(3R,4R,5S)-4-(3-hydroxypropyl)oct-1-en-7-yne-3,5-diol | 769126-87-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,4R,5S)-4-(3-hydroxypropyl)oct-1-en-7-yne-3,5-diol
• 英文别名: (3R,4S,5R)-4-(3-hydroxypropyl)oct-1-en-7-yne-3,5-diol
• CAS: 769126-87-6
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: ATUCMWBJNBMCQU-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R,5S)-4-(3-hydroxypropyl)oct-1-en-7-yne-3,5-diol 在 四(三苯基膦)钯 2,6-二甲基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  24,24-Dimethylvitamin D3-26,23-lactones and their 2α-functionalized analogues as highly potent VDR antagonists

  摘要：

  Novel vitamin D receptor (VDR) antagonists, 24,24-dimethyl-1alpha-hydroxyvitamin D-3-26,23-lactones (8 and 9) and their C2alpha functionalized analogues (8a-c and 9a-c) were efficiently synthesized and their biological activities were evaluated. The construction of vitamin D-3 triene skeleton was achieved by palladium-catalyzed alkenylative cyclization of A-ring precursor enyne (22 and 22a-c) with CD-ring bromoolefin having a 24,24-dimethyl-alpha-methylene-gamma-lactone unit on the side chain (13 and 14). The CD-ring precursors 13 and 14 were prepared by using chromium-mediated allylation of the aldehyde 10 derived from vitamin D-2. On the other hand, the A-ring enyne having 2alpha-(3-hydroxypropyl) group (22b) was newly synthesized from epoxide 15 using regio- and stereoselective alkylation methodology. The potency of the antagonistic activity of the newly designed analogues (8 and 9) increased up to 12 times that of TEI-9647 (2). Furthermore, introduction of the three motifs, that is, a methyl (8a and 9a), an omega-hydroxypropyl (8b and 9b) or an omega-hydroxypropoxyl group (8c and 9c) into the C2alpha position of 8 and 9, respectively, resulted in remarkable enhancement, up to 89 times, of the antagonistic activity on VDR. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.113
• 作为产物：
  描述：

  methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 吡啶 、 2,6-二甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 硼烷四氢呋喃络合物 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium cyanoborohydride 、 barium carbonate 、 锌 作用下， 以 四氢呋喃 、 丙醇 、 四氯化碳 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 96.5h， 生成 (3R,4R,5S)-4-(3-hydroxypropyl)oct-1-en-7-yne-3,5-diol
  参考文献：
  名称：

  24,24-Dimethylvitamin D3-26,23-lactones and their 2α-functionalized analogues as highly potent VDR antagonists

  摘要：

  Novel vitamin D receptor (VDR) antagonists, 24,24-dimethyl-1alpha-hydroxyvitamin D-3-26,23-lactones (8 and 9) and their C2alpha functionalized analogues (8a-c and 9a-c) were efficiently synthesized and their biological activities were evaluated. The construction of vitamin D-3 triene skeleton was achieved by palladium-catalyzed alkenylative cyclization of A-ring precursor enyne (22 and 22a-c) with CD-ring bromoolefin having a 24,24-dimethyl-alpha-methylene-gamma-lactone unit on the side chain (13 and 14). The CD-ring precursors 13 and 14 were prepared by using chromium-mediated allylation of the aldehyde 10 derived from vitamin D-2. On the other hand, the A-ring enyne having 2alpha-(3-hydroxypropyl) group (22b) was newly synthesized from epoxide 15 using regio- and stereoselective alkylation methodology. The potency of the antagonistic activity of the newly designed analogues (8 and 9) increased up to 12 times that of TEI-9647 (2). Furthermore, introduction of the three motifs, that is, a methyl (8a and 9a), an omega-hydroxypropyl (8b and 9b) or an omega-hydroxypropoxyl group (8c and 9c) into the C2alpha position of 8 and 9, respectively, resulted in remarkable enhancement, up to 89 times, of the antagonistic activity on VDR. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.113

文献信息

• VITAMIN D3 LACTAM DERIVATIVE
  申请人：Nakamura Yuko

  公开号：US20110207944A1

  公开（公告）日：2011-08-25

  Compound represented by formula (1) or a pharmaceutically acceptable solvate thereof, useful for treating or preventing Paget's disease of bone, hypercalcaemia, osteoporosis or asthma. (1) R 1 represents a C 1 -C 6 alkyl group or C 7 -C 15 aralkyl group (the aromatic ring of which can be substituted by a C 1 -C 6 alkyl group, C 1 -C 6 alkoxy group, a hydroxyl group, a halogenatom or a trifluoromethyl group), R 2 represents a C 1 -C 6 alkyl group, and R 3 represents a C 1 -C 6 alkyl or alkoxy group, which can be substituted with a hydroxyl group.

  由以下化学式（1）表示的化合物或其药用可接受的溶剂盐，用于治疗或预防骨的帕吉特病、高钙血症、骨质疏松症或哮喘。其中，R1代表C1-C6烷基或C7-C15芳基烷基（其芳香环可以被C1-C6烷基、C1-C6甲氧基、一个羟基、一个卤原子或三氟甲基取代），R2代表C1-C6烷基，R3代表C1-C6烷基或烷氧基，可以被一个羟基取代。