(1(S),2(R),8(S),8a(S))-8-Hydroxy-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone | 152185-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1(S),2(R),8(S),8a(S))-8-Hydroxy-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone
• 英文别名: (1S,2R,8S,8aS)-8-hydroxy-1,2-(iso-propylidenedioxy)octahydro-5-indolizidinone
• CAS: 152185-81-4
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: NGTBXJRLBRIVQS-WPYKOPORSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.13
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1(S),2(R),8(S),8a(S))-8-Hydroxy-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone 在 盐酸 、 dimethyl sulfide borane 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 (1S,2R,8R,8aS)-octahydro-1,2,8-indolizidinetriol
  参考文献：
  名称：

  An acylnitroso cycloaddition approach to the synthesis of highly oxygenated indolizidine alkaloids

  摘要：

  A synthetic approach to the synthesis of highly oxygenated indolizidine alkaloids is described. A key feature of the approach is intramolecular [4 + 2] cycloaddition between an acylnitroso dienophile and a tethered diene moiety, followed by ring contraction of the 1,2-oxazine so formed to a pyrrolidine. The requisite intermediates were prepared in optically pure form froM L-glutamic acid.

  DOI：

  10.1021/jo00074a040
• 作为产物：
  描述：

  (S)-(-)-4-<(tert-Butyldiphenylsilyl)oxy>-5(E),7-octadienohydroxamic acid 在 disodium hydrogenphosphate 、 四氧化锇 、 N-甲基吲哚酮 、 sodium amalgam 、 tetrapropylammonium periodate 、 Dowex H⁽¹⁺⁾ resin 、 四丁基氟化铵 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 51.0h， 生成 (1(S),2(R),8(S),8a(S))-8-Hydroxy-1,2-(isopropylidenedioxy)octahydro-5-indolizidinone
  参考文献：
  名称：

  An acylnitroso cycloaddition approach to the synthesis of highly oxygenated indolizidine alkaloids

  摘要：

  A synthetic approach to the synthesis of highly oxygenated indolizidine alkaloids is described. A key feature of the approach is intramolecular [4 + 2] cycloaddition between an acylnitroso dienophile and a tethered diene moiety, followed by ring contraction of the 1,2-oxazine so formed to a pyrrolidine. The requisite intermediates were prepared in optically pure form froM L-glutamic acid.

  DOI：

  10.1021/jo00074a040

文献信息

• A flexible enantioselective approach to 3,4-dihydroxyprolinol derivatives by SmI2-mediated reductive coupling of chiral nitrone with ketones/aldehydes
  作者：Hong-Kui Zhang、Shou-Qiang Xu、Jia-Jia Zhuang、Jian-Liang Ye、Pei-Qiang Huang

  DOI：10.1016/j.tet.2012.06.006

  日期：2012.8

  derivatives was described, which is based on the samarium diiodide-mediated reductive coupling of the chiral nitrone (3S,4R)-8, derived from d-isoascorbic acid with aldehydes/ketones. Thereby, polyhydroxyprolinol derivatives 9a–e and 9h–j were obtained from aromatic ketones and aliphatic aldehydes in good to excellent yields of 65–91%. These reductive hydroxyalkylations are highly diastereoselective

  描述了一种灵活的对映多羟基化脯氨醇衍生物的对映选择性方法，该方法基于io二碘化物介导的衍生自d-异抗坏血酸与醛/酮的手性硝酮（3 S，4 R）-8的还原偶联。因此，从芳族酮和脂族醛中获得多羟基脯氨醇衍生物9a – e和9h – j的产率高达65–91％。这些还原性羟烷基化在建立C-4立体异构中心时具有很高的非对映选择性。通过这种方式，（-）-8a- epi- swainsonine（4）和（-）-8,8a-di- Epi - swainsonine（5）已实现。
• An acylnitroso cycloaddition approach to the synthesis of highly oxygenated indolizidine alkaloids
  作者：Gary E. Keck、Duane R. Romer

  DOI：10.1021/jo00074a040

  日期：1993.10

  A synthetic approach to the synthesis of highly oxygenated indolizidine alkaloids is described. A key feature of the approach is intramolecular [4 + 2] cycloaddition between an acylnitroso dienophile and a tethered diene moiety, followed by ring contraction of the 1,2-oxazine so formed to a pyrrolidine. The requisite intermediates were prepared in optically pure form froM L-glutamic acid.