6-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2,10-dimethyl-undecane-2,10-diol | 478944-14-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 6-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2,10-dimethyl-undecane-2,10-diol
• 英文别名: 6-[(1R,3aR,4E,7aR)-4-(bromomethylidene)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2,10-dimethylundecane-2,10-diol
• CAS: 478944-14-8
• 化学式: C₂₄H₄₃BrO₂
• 分子量: 443.508
• InChiKey: AKURMFGVOJREJM-BLDPOXIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2,10-dimethyl-undecane-2,10-diol 在 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 14.0h， 生成 (1R,2S,3S)-5-[2-[(1R,3aS,7aR)-1-[5-Hydroxy-1-(4-hydroxy-4-methyl-pentyl)-5-methyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-2-(3-hydroxy-propyl)-4-methylene-cyclohexane-1,3-diol
  参考文献：
  名称：

  Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain: marked cell differentiation activity

  摘要：

  The 2alpha-methyl-, 2alpha-(3-hydroxypropyl)-, and 2alpha-(3-hydroxypropoxy)-derivatives of the 'double side chain' analogue of 1alpha,25-dihydroxyvitamin D-3 were synthesized using Trost A-ring/CD-ring connective strategy. Regarding the requisite A-ring building blocks, a new, high yield and stereoselective route to the 2alpha-methyl compound starting from D-glucose was developed. All three new analogues showed potent HL-60 cancer cell differentiation activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00722-9
• 作为产物：
  描述：

  溴甲基三苯基溴化磷 、 [1S-(1α,3aβ,4α,7aα)]-octahydro-1-[5-hydroxy-1-(4-hydroxy-4-methylpentyl)-5-methylhexyl]-7a-methyl-4H-inden-4-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以68%的产率得到6-{(1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2,10-dimethyl-undecane-2,10-diol
  参考文献：
  名称：

  Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain: marked cell differentiation activity

  摘要：

  The 2alpha-methyl-, 2alpha-(3-hydroxypropyl)-, and 2alpha-(3-hydroxypropoxy)-derivatives of the 'double side chain' analogue of 1alpha,25-dihydroxyvitamin D-3 were synthesized using Trost A-ring/CD-ring connective strategy. Regarding the requisite A-ring building blocks, a new, high yield and stereoselective route to the 2alpha-methyl compound starting from D-glucose was developed. All three new analogues showed potent HL-60 cancer cell differentiation activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00722-9

文献信息

• Synthesis and testing of 2α-Modified 1α,25-Dihydroxyvitamin D3 analogues with a double side chain: marked cell differentiation activity
  作者：Yoshitomo Suhara、Atsushi Kittaka、Seishi Kishimoto、Martin J. Calverley、Toshie Fujishima、Nozomi Saito、Takayuki Sugiura、Keizo Waku、Hiroaki Takayama

  DOI：10.1016/s0960-894x(02)00722-9

  日期：2002.11

  The 2alpha-methyl-, 2alpha-(3-hydroxypropyl)-, and 2alpha-(3-hydroxypropoxy)-derivatives of the 'double side chain' analogue of 1alpha,25-dihydroxyvitamin D-3 were synthesized using Trost A-ring/CD-ring connective strategy. Regarding the requisite A-ring building blocks, a new, high yield and stereoselective route to the 2alpha-methyl compound starting from D-glucose was developed. All three new analogues showed potent HL-60 cancer cell differentiation activity. (C) 2002 Elsevier Science Ltd. All rights reserved.