(1R,3aR,7aR)-八氢-1-[(1R,2E,4S)-5-(甲氧基甲氧基)-1,4,5-三甲基-2-己烯-1-基]-7a-甲基-4H-茚-4-酮 | 100858-26-2

• 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,3aR,7aR)-八氢-1-[(1R,2E,4S)-5-(甲氧基甲氧基)-1,4,5-三甲基-2-己烯-1-基]-7a-甲基-4H-茚-4-酮
• 中文别名: (1R,3aR,7aR)-八氢-1-[(1R,2E,4S)-5-(甲氧基甲氧基)-1,4,5-三甲基-2-己烯-1-基]-7a-甲基-4氢-茚-4-酮
• 英文名称: (22E,24S)-de-A,B-25-<(methoxymethyl)oxy>ergost-22-en-8-one
• 英文别名: Grundmann's keton；(22E,24S)-de-A,B-25-[(methoxymethyl)oxy]ergost-22-en-8-one；(1R,3aR,7aR)-1-((2R,5S,E)-6-(methoxymethoxy)-5,6-dimethylhept-3-en-2-yl)-7a-methylhexahydro-1H-inden-4(2H)-one；(1R,3aR,7aR)-1-[(E,2R,5S)-6-(methoxymethoxy)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-one
• CAS: 100858-26-2
• 化学式: C₂₁H₃₆O₃
• 分子量: 336.515
• InChiKey: HSGIZUAUGQQEEU-KEODFZGNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3aR,7aR)-八氢-1-[(1R,2E,4S)-5-(甲氧基甲氧基)-1,4,5-三甲基-2-己烯-1-基]-7a-甲基-4H-茚-4-酮 在 bis-triphenylphosphine-palladium(II) chloride 喹啉 、 Lindlar's catalyst 、 ion-exchange resin AG 50W-X₄ 、 氢气 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 甲醇 、 异辛烷 、 正己烷 为溶剂， 反应 48.0h， 生成 25-二羟基维生素D2
  参考文献：
  名称：

  Studies on the opening of dioxanone and acetal templates and application to the synthesis of 1.alpha.,25-dihydroxyvitamin D2

  摘要：

  The Lewis-acid-mediated nucleophilic substitution of dioxanone and acetal templates for the construction of 25-hydroxylated side chains of vitamin D2 metabolites and analogs has been studied. As an application a highly stereoselective synthesis of 1alpha,25-dihydroxyvitamin D2 by the dienyne route is described.

  DOI：

  10.1021/jo00053a024
• 作为产物：
  描述：

  维生素D2 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 甲基锂 、 臭氧 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 112.17h， 生成 (1R,3aR,7aR)-八氢-1-[(1R,2E,4S)-5-(甲氧基甲氧基)-1,4,5-三甲基-2-己烯-1-基]-7a-甲基-4H-茚-4-酮
  参考文献：
  名称：

  25-hydroxydihydrotachysterol2 an innovative synthesis of a key metabolite of dihydrotachysterol2

  摘要：

  A new synthesis of 25-hydroxydihydrotachysterol2 is described The hydroxylated side-chain is constructed stereoselectively using a chiral Wittig reagent. The A-ring synthon is introduced utilising the Wittig-Horner method as developed by Lythgoe et al. The preparation of the metabolite is carried out in 18 steps.

  DOI：

  10.1016/s0040-4020(01)85618-0

文献信息

• Studies on the synthesis of side-chain hydroxylated metabolites of vitamin D. 2. Stereocontrolled synthesis of 25-hydroxyvitamin D2
  作者：F. Javier Sardina、Antonio Mourino、Luis Castedo

  DOI：10.1021/jo00358a018

  日期：1986.4
• A Synthesis of A-Ring Synthons for Dihydrotachysterols
  作者：Rob Boer Rookhuizen、Jaap C. Hanekamp、Hendrik J.T. Bos

  DOI：10.1016/s0040-4039(00)91693-9

  日期：1992.3

  Phosphine oxides 1 and 2, enantiomeric synthons for the preparation of dihydrotachysterols, were synthesized from the appropriate dihydrocarvones.
• A convergent approach to the dihydrotachysterol diene system. Application to the synthesis of dihydrotachysterol2 (DHT2), 25-hydroxydihydrotachysterol2 (25-OH-DHT2), 10(R),19-dihydro-(5E)-3-epivitamin D2 and 25-hydroxy-10(R),19-dihydro-(5E)-3-epivitamin D2
  作者：Miguel A. Maestro、Luis Castedo、Antonio Mourino

  DOI：10.1021/jo00045a038

  日期：1992.9

  Total synthesis of A-ring fragments of 10(S),19-dihydrovitamins D and 10(R),19-dihydro-(5E)-epivitamins D from (+)-(S)-carvone and (-)-(R)-carvone is described. These fragments were used for convergent synthesis of dihydrotachysterol2 (DHT2), 25-hydroxydihydrotachysterol2, 10(R),19-dihydro-(5E)-3-epivitamin D2, and 25-hydroxy-10(R),19-dihydro-(5E)-3-epivitamin D2.
• 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.