(-)-(1Z)-[(4R,5S,6S)-6-(β-D-glucopyranosyloxy)-5-hydroxy-4-methoxycyclohex-2-en-1-yliden]acetonitrile | 100757-58-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(1Z)-[(4R,5S,6S)-6-(β-D-glucopyranosyloxy)-5-hydroxy-4-methoxycyclohex-2-en-1-yliden]acetonitrile
• 英文别名: bauhinin；(-)-bauhinin；(2Z)-2-[(4R,5S,6S)-5-hydroxy-4-methoxy-6-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohex-2-en-1-ylidene]acetonitrile
• CAS: 100757-58-2
• 化学式: C₁₅H₂₁NO₈
• 分子量: 343.334
• InChiKey: LZYYZVIACZQHFH-VWNCQVFTSA-N

物化性质

• 沸点：
  647.1±55.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  153
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (-)-(1Z)-[(4R,5S,6S)-6-(β-D-glucopyranosyloxy)-5-hydroxy-4-methoxycyclohex-2-en-1-yliden]acetonitrile 在 盐酸 、 水 作用下， 反应 6.0h， 生成 bauhinilide
  参考文献：
  名称：

  紫荆花的化学成分。

  摘要：

  一种新的二氢黄酮醇糖苷二聚体6,6-bisastilbin（1）和一种新的含腈代谢物（Z）-5α，6β-二羟基-4β-甲氧基-2-环己烯-Δ1 ，α-乙腈（2）三种已知的类似物，bauhinin，bauhinilide，和dehydrodicatechin A，已从的乙醇提取物中分离紫荆罗非鱼。通过光谱和化学方法确定它们的结构。

  DOI：

  10.1080/10286020.2012.728209
• 作为产物：
  描述：

  2,3,4,6-tetra-O-isobutyryl-α-D-glucopyranosyl bromide 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 氢氟酸 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 19.17h， 生成 (-)-(1Z)-[(4R,5S,6S)-6-(β-D-glucopyranosyloxy)-5-hydroxy-4-methoxycyclohex-2-en-1-yliden]acetonitrile
  参考文献：
  名称：

  Total Synthesis of (−)-Bauhinin

  摘要：

  The total synthesis of the naturally occurring cyanoglucoside (-)-bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (-)-bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig-Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra-O-isobutyryl-D-glucosyl bromide 9 as the reagent in the Koenigs-Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (-)-bauhinin (1).

  DOI：

  10.1002/1522-2675(20010418)84:4<890::aid-hlca890>3.0.co;2-q

文献信息

• Total Synthesis of (−)-Bauhinin
  作者：Delphine Josien-Lefebvre、Guillaume Desmares、Claude Le Drian

  DOI：10.1002/1522-2675(20010418)84:4<890::aid-hlca890>3.0.co;2-q

  日期：2001.4.18

  The total synthesis of the naturally occurring cyanoglucoside (-)-bauhinin (1) was achieved starting from the optically pure oxatrinorbornenone 2 in 12 steps and 8% overall yield. The aglycone of (-)-bauhinin was easily obtained from the optically pure oxatrinorbornenone derivative 6 by a Wittig-Horner reaction followed by the opening of the oxa bridge. Glycosidation with tetra-O-isobutyryl-D-glucosyl bromide 9 as the reagent in the Koenigs-Knorr reaction afforded glucoside 10 in 58% yield, which, after photoisomerization and deprotection, gave (-)-bauhinin (1).
• Chemical constituents of<i>Bauhinia aurea</i>
  作者：Xiao-Ya Shang、Shuai Li、Su-Juan Wang、Yong-Chun Yang、Jian-Gong Shi

  DOI：10.1080/10286020.2012.728209

  日期：2012.10

  A new dihydroflavonol glycoside dimer 6,6-bisastilbin (1) and a new nitrile-containing metabolite (Z)-5α,6β-dihydroxy-4β-methoxy-2-cyclohexene-Δ1,α-acetonitrile (2), together with three known analogs, bauhinin, bauhinilide, and dehydrodicatechin A, have been isolated from an ethanol extract of Bauhinia aurea. Their structures were determined by spectroscopic and chemical methods.

  一种新的二氢黄酮醇糖苷二聚体6,6-bisastilbin（1）和一种新的含腈代谢物（Z）-5α，6β-二羟基-4β-甲氧基-2-环己烯-Δ1 ，α-乙腈（2）三种已知的类似物，bauhinin，bauhinilide，和dehydrodicatechin A，已从的乙醇提取物中分离紫荆罗非鱼。通过光谱和化学方法确定它们的结构。