10,11-O-cyclohexylidene-12β-hydroxy-13β-(1-tetrahydro-β-carbolinyl)tetrahydrofuran | 171082-26-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: 10,11-O-cyclohexylidene-12β-hydroxy-13β-(1-tetrahydro-β-carbolinyl)tetrahydrofuran
• 英文别名: 1-(10,11-O-cydohexylidene-12β-hydroxy-13α-tetrahydro-furanyl)tetrahydro-β-carboline；(3aR,5R,6S,6aR)-5-[(1S)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]spiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]-6-ol
• CAS: 171082-26-1
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: QVUVNKFUOAPDOF-CENDIDJXSA-N

物化性质

• 沸点：
  620.2±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  75.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10,11-O-cyclohexylidene-12β-hydroxy-13β-(1-tetrahydro-β-carbolinyl)tetrahydrofuran 在 硫酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 80.0h， 生成 3-Benzyloxy-6,12-dihydro-7H-indolo[2,3-a]quinolizin-5-ylium; hydrogen sulfate
  参考文献：
  名称：

  Synthesis of Indolo[2,3-a]quinolizidine-3-One

  摘要：

  The title compound 1 has been synthesised through the intermediacy of the salt 5 obtained by acid hydrolysis of the optically active beta-carboline derivative 10, 11-cyclohexylidene-12 beta-hydroxy-13 beta-(1-tetrahydro-beta-carbolinyl)tetrahydrofuran (4).

  DOI：

  10.1080/00397919508011435
• 作为产物：
  描述：

  色胺 、 di-(1,2-O-cyclohexylidene-α-D-xylopentodialdofuranose-5-hydrate)-5,5':3',5-dianhydride 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以58%的产率得到10,11-O-cyclohexylidene-12β-hydroxy-13β-(1-tetrahydro-β-carbolinyl)tetrahydrofuran
  参考文献：
  名称：

  Synthesis of Indolo[2,3-a]quinolizidine-3-One

  摘要：

  The title compound 1 has been synthesised through the intermediacy of the salt 5 obtained by acid hydrolysis of the optically active beta-carboline derivative 10, 11-cyclohexylidene-12 beta-hydroxy-13 beta-(1-tetrahydro-beta-carbolinyl)tetrahydrofuran (4).

  DOI：

  10.1080/00397919508011435

文献信息

• Microwave Assisted Pictet–Spengler and Bischler–Napieralski Reactions
  作者：Bikash Pal、Parasuraman Jaisankar、Venkatachalam S. Giri

  DOI：10.1081/scc-120021516

  日期：2003.1.7

  Abstract Pictet–Spengler and Bischler–Napieralski reaction products have been prepared–using microwave irradiation on silicagel support under solvent free condition. Microwave assisted reactions have resulted in better yields of the desired products than prepared under conventional conditions.

  摘要 Pictet-Spengler 和 Bischler-Napieralski 反应产物已在无溶剂条件下在硅胶载体上使用微波辐射制备。微波辅助反应比在常规条件下制备的所需产物的产率更高。
• [EN] FLAVOPEREIRINE DERIVATIVES FOR CANCER THERAPY<br/>[FR] DERIVES DE FLAVOPEREIRINE POUR LE TRAITEMENT DU CANCER
  申请人：DABUR RES FOUNDATION

  公开号：WO2005121143A1

  公开（公告）日：2005-12-22

  The present invention relates to novel derivatives of flavopereirine and methods for manufacture thereof. The novel derivatives of flavopereirine are useful for inhibition or prevention of the growth or multiplication of cancer cells, and to therapeutic compositions containing such compounds. The invention more specifically relates to the use of derivatives of flavopereirine for the inhibition and / or prevention of cancer of the ovary, breast, prostate, pancreas, oral cavity, lung, colon, and larynx.

  本发明涉及新型的黄檗碱衍生物及其制备方法。这些新型的黄檗碱衍生物对抑制或预防癌细胞的生长或增殖具有用处，并且用于含有这些化合物的治疗组合物。该发明更具体地涉及利用黄檗碱衍生物来抑制和/或预防卵巢、乳腺、前列腺、胰腺、口腔、肺、结肠和喉癌。
• An Unusual Diastereoselective Pictet–Spengler Reaction: Synthesis of Novel Tetrahydro-β-Carboline Glycosides
  作者：Prasun Pradhan、Debkumar Nandi、Soma Pradhan、Parasuraman Jaisankar、V. Giri

  DOI：10.1055/s-0032-1317632

  日期：——

  An unusual kinetic approach to the Pictet–Spengler reaction was investigated, in which l - or d -tryptophan methyl ester ­reacted with aldehydes of 1,2- O -cyclohexylidene-3-allyloxy-α- d -xylofuranose, yielding exclusively the cis or trans diastereomer of tetrahydro-β-carboline glycoside, respectively, with complete ­stereocontrol.

  研究了 Pictet-Spengler 反应的一种不寻常的动力学方法，其中 l-或 d-色氨酸甲酯与 1,2-O-环己叉-3-烯丙氧基-α-d-木呋喃糖的醛反应，仅产生顺式或分别具有完全立体控制的四氢-β-咔啉糖苷的反式非对映异构体。
• Synthesis of Indolo[2,3-<i>a</i>]quinolizidine-3-One
  作者：Ranjan K. Manna、Parasuraman Jaisankar、Venkatachalam S. Giri

  DOI：10.1080/00397919508011435

  日期：1995.10

  The title compound 1 has been synthesised through the intermediacy of the salt 5 obtained by acid hydrolysis of the optically active beta-carboline derivative 10, 11-cyclohexylidene-12 beta-hydroxy-13 beta-(1-tetrahydro-beta-carbolinyl)tetrahydrofuran (4).