(8aS)-8,8A-二氢-3H-吲嗪-5-酮 | 151983-41-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: (8aS)-8,8A-二氢-3H-吲嗪-5-酮
• 英文名称: (S)-3,5,8,8a-tetrahydro-5-oxo-indolizine
• 英文别名: (8As)-8,8a-dihydro-3H-indolizin-5-one
• CAS: 151983-41-4
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: ZQMVMMOCVVDNOC-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (8aS)-8,8A-二氢-3H-吲嗪-5-酮 在 platinum(IV) oxide lithium aluminium tetrahydride 、 氢气 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 生成 (+)-coniceine
  参考文献：
  名称：

  催化不对称合成功能化的吲哚并咪唑衍生物。适用于合成各种糖苷酶抑制剂的有用中间体

  摘要：

  通过前手性烯基碘5开始，通过不对称的Heack反应（Pd（O）-BPPFOH，Ag交换的沸石），吲哚唑烷衍生物7的合成度高达86％ee 。还描述了将7转化为δ-可卡因（9）。

  DOI：

  10.1016/s0040-4039(00)74058-5
• 作为产物：
  描述：

  (S)-1-(2-allyl-2H-pyrrol-1(5H)-yl)prop-2-en-1-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 生成 (8aS)-8,8A-二氢-3H-吲嗪-5-酮
  参考文献：
  名称：

  Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles

  摘要：

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.

  DOI：

  10.1021/ol900880w

文献信息

• Asymmetric heck reaction of alkenyl iodides in the presence of silver salts. Catalytic asymmetric synthesis of decalin and functionalized indolizidine derivatives
  作者：Yoshihiro Sato、Seiji Nukui、Mikiko Sodeoka、Masakatsu Shibasaki

  DOI：10.1016/s0040-4020(01)80761-4

  日期：1994.1

  Decalin derivatives 3 (up to 80% ee) and indolizidine derivative 6 (up to 86% ee) have been synthesized by an asymmetric Heck reaction starting with prochiral alkenyl iodides 1 and 4, respectively. The important role of silver salts in the asymmetric Heck reaction is discussed, and the conversion of 6 to δ-coniceine (24) is also described.

  通过不对称的Heck反应，分别从前手性烯基碘化物1和4开始，合成了十氢化萘衍生物3（至多80％ee）和吲哚并咪唑衍生物6（至多86％ee）。讨论了银盐在不对称Heck反应中的重要作用，还描述了6到δ-可卡因的转化（24）。
• Asymmetric Synthesis of Unsaturated Monocyclic and Bicyclic Nitrogen Heterocycles
  作者：Hiroshi Nomura、Christopher J. Richards

  DOI：10.1021/ol900880w

  日期：2009.7.2

  Hydrolysis of scalemic trichloroacetamides Cl3CCONHCH(R)CHCH2 and allylation, or acylation with but-3-enoic acid, followed by ring-closing metathesis resulted in the formation of unsaturated pyrrolidine and piperidine building blocks. These were employed in the synthesis of (S)-coniine (R = Pr) and a formal synthesis of (+)-anisomycin (R = p-MeOC5H4). Extension of this methodology with R = CH2CHCH2 employing two ring-closing metatheses resulted in the synthesis of unsaturated quinolizidinone and indolizidinone frameworks.
• Catalytic asymmetric synthesis of a functionalized indolizidine derivative. A useful intermediate suitable for the synthesis of various glycosidase inhibitors
  作者：Seiji Nukui、Mikiko Sodeoka、Masakatsu Shibasaki

  DOI：10.1016/s0040-4039(00)74058-5

  日期：1993.7

  Indolizidine derivative 7 has been sythesized in up 86% ee by an asymmetric Heack reaction (Pd(O)-BPPFOH, Ag-exchanged zeolite) starting with prochiral alkenyl iodide 5. Conversion of 7 to δ-coniceine (9) is also described.

  通过前手性烯基碘5开始，通过不对称的Heack反应（Pd（O）-BPPFOH，Ag交换的沸石），吲哚唑烷衍生物7的合成度高达86％ee 。还描述了将7转化为δ-可卡因（9）。