(1S)-1-(furan-2-yl)-3-methylbutan-1-ol | 1268341-12-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (1S)-1-(furan-2-yl)-3-methylbutan-1-ol
• CAS: 1268341-12-3
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: WPTNAKBTQXBXLX-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  11.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  33.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S)-1-(furan-2-yl)-3-methylbutan-1-ol 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 2-硝基苯磺酰肼 、 sodium acetate 、 碳酸氢钠 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 37.0h， 生成 3-[(3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-3-[(2R,5R,6S)-5-hydroxy-6-(2-methylpropyl)oxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
  参考文献：
  名称：

  C5′-Alkyl Substitution Effects on Digitoxigenin α-l-Glycoside Cancer Cytotoxicity

  摘要：

  A highly regio- and stereoselective asymmetric synthesis of various CS'-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5'-methyl group in both alpha-L-rhamnose and cc-L-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5'-stereocenter.

  DOI：

  10.1021/ml100291n
• 作为产物：
  描述：

  异戊酸 在 (1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine-ruthenium(mesitylene) 、 正丁基锂 、 sodium formate 、 十六烷基三甲基溴化铵 作用下， 以 正己烷 、 水 为溶剂， 反应 24.0h， 生成 (1S)-1-(furan-2-yl)-3-methylbutan-1-ol
  参考文献：
  名称：

  C5′-Alkyl Substitution Effects on Digitoxigenin α-l-Glycoside Cancer Cytotoxicity

  摘要：

  A highly regio- and stereoselective asymmetric synthesis of various CS'-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5'-methyl group in both alpha-L-rhamnose and cc-L-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5'-stereocenter.

  DOI：

  10.1021/ml100291n

文献信息

• Chloroperoxidase-Catalyzed Achmatowicz Rearrangements
  作者：Daniel Thiel、Fabian Blume、Christina Jäger、Jan Deska

  DOI：10.1002/ejoc.201800333

  日期：2018.6.7

  HUOM! TAMA MANUSKA ON TILASSA CLOSED KUNNES ARTIKKELI ON JULKAISTU JA JULKAISUVIIVE MAARITELTY KUSTANTAJAN JULKAISUPAIVASTA ALKAEN. The manuscript is "closed" until the article has been published and the embargo date can be defined.

  呼！蒂拉萨岛上的 TAMA MANUSKA 关闭了 JULKAISTU JA JULKAISUVIIVE MAARITELTY KUSTANTAJAN JULKAISUPAIVASTA ALKAEN 的 KUNNES ARTIKKELI。在文章发表并且可以确定禁运日期之前，手稿处于“关闭”状态。
• C5′-Alkyl Substitution Effects on Digitoxigenin α-<scp>l</scp>-Glycoside Cancer Cytotoxicity
  作者：Hua-Yu Leo Wang、Bulan Wu、Qi Zhang、Sang-Woo Kang、Yon Rojanasakul、George A. O’Doherty

  DOI：10.1021/ml100291n

  日期：2011.4.14

  A highly regio- and stereoselective asymmetric synthesis of various CS'-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5'-methyl group in both alpha-L-rhamnose and cc-L-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5'-stereocenter.