<1R-<1α(R^*),3aβ,4α,7aα>>-octahydro-4-hydroxy-δ,7a-dimethyl-1H-indene-1-pentanoic acid ethyl ester | 146434-16-4

• 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: <1R-<1α(R^*),3aβ,4α,7aα>>-octahydro-4-hydroxy-δ,7a-dimethyl-1H-indene-1-pentanoic acid ethyl ester
• 英文别名: [1R-(1α(R^*),3aβ,4α,7aα)]-octahydro-4-hydroxy-δ,7a-dimethyl-1H-indene-1-pentanoic acid ethyl ester；Ethyl (R)-5-((1R,3aR,4S,7aR)-4-hydroxy-7a-methyloctahydro-1H-inden-1-yl)hexanoate；ethyl (5R)-5-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-1-yl]hexanoate
• CAS: 146434-16-4
• 化学式: C₁₈H₃₂O₃
• 分子量: 296.45
• InChiKey: NNSZDBXNFMACOX-KCYAQADSSA-N

物化性质

• 沸点：
  381.7±15.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <1R-<1α(R^*),3aβ,4α,7aα>>-octahydro-4-hydroxy-δ,7a-dimethyl-1H-indene-1-pentanoic acid ethyl ester 在 重铬酸吡啶 、 magnesium 作用下， 以 二氯甲烷 为溶剂， 反应 72.83h， 生成 (1R,3aR,7aR)-1-{(1R)-1,5-dimethyl-5-[(trimethylsilyl)oxy]hexyl}-7a-methyloctahydro-4H-inden-4-one
  参考文献：
  名称：

  Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1.alpha.,25-dihydroxyvitamin D3 CD ring

  摘要：

  A novel chiral synthesis of the CD-ring 2 of 1alpha,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100-degrees-C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.

  DOI：

  10.1021/jo00058a032
• 作为产物：
  描述：

  <1R-(1α,7aα)>-1-<(1R)-3-<(tert-butyldiphenylsilyl)oxy>-1-methylpropyl>-1,2,5,6,7,7a-hexahydro-7a-methyl-4H-inden-4-one 在 palladium on activated charcoal 、 RhCl(PPh₃)3 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 cerium(III) chloride 、 四丁基氟化铵 、 氢气 、 potassium hydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 paraffin 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 66.84h， 生成 <1R-<1α(R^*),3aβ,4α,7aα>>-octahydro-4-hydroxy-δ,7a-dimethyl-1H-indene-1-pentanoic acid ethyl ester
  参考文献：
  名称：

  Stereoselective synthesis of cyclopentanones by reductive cleavage of 6-oxonorbornane-2-carboxylates and its application to the synthesis of 1.alpha.,25-dihydroxyvitamin D3 CD ring

  摘要：

  A novel chiral synthesis of the CD-ring 2 of 1alpha,25-dihydroxyvitamin D3 (1a) is described. The optically active D-ring keto ester 3c was prepared by reductive cleavage of 6-oxonorbornane-2-carboxylate 4c with lithium naphthalenide. 1,2-Transposition of enone 15, which was obtained by Robinson annulation of 14, was accomplished via thermolysis of the allylic carbonate 29 at 100-degrees-C to give enone 16. Reduction of ketone 16 with NaBH4-CeCl3 followed by hydrogenation with RhCl-(PPh3)3 catalyst gave trans-indanol 32, which was transformed to intermediate 2.

  DOI：

  10.1021/jo00058a032

文献信息

• Vitamin D receptor agonist/histone deacetylase inhibitor molecular hybrids
  作者：Marc Lamblin、Basel Dabbas、Russell Spingarn、Rodrigo Mendoza-Sanchez、Tian-Tian Wang、Beum-Soo An、Dao Chao Huang、Richard Kremer、John H. White、James L. Gleason

  DOI：10.1016/j.bmc.2010.03.078

  日期：2010.6.1

  Incorporation of zinc-binding groups into the side-chain of 1 alpha, 25-dihydroxyvitamin D-3 (1,25D) fully bifunctional hybrid molecules which act both as vitamin D receptor agonists and histone deacetylase inhibitors. These bifunctional hybrids display in vitro antiproliferative activity against the AT84 squamous carcinoma cell line while lacking the in vivo hypercalcemic effects of 1,25D. (C) 2010 Elsevier Ltd. All rights reserved.