(1S,8aS)-1-Hydroxyindolizidine | 108866-40-6

• 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: (1S,8aS)-1-Hydroxyindolizidine
• 英文别名: (1S, 8AS)-Octahydroindolizin-1-OL；(1S,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizin-1-ol
• CAS: 108866-40-6
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: IATZHJGSCGLJSL-YUMQZZPRSA-N

物化性质

• 沸点：
  227.9±23.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,8aS)-1-Hydroxyindolizidine 、 (+)-2,3-dibenzoyl-D-tartaric acid 生成 (2R,3R)-3-[[(1S,8aS)-1,2,3,5,6,7,8,8a-octahydroindolizin-1-yl]oxycarbonyl]-2-benzoyl-2,3-dihydroxy-4-oxo-4-phenylbutanoic acid
  参考文献：
  名称：

  HARRIS, C. M.;HARRIS, T. M., TETRAHEDRON LETT., 28,(1987) N 23, 2559-2562

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,8aS)-1-Hydroxy-hexahydro-indolizin-5-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(1S,8aS)-1-Hydroxyindolizidine
  参考文献：
  名称：

  1-羟基吲哚并咪唑类化合物（有毒吲哚并立生物碱slaframine和swainsonine的生物合成前体）的不对称合成

  摘要：

  描述了通过遵循Sharpless动力学拆分，分子内酰胺化和自由基Michael加成等关键步骤，由外消旋N-苄氧基羰基-3-羟基-4-戊烯基胺（3）对映选择性合成1-羟基吲哚嗪（1和2）的方法。

  DOI：

  10.1016/s0957-4166(00)80439-5

文献信息

• Amino acids as precursors to indolizidine alkaloids
  作者：Mukund P. Sibi、James W. Christensen

  DOI：10.1016/s0040-4039(00)97933-4

  日期：1990.1

  Enantiocontrolled synthesis of indolizidine alkaloids δ-coniceine [(−)-(R)-octahydroindolizine] and (+)-(1S, 8aS)-1-hydroxyindolizidine, the biosynthetic precursor of slaframine, have been achieved through a condensation of L-prolinal and 3R,2S-hydroxyprolinal, respectively, with a 3-carbon synthon.

  吲哚并立生物碱δ-可卡因[（-）-（R）-八氢吲哚并嗪和slaframine的生物合成前体（+）-（1S，8aS）-1-羟基吲哚并嗪]的对映体控制合成通过L-脯氨酸的缩合反应实现和3R，2S-羟基脯氨醛，分别带有3-碳合成子。
• Stereochemistry of remote dianion addition to imines. Application to the synthesis of (1S, 8aS)-1-hydroxyindolizidine
  作者：Diana L.C. Green、James J. Kiddle、Charles M. Thompson

  DOI：10.1016/0040-4020(95)00037-9

  日期：1995.3

  A stereoselective route to (1S, 8aS)-1-hydroxyindolizidine is reported herein that incorporates as a pivotal step the diastereoselective addition of the dianion of 4-(phenylsulfonyl)butanoic acid (4-PSBA) to a chiral α-benzyloxymethyl imine.

  （1立体选择性路线小号，8α小号）-1- hydroxyindolizidine在本文报道了包含作为关键步骤的非对映选择性加入4-（苯磺酰基）丁酸（4-PSBA）的二价阴离子的手性α -苄氧基甲基亚胺。
• Synthesis and configurational assignment of optically active 1-hydroxyindolizidines
  作者：Constance M. Harris、Thomas M. Harris

  DOI：10.1016/s0040-4039(00)96147-1

  日期：1987.1

  The four diastereomers of 1-hydroxyindolizidine have been prepared in high optical purity (>98%) by NaBH4 reduction of the (+) and (-) 3-bromocamphor-8-sulfonic acid salts of 1-oxoindolizidine followed by separation of the resulting diastereomeric alcohols by ion-exchange chromatography.

  通过NaBH 4还原1-氧代吲哚并啶的（+）和（-）3-溴樟脑8-磺酸盐，然后分离N通过离子交换色谱法得到非对映体醇。
• The synthesis of (1S,8aS)-1-hydroxyindolizidine using a stereoselective Grignard addition to an N-benzyl-3-deoxy sugar imine derived from D-Glucose
  作者：Y. Jagadeesh、B. Chandrasekhar、B. Venkateswara Rao

  DOI：10.1016/j.tetasy.2010.08.001

  日期：2010.9

  A highly stereoselective approach to 1-hydroxyindolizidine is described using a Grignard reaction on N-benzyl imine derived from 3-deoxy-1,2-O-isopropylidine-alpha-D-xylo-pentodialdofuranose and reductive cyclization as key steps. (C) 2010 Elsevier Ltd. All rights reserved.
• Enantiospecific Synthesis of (−)-Slaframine and Related Hydroxylated Indolizidines. Utilization of a Nucleophilic Alaninol Synthon Derived from Serine¹
  作者：Mukund P. Sibi、James W. Christensen

  DOI：10.1021/jo9908546

  日期：1999.8.1

  A general methodology for the synthesis of indolizidine alkaloids delta-coniceine (12), 1-hydroxyindolizidine (20), desacetoxy slaframine (24), slaframine (34), and an analogue (37) has been developed. This convergent approach utilizes the available chirality in proline and serine and is conceptually different from other approaches. A highly stereoselective coupling of the prolinals with a nucleophilic alaninol synthon provides the precursors for the key cyclization. A novel thermolytic annulation of an oxazolidinone is the key step in the formation of the six-membered piperidine ring. Further elaboration provides the target natural products 24, 34, and 37 in good overall yields.