  立体选择性合成类固醇侧链和CD环。通往（±）-de-ab-cholesta-8（14），22-dien-9-one的途径

  摘要：

  立体选择性合成（±）-de-AB-cholesta-8（14），22-dien-9-（±）-赤藓基-6-苄氧基-5-羟基-8-甲基-1-四氢吡喃基氧基-3提出了通过两个克莱森重排的（Z）-壬烯作为维生素D 3的前体。

  DOI：

  10.1016/s0040-4039(00)88931-5

文献信息

• Stereoselective reduction of α-alkoxy acetylenic ketones with zinc borohydride and K-selectride.
  作者：Takashi Takahashi、Masahiro Miyazawa、Jiro Tsuji

  DOI：10.1016/s0040-4039(00)98885-3

  日期：1985.1

  Reduction of α-benzyloxy acetylenic ketones with zinc borohydride afforded the erythro-acetylenic vicinal diols in 95% stereoselectivity, while reduction with K-selectride gave the isomeric threo-diols in 90% stereoselectivity.

  用硼氢化锌还原α-苄氧基炔基酮可得到立体选择性为95％的赤-炔邻位二醇，而用K-selectride还原可得到90％立体选择性为异构的苏-二醇。
• TAKAHASHI, TAKASHI;MIYAZAWA, MASAHIRO;TSUJI, JIRO, TETRAHEDRON LETT., 1985, 26, N 42, 5139-5142
  作者：TAKAHASHI, TAKASHI、MIYAZAWA, MASAHIRO、TSUJI, JIRO

  DOI：——

  日期：——
• 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.