[1R-[1alpha,(1R*,2E,4S*),3abeta,7aalpha]]-八氢-1-(5-羟基-1,4,5-三甲基-2-己烯基)-7a-甲基-4H-茚-4-酮 | 95716-68-0

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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
• 中文名称: [1R-[1alpha,(1R*,2E,4S*),3abeta,7aalpha]]-八氢-1-(5-羟基-1,4,5-三甲基-2-己烯基)-7a-甲基-4H-茚-4-酮
• 中文别名: 帕立骨化醇中间体-16；帕立骨化醇中间体
• 英文名称: <1R<1β(R^*,E,S),3aα,7aβ>>-6-(Octahydro-7a-methyl-1H-4-oxoinden-1-yl)-2,3-dimethyl-4-hepten-2-ol
• 英文别名: 1R-<1α(1R*,2E,4S*),3aβ,7aα>-octahydro-1-(5-hydroxy-1,4,5-trimethyl-2-hexenyl)-7a-methyl-4H-inden-4-one；(1R,3aR,7aR)-1-((2R,5S,E)-6-hydroxy-5,6-dimethylhept-3-en-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-one；(1R,3aR,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 95716-68-0
• 化学式: C₁₉H₃₂O₂
• 分子量: 292.462
• InChiKey: QZJWXZGUOIMBAV-WXWTUHQWSA-N

物化性质

• 沸点：
  400.4±18.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1R-[1alpha,(1R*,2E,4S*),3abeta,7aalpha]]-八氢-1-(5-羟基-1,4,5-三甲基-2-己烯基)-7a-甲基-4H-茚-4-酮 在 正丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 20.08h， 生成 25-二羟基维生素D2
  参考文献：
  名称：

  Stereocontrolled total synthesis of 1.alpha.,25-dihydroxycholecalciferol and 1.alpha.,25-dihydroxyergocalciferol

  摘要：

  DOI：

  10.1021/jo00366a004
• 作为产物：
  描述：

  <3S-<3β,4α,3-<(2R*),1R*(1α,3aβ,4α,7aβ)>>>-3-<2-(octahydro-4-hydroxy-7a-methyl-1H-inden-1-yl)propyl>-2,5,5-trimethyl-4-isoxazolidinecarboxylic acid methyl ester 在 吡啶 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 pyridinium chlorochromate 、 碘甲烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 97.5h， 生成 [1R-[1alpha,(1R*,2E,4S*),3abeta,7aalpha]]-八氢-1-(5-羟基-1,4,5-三甲基-2-己烯基)-7a-甲基-4H-茚-4-酮
  参考文献：
  名称：

  Stereocontrolled total synthesis of 1.alpha.,25-dihydroxycholecalciferol and 1.alpha.,25-dihydroxyergocalciferol

  摘要：

  DOI：

  10.1021/jo00366a004

文献信息

• Two new approaches to the 25-hydroxy-vitamin D2 side chain
  作者：Stephen R. Wilson、Andrew E. Davey、Maria E. Guazzaroni

  DOI：10.1021/jo00033a021

  日期：1992.3

  Two approaches to the 25-hydroxy-vitamin D2 side chain have been developed based on the solvolysis of cyclopropylcarbinyl precursors. The first involves addition of trimethylcyclopropyllithium reagent 4 to a suitably protected C/D system 9. This reaction leads directly to cyclopropylcarbinols 10a,b which can be solvolyzed to the vitamin D2 side chain directly. The second approach uses an intermediate C/D system with a side chain allylic alcohol. Cyclopropanation of the allylic alcohol using Et2Zn/CH3CHI2 produces the same type of cyclopropylcarbinols 10a,b but in differing isomer ratios. Model studies and stereochemical differences in the two approaches are discussed.
• PROCESS FOR PRODUCTION OF INDENE DERIVATIVE, AND INTERMEDIATE FOR PRODUCTION OF THE DERIVATIVE
  申请人：MicroBiopharm Japan Co., Ltd.

  公开号：EP2011781B1

  公开（公告）日：2014-03-05
• Method For Preparing Indene Derivatives, And Intermediates For Preparation Of Derivatives
  申请人：Toyoda Asako

  公开号：US20090177002A1

  公开（公告）日：2009-07-09

  Indene derivatives that are utilizable as intermediates in the synthesis of the vitamin D 2 derivative paricalcitol, which is useful as pharmaceutical are efficiently prepared by subjecting a vitamin D 2 derivative such as 25-hydroxyvitamin D 2 to a two-steps oxidation reaction using an oxidizing agent such as potassium permanganates and sodium periodate in a suitable solvent such as methanol and ethanol.
• METHOD FOR PREPARING INDENE DERIVATIVES, AND INTERMEDIATES FOR PREPARATION OF DERIVATIVES
  申请人：TOYODA Asako

  公开号：US20120289723A1

  公开（公告）日：2012-11-15

  Indene derivatives that are utilizable as intermediates in the synthesis of the vitamin D 2 derivative paricalcitol, which is useful as pharmaceutical are efficiently prepared by subjecting a vitamin D 2 derivative such as 25-hydroxyvitamin D 2 to a two-steps oxidation reaction using an oxidizing agent such as potassium permanganates and sodium periodate in a suitable solvent such as methanol and ethanol.
• US9221753B2
  申请人：——

  公开号：US9221753B2

  公开（公告）日：2015-12-29