(1RS,8aRS)-1-hydroxyindolizidine | 14174-78-8

• 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: (1RS,8aRS)-1-hydroxyindolizidine
• 英文别名: cis-1-hydroxyindolizidine；cis-1-hydtoxyindolizidine；(1R,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizin-1-ol
• CAS: 14174-78-8；14174-99-3；20312-32-7；70841-79-1；70841-80-4；108866-40-6；108866-41-7；112709-92-9；112709-93-0
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: IATZHJGSCGLJSL-HTQZYQBOSA-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：

  (1RS,8aRS)-1-hydroxyindolizidine 、 (+)-2,3-dibenzoyl-D-tartaric acid 生成 (2R,3R)-3-[[(8aR)-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：

  trans-N-benzyl-4-hydroxy-5-(iodomethyl)pyrrolidin-2-one 在 palladium dihydroxide 劳森试剂 、 咪唑 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三丁基氯化锡 、 氢气 、 triethyloxonium fluoroborate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 81.0h， 生成 (1RS,8aRS)-1-hydroxyindolizidine
  参考文献：
  名称：

  Electrophilic olefin heterocyclization in organic synthesis. Stereoselective synthesis of 4,5-disubstituted .gamma.-lactams by iodine-induced lactam formation of .gamma.,.delta.-unsaturated thioimidates

  摘要：

  DOI：

  10.1021/jo00281a022

文献信息

• 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。
• Tkahata, Hiroki; Tajima, Mayumi; Banba, Yasunori, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 9, p. 2550 - 2552
  作者：Tkahata, Hiroki、Tajima, Mayumi、Banba, Yasunori、Momose, Takefumi

  DOI：——

  日期：——
• Alkenyl and Aryl BoronatesMild Nucleophiles for the Stereoselective Formation of Functionalized <i>N</i>-Heterocycles
  作者：Robert A. Batey、D. Bruce MacKay、V. Santhakumar

  DOI：10.1021/ja983801z

  日期：1999.6.1
• Regio- and Stereoselective Functionalization of an Optically Active Tetrahydroindolizine Derivative. Catalytic Asymmetric Syntheses of Lentiginosine, 1,2-Diepilentiginosine, and Gephyrotoxin 209D
  作者：Seiji Nukui、Mikiko Sodeoka、Hiroaki Sasai、Masakatsu Shibasaki

  DOI：10.1021/jo00107a019

  日期：1995.1

  To demonstrate the usefulness of optically active 3,5,8,8a-tetrahydro-5-oxoindolizine (9) which is prepared by the catalytic asymmetric Heck-type cyclization, regio- and stereoselective functionalizations of(S)- and (R)-9 have been examined. Stereoselective epoxidation of 3,5,6,7,8,8a-hexahydro-5-oxoindolizine (10) obtained by the regioselective reduction was examined, and it was found that electrophile (peracid or bromonium cation) reacted from the opposite side of C-8a-H in a highly stereoselective manner. The catalytic asymmetric syntheses of lentiginosine (3) and 1,2-diepilentiginosine (4) using these stereoselective epoxidations have been achieved. Dihydroxylation of(S)-9 catalyzed by OsO4 gave (6R,7R,8aS)-3,5,6,7,8,8a-hexahydro-6,7-d (16) regio- and stereoselectively. Several other functionalizations and a synthesis of gephyrotoxin 209D (6) are also described. The origin of the high stereoselectivity observed in the functionalization of 9 is discussed based on the stereoelectronic principle such as the Cieplak model.
• TAKAHATA, HIROKI;TAKAMATSU, TAMOTSU;YAMAZAKI, TAKAO, J. ORG. CHEM., 54,(1989) N0, C. 4812-4822
  作者：TAKAHATA, HIROKI、TAKAMATSU, TAMOTSU、YAMAZAKI, TAKAO

  DOI：——

  日期：——