(2E)-ethyl <(2'S,5'S)-2'-methyl-5'-(1''-methylethenyl)cyclohexylidene>ethanoate | 142980-82-3

• 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: (2E)-ethyl <(2'S,5'S)-2'-methyl-5'-(1''-methylethenyl)cyclohexylidene>ethanoate
• 英文别名: ethyl (2E)-2-[(2S,5S)-2-methyl-5-prop-1-en-2-ylcyclohexylidene]acetate
• CAS: 142980-82-3
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: LGWFEFBOJFAECF-VSIAZPJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2E)-ethyl <(2'S,5'S)-2'-methyl-5'-(1''-methylethenyl)cyclohexylidene>ethanoate 在 咪唑 、 甲基锂 、 二异丁基氢化铝 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 25-羟基二氢速甾醇(2)
  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
• 作为产物：
  描述：

  右旋香芹酮 在 氨 、 lithium 、 sodium hydride 、 叔丁醇 作用下， 以 乙醚 为溶剂， 反应 27.5h， 生成 (2E)-ethyl <(2'S,5'S)-2'-methyl-5'-(1''-methylethenyl)cyclohexylidene>ethanoate
  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

• 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.
• 25-hydroxydihydrotachysterol2 an innovative synthesis of a key metabolite of dihydrotachysterol2
  作者：Jaap C. Hanekamp、Rob Boer Rookhuizen、Hendrik J.T. Bos、Lambert Brandsma

  DOI：10.1016/s0040-4020(01)85618-0

  日期：1992.1

  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.