(10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione | 183904-54-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione
• 英文别名: (-)-12-Oxocalanolide B；(16S,17S)-10,10,16,17-tetramethyl-6-propyl-3,9,15-trioxatetracyclo[12.4.0.02,7.08,13]octadeca-1(14),2(7),5,8(13),11-pentaene-4,18-dione
• CAS: 183904-54-3
• 化学式: C₂₂H₂₄O₅
• 分子量: 368.43
• InChiKey: HQVBDUZROQMWRN-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione 在 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 cerium(III) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 12-Azidocalanolide B
  参考文献：
  名称：

  Structure−Activity Modifications of the HIV-1 Inhibitors (+)-Calanolide A and (−)-Calanolide B

  摘要：

  The Delta(7,8) olefinic linkages within (+)-calanolide A (1) and (-)-calanolide B (2) were catalytically reduced to determine impact on the anti-HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.

  DOI：

  10.1021/jm9602827
• 作为产物：
  描述：

  5-Hydroxy-6-((2R,3S)-3-hydroxy-2-methyl-butyryl)-2,2-dimethyl-10-propyl-2H-pyrano[2,3-f]chromen-8-one 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (10S,11S)-10,11-dihydro-4-propyl-6,6,10,11-tetramethyl-2H,6H,12H-benzo[1,2-b;3,4-b';5,6-b'']tripyran-2,12-dione
  参考文献：
  名称：

  Synthesis of (+)-calanolide A, an anti-HIV agent, Via enzyme-catalyzed resolution of the aldol products

  摘要：

  The synthesis of (+)-calanolide A (1), an anti-HIV-1 agent, is described. A TiCl4-mediated aldol reaction of compound 2 stereoselectively produced the desired syn diastereomer (+/-)-5, which was resolved by a lipase-catalyzed acylation reaction. Under Mitsunobu conditions (Ph(3)P/DEAD), the syn aldol product (+)-5 led to the formation of trans-2,3-dimethyl chroman-4-one [(+)-3] with 94% ee, while the anti aldol product (+)-6 yielded both trans and cis derivatives (+)-3 and (+)-4 with 60% and 68% ee, respectively. Luche reduction on (+)-3 led to (+)-1 and (+)-calanolide B in a ratio of 9 : 1. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00433-8

文献信息

• Enantioselective total synthesis of anti HIV-1 active (+)-calanolide A through a quinine-catalyzed asymmetric intramolecular oxo-Michael addition
  作者：Tomohiro Tanaka、Takuya Kumamoto、Tsutomu Ishikawa

  DOI：10.1016/s0040-4039(00)01820-7

  日期：2000.12

  Enantioselective total synthesis of anti HIV-1 active (+)-calanolide A was achieved by a quinine-catalyzed asymmetric intramolecular oxo-Michael addition as a key step.

  通过奎宁催化的不对称分子内氧代-迈克尔加成反应是关键步骤，实现了抗HIV-1活性（+）-卡拉诺德A的对映选择性全合成。
• Sekino, Etsuko; Kumamoto, Takuya; Tanaka, Tomohiro, Journal of Organic Chemistry, 2004, vol. 69, # 8, p. 2760 - 2767
  作者：Sekino, Etsuko、Kumamoto, Takuya、Tanaka, Tomohiro、Ikeda, Tomoko、Ishikawa, Tsutomu

  DOI：——

  日期：——
• METHOD FOR THE PREPARATION OF (+/-)-CALANOLIDE A AND INTERMEDIATES THEREOF
  申请人：Sarawak Medichem Pharmaceuticals Inc.

  公开号：EP0775130B1

  公开（公告）日：2003-05-02
• Synthesis of (+)-calanolide A, an anti-HIV agent, Via enzyme-catalyzed resolution of the aldol products
  作者：Albert Khilevich、Aye Mar、Michael T. Flavin、John D. Rizzo、Lin Lin、Sergey Dzekhtser、Darko Brankovic、Heping Zhang、Wei Chen、Shuyuan Liao、David E. Zembower、Ze-Qi Xu

  DOI：10.1016/0957-4166(96)00433-8

  日期：1996.11

  The synthesis of (+)-calanolide A (1), an anti-HIV-1 agent, is described. A TiCl4-mediated aldol reaction of compound 2 stereoselectively produced the desired syn diastereomer (+/-)-5, which was resolved by a lipase-catalyzed acylation reaction. Under Mitsunobu conditions (Ph(3)P/DEAD), the syn aldol product (+)-5 led to the formation of trans-2,3-dimethyl chroman-4-one [(+)-3] with 94% ee, while the anti aldol product (+)-6 yielded both trans and cis derivatives (+)-3 and (+)-4 with 60% and 68% ee, respectively. Luche reduction on (+)-3 led to (+)-1 and (+)-calanolide B in a ratio of 9 : 1. Copyright (C) 1996 Elsevier Science Ltd
• Structure−Activity Modifications of the HIV-1 Inhibitors (+)-Calanolide A and (−)-Calanolide B
  作者：Deborah L. Galinis、Richard W. Fuller、Tawnya C. McKee、John H. Cardellina、Robert J. Gulakowski、James B. McMahon、Michael R. Boyd

  DOI：10.1021/jm9602827

  日期：1996.1.1

  The Delta(7,8) olefinic linkages within (+)-calanolide A (1) and (-)-calanolide B (2) were catalytically reduced to determine impact on the anti-HIV activity of the parent compounds. In addition, a series of structure modifications of the C-12 hydroxyl group in (-)-calanolide B was made to investigate the importance of that substituent to the HIV-1 inhibitory activity of these coumarins. A total of 14 analogs were isolated or prepared and compared to (+)-calanolide A and (-)-calanolide B in the NCI primary anti-HIV assay. While none of the compounds showed activity superior to the two unmodified leads, some structure-activity requirements were apparent from the relative anti-HIV potencies of the various analogs.